The Undertaker

Mark William Calaway was born in Houston, Texas, on March 24, 1965,{{cite web|url=https://familysearch.org/search/collection/results?count=20&query=%2Bgivenname%3AMark~%20%2Bsurname%3ACalaway~%20%2Bbirth_year%3A1965-1965~%20%2Bgender%3AM&collection_id=1949342|title=Texas Birth Index, 1903–1997|work=FamilySearch|access-date=December 29, 2016|archive-date=December 29, 2016|archive-url=https://web.archive.org/web/20161229172259/https://familysearch.org/search/collection/results?count=20&query=%2Bgivenname%3AMark~%20%2Bsurname%3ACalaway~%20%2Bbirth_year%3A1965-1965~%20%2Bgender%3AM&collection_id=1949342|url-status=live}}New Wave Wrestling, February 1995, issue 15, p.15.{{cite web|url=https://www.sbnation.com/lookit/2016/3/24/11298454/wwe-photo-happy-birthday-undertaker-the-frowniest-face|title=Not even a birthday cake can make the Undertaker smile|work=SB Nation|date=March 24, 2016|access-date=January 24, 2019|archive-date=June 29, 2020|archive-url=https://web.archive.org/web/20200629065037/https://www.sbnation.com/lookit/2016/3/24/11298454/wwe-photo-happy-birthday-undertaker-the-frowniest-face|url-status=live}} the son of Frank Compton Calaway (died July 2003) and Betty Catherine Truby.{{citation needed|date=March 2023}} He has four older brothers named David, Michael, Paul, and Timothy (died March 2020, aged 63).{{Cite web|title=Timothy Calaway obituary|url=https://www.legacy.com/obituaries/statesman/obituary.aspx?n=timothy-calaway&pid=195910043&fhid=12067|last=Calaway|first=Timothy|date=March 24, 2020|website=Legacy|access-date=May 12, 2020|archive-date=June 30, 2020|archive-url=https://web.archive.org/web/20200630024620/https://www.legacy.com/obituaries/statesman/obituary.aspx?n=timothy-calaway&pid=195910043&fhid=12067|url-status=live}} He attended Waltrip High School, where he was a member of the football and basketball teams. He graduated in 1983 and began studying on a basketball scholarship at Angelina College in Lufkin, Texas. In 1985, he enrolled in Texas Wesleyan University in Fort Worth, Texas, where he majored in sport management and played as a center for the Rams in the 1985–1986 season. In 1986, Calaway dropped out of university to focus on a career in sports and briefly considered playing professional basketball in Europe, before deciding to focus on professional wrestling.{{cite web|url=http://hs.houstonisd.org/WaltripHS/TriviaFolder/trivia.htm|title=Waltrip trivia page|publisher=Waltrip High School|access-date=March 27, 2007|archive-date=August 31, 2012|archive-url=https://web.archive.org/web/20120831194046/http://hs.houstonisd.org/WaltripHS/TriviaFolder/trivia.htm|url-status=live}}{{cite book|author=Tim O'Shei|title=Undertaker|url=https://books.google.com/books?id=u-6RZ9qx5RkC&pg=PA8|date=July 1, 2009|publisher=Capstone|isbn=978-1-4296-3351-2|pages=8–11}}{{cite book|author=Jennifer Bringle|title=The Undertaker: Master of Pain|url=https://books.google.com/books?id=TM38w278TJIC&pg=PA7|date=December 2011|publisher=The Rosen Publishing Group|isbn=978-1-4488-5536-0|pages=7–8}}{{cite book|author=A. R. Schaefer|title=The Undertaker: Pro Wrestler Mark Callaway|url=https://books.google.com/books?id=R7IEM_euj28C&pg=PA12|date=June 2002|publisher=Capstone|isbn=978-0-7368-1312-9|pages=12–13}}

{{Professional wrestling sidebar}}Calaway began training under Buzz Sawyer in late 1986;{{cite episode|title=The Undertaker|series=Steve Austin's Broken Skull Sessions|network=WWE Network|date=November 24, 2019|minutes=3–8 & 20}}{{cite AV media|date=2001|title=Undertaker: This Is My Yard|medium=DVD|time=1:38|publisher=WWE Home Video}} he disliked Sawyer, who reportedly lacked commitment and provided a limited education.{{cite web|url=https://prowrestling.net/artman/publish/WWE/Former_WWE_manager_Paul_Bearer_comments_on_how_he_was_paired_with_Undertaker_managing_Taker_before_he_was_given_the_gimmick_interviewing_Hulk_Hogan_and_Ric_Flair_on_The_Funeral_Parlor_printer.shtml|title=Former WWE manager Paul Bearer|date=May 18, 2010|website=Pro Wrestling Dot Net|access-date=November 28, 2019|archive-date=December 10, 2019|archive-url=https://web.archive.org/web/20191210160323/https://prowrestling.net/artman/publish/WWE/Former_WWE_manager_Paul_Bearer_comments_on_how_he_was_paired_with_Undertaker_managing_Taker_before_he_was_given_the_gimmick_interviewing_Hulk_Hogan_and_Ric_Flair_on_The_Funeral_Parlor_printer.shtml|url-status=live}} Calaway learned "on the job" thereafter.{{cite web|url=https://www.pwinsider.com/article/141618/eric-bischoffs-place-in-history-undertaker-paul-bearer-hate-watching-pro-wrestling-the-gobbledy-gookers-return-and-more.html?p=1|title=Eric Bischoff's place in history, Undertaker & Paul Bearer, hate-watching pro wrestling, the Gobbledy Gooker's return and more|last=Johnson|first=Mike|date=November 25, 2020|website=PWInsider|access-date=November 25, 2020|archive-date=September 10, 2021|archive-url=https://web.archive.org/web/20210910215546/https://www.pwinsider.com/article/141618/eric-bischoffs-place-in-history-undertaker-paul-bearer-hate-watching-pro-wrestling-the-gobbledy-gookers-return-and-more.html?p=1|url-status=live}} Performing under a mask as Texas Red, Calaway wrestled his first match on June 26, 1987, for World Class Championship Wrestling (WCCW), losing to Bruiser Brody at the Dallas Sportatorium.{{cite episode|title=VIP audio 12/1|url=https://www.pwtorch.com/site/2019/12/01/vip-audio-12-1-the-fix-w-todd-martin-reviews-of-aew-dynamite-nxt-on-usa-smackdown-including-fiend-bryan-survivor-series-follow-up-jericho-celebration-plus-mailbag-on-jakes-cobra-bit/|series=The Fix with Todd Martin|first=Wade|last=Keller|author-link=Wade Keller|date=December 1, 2019|minutes=76|access-date=December 8, 2019|archive-date=September 10, 2021|archive-url=https://web.archive.org/web/20210910215546/https://www.pwtorch.com/site/2019/12/01/vip-audio-12-1-the-fix-w-todd-martin-reviews-of-aew-dynamite-nxt-on-usa-smackdown-including-fiend-bryan-survivor-series-follow-up-jericho-celebration-plus-mailbag-on-jakes-cobra-bit/|url-status=live}}{{Subscription required|via=PWTorch.com}}{{cite web|url=https://www.cagematch.net//?id=2&nr=761&page=4&s=2300|title=Undertaker: Matches (p.24, archived)|website=Cagematch.net|access-date=December 8, 2019|archive-url=https://web.archive.org/web/20191208171321/https://www.cagematch.net//?id=2&nr=761&page=4&s=2300|archive-date=December 8, 2019}} He was accompanied to the ring by Percival "Percy" Pringle III, who would later serve as his manager in the WWF as Paul Bearer.{{cite web|url=https://www.cagematch.net//?id=1&nr=249359|title=Event: 26.06.1987|website=Cagematch.net|access-date=December 8, 2019|archive-date=September 10, 2021|archive-url=https://web.archive.org/web/20210910215555/https://www.cagematch.net//?id=1&nr=249359|url-status=live}} Two myths have circulated regarding Calaway's beginnings in the industry, the first being that he made his in-ring debut in 1984, and the second being that he was trained by former WCCW colleague Don Jardine (aka The Spoiler).{{cite web|url=https://www.pwinsider.com/article/141568/can-a-wrestler-get-the-leverage-needed-to-have-the-upper-hand-against-wwe-training-taker-drew-is-scary-and-more.html?p=1|title=Can a wrestler get the leverage needed to have the upper hand against WWE, training Taker, Drew is scary and more|last=Scherer|first=Dave|author-link=Dave Scherer|date=November 24, 2020|website=PWInsider|access-date=November 25, 2020|archive-date=September 10, 2021|archive-url=https://web.archive.org/web/20210910215546/https://www.pwinsider.com/article/141568/can-a-wrestler-get-the-leverage-needed-to-have-the-upper-hand-against-wwe-training-taker-drew-is-scary-and-more.html?p=1|url-status=live}}{{cite episode|title=VIP audio 12/12|url=https://www.pwtorch.com/site/2019/12/12/vip-audio-12-12-the-fix-w-todd-martin-mailbag-pt-2-of-2-should-aew-have-a-single-booker-is-nxt-ready-to-tour-outside-of-full-sail-which-macho-man-outfit-was-best-plus-wwe-releases/|series=The Fix with Todd Martin|first=Wade|last=Keller|author-link=Wade Keller|date=December 12, 2019|minutes=18|access-date=December 13, 2019|archive-date=December 13, 2019|archive-url=https://web.archive.org/web/20191213233101/https://www.pwtorch.com/site/2019/12/12/vip-audio-12-12-the-fix-w-todd-martin-mailbag-pt-2-of-2-should-aew-have-a-single-booker-is-nxt-ready-to-tour-outside-of-full-sail-which-macho-man-outfit-was-best-plus-wwe-releases/|url-status=live}}{{Subscription required|via=PWTorch.com}} While never trained by Jardine, Calaway was an admirer of his work and would emulate Jardine's top rope walk."Episode 14: 1990 Survivor Series". Something to Wrestle with Bruce Prichard. November 4, 2016. c. 150 minutes in (commercials vary between locations).{{cite book|last=Schire|first=George|date=2010|title=Minnesota's Golden Age of Wrestling|publisher=Minnesota Historical Society Press|page=200|isbn=978-0873516204}} PWInsider{{'}}s Mike Johnson stated, "Undertaker using some of Jardine's style eventually morphed into this story that he was trained by Jardine."

He wrestled in Durban, South Africa on August 22, 1987, as "Texas Red Jack", losing to Tiger Singh.{{cite web |title=Matches |url=https://www.cagematch.net/?id=2&nr=761&page=4&year=1987&promotion=2383 |website=www.cagematch.net |access-date=August 1, 2023 |archive-url=https://web.archive.org/web/20230716003640/https://www.cagematch.net/?id=2&nr=761&page=4&year=1987&promotion=2383 |archive-date=July 16, 2023 |language=en |date=August 22, 1987 |url-status=live}} He would also wrestle in prison shows under the name Boris Dragu, a Russian grave digger.

In 1988, Calaway developed a military gimmick named The Commando. Under this persona, he mainly wrestled in the Chicago area for Central Illinois Wrestling. He would also have a brief stint in Georgia for Southern Championship Wrestling.

By the end of 1988, Calaway joined the Continental Wrestling Association, wrestling under several gimmicks. On February 2, 1989, managed by Dutch Mantel, he was reintroduced as The Master of Pain, a former murderer.{{Cite web|url=https://bleacherreport.com/articles/2548866-undertakers-early-career-a-reminder-of-how-vital-finding-the-right-gimmick-is|title=Undertaker's Early Career a Reminder of How Vital Finding the Right Gimmick Is|last=Dilbert|first=Ryan|website=Bleacher Report|access-date=February 16, 2019|archive-date=September 10, 2021|archive-url=https://web.archive.org/web/20210910220059/https://bleacherreport.com/articles/2548866-undertakers-early-career-a-reminder-of-how-vital-finding-the-right-gimmick-is|url-status=live}} On April 1, The Master of Pain won his first professional wrestling championship by defeating Jerry Lawler for the USWA Unified World Heavyweight Champion. Just over three weeks had passed when Lawler became the first man to pin him, giving it back to him. While performing as The Punisher upon returning to Dallas, Calaway won the USWA Texas Heavyweight Championship on October 5, 1989, when Eric Embry forfeited the title.{{cite web|url=http://www.wrestling-titles.com/us/tx/tx-h.html|title=Texas Heavyweight Title history|publisher=Wrestling-Titles.com|access-date=April 9, 2008|archive-date=November 13, 2015|archive-url=https://web.archive.org/web/20151113145609/http://www.wrestling-titles.com/us/tx/tx-h.html|url-status=live}}

{{see also|The Skyscrapers}}

By the end of 1989, Calaway joined World Championship Wrestling (WCW) as a villain and adopted the ring name "Mean Mark" Callous, a name devised for him by Terry Funk.{{cite book|last1=Funk|first1=Terry|author-link1=Terry Funk|last2=Williams|first2=Scott|title=Terry Funk: More Than Just Hardcore|year=2006|publisher=Sports Publishing|location=Champaign, IL|isbn=1-59670-159-5|page=198}} Retrieved on April 18, 2018 He was portrayed as a sinister force, wearing predominantly black ring attire and was described by commentator Jim Ross as having a fondness for pet snakes and the music of Ozzy Osbourne.WCW/NWA Capital Combat (VHS). Turner Home Entertainment. 1990. Callous was promptly drafted into The Skyscrapers tag team to replace a legitimately injured Sid Vicious, and made his debut on January 3, 1990, in a match later televised against Agent Steel and Randy Harris.{{cite web |url=http://www.thehistoryofwwe.com/wcw90.htm |title=WCW 1990 |website=thehistoryofwwe.com |access-date=January 9, 2022 |archive-date=March 23, 2019 |archive-url=https://web.archive.org/web/20190323005922/http://www.thehistoryofwwe.com/wcw90.htm |url-status=live }} The new team gained some notoriety at Clash of the Champions X when they beat down The Road Warriors after their match.{{cite web|url=http://www.prowrestlinghistory.com/supercards/usa/wcw/clash.html#X|title=NWA Clash of the Champions Results (X)|access-date=April 16, 2007|website=prowrestlinghistory.com|archive-date=March 31, 2013|archive-url=https://web.archive.org/web/20130331044030/http://www.prowrestlinghistory.com/supercards/usa/wcw/clash.html#X|url-status=live}} However, Callous's partner Dan Spivey left WCW days before their Chicago Street Fight against the Road Warriors at WrestleWar. Callous and a replacement masked Skyscraper were defeated in the street fight and the team broke up soon afterwards.{{cite web|url=http://www.prowrestlinghistory.com/supercards/usa/wcw/w-war.html#90|title=NWA WrestleWar Results (1990)|access-date=April 16, 2007|website=prowrestlinghistory.com|archive-date=November 2, 2013|archive-url=https://web.archive.org/web/20131102025143/http://www.prowrestlinghistory.com/supercards/usa/wcw/w-war.html#90|url-status=live}} Now a singles wrestler, Callous took on the guidance of Paul E. Dangerously (Paul Heyman).

Calaway later began to question his future in WCW after being told by company booker, Ole Anderson, during contract renewal discussions that nobody would ever pay money to watch him perform. It was in response to this that Calaway made numerous efforts to join the World Wrestling Federation, going to many lengths to land a meeting with Vince McMahon. However, accessing and securing an interview with McMahon was described by Calaway as a despairing task.{{cite news|url=https://books.google.com/books?id=iZqdBgAAQBAJ&dq=suburban+commando+movie+undertaker+vince+mcmahon&pg=PA224|title=The Complete WWF Video Guide Volume 5 (p. 224)|access-date=February 12, 2022|work=Lulu|last1=Maughan|first1=Lee|last2=Furious|first2=Arnold|last3=Dixon|first3=James|date=March 29, 2014|isbn=9781291816938|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003419/https://books.google.com/books?id=iZqdBgAAQBAJ&dq=suburban+commando+movie+undertaker+vince+mcmahon&pg=PA224|url-status=live}}

Among routes Calaway took to land a meeting with McMahon was trying to convince individuals acquainted with McMahon or already existing WWF talent to recommend him into the WWF, such as Hulk Hogan, Paul Heyman, and Bruce Prichard, crediting the latter two for arranging the meeting at McMahon's mansion.{{cite news|url=https://www.youtube.com/watch?v=pzseicO0FQQ|title=The Origins of The Undertaker Character|work=The Joe Rogan Experience|access-date=March 8, 2022|last=Rogan|first=Joe|date=2020|archive-date=March 8, 2022|archive-url=https://web.archive.org/web/20220308141024/https://www.youtube.com/watch?v=pzseicO0FQQ|url-status=live}}

Calaway immediately gave notice to WCW before the interview took place. McMahon initially declined to hire Calaway; however, several days later the owner pitched the idea of an "Old West Undertaker", a concept he had intended to create for several years but had never found an appropriate wrestler to play the part.

Calaway's final WCW match was on September 7 at a WorldWide taping in Amarillo, Texas in which he defeated Dave Johnson. During his time in WCW, Calaway briefly wrestled in New Japan Pro-Wrestling (NJPW) as "Punisher" Dice Morgan. After leaving WCW, he briefly returned to the USWA to participate in a tournament to determine the new USWA Unified World Heavyweight Champion; Calaway defeated Bill Dundee in the first round, but lost to Jerry Lawler in the quarterfinals.

In October 1990, Calaway signed with the World Wrestling Federation (WWF), set to portray the "brainchild" of McMahon that he had assigned to him, originally entitled Kane the Undertaker ("Kane" later added on to "the Undertaker" moniker by the time of his arrival at the urgings of Bruce Prichard, who had always desired a Cain and Abel effect for his character).{{cite magazine|url=https://www.si.com/extra-mustard/2016/11/23/week-wrestling-kevin-nash-on-diesel-creation-of-undertaker|title=Week in Wrestling: Kevin Nash on Diesel; creation of Undertaker; Gobbledy Gooker speaks|access-date=August 28, 2022|magazine=Sports Illustrated|last=Barrasso|first=Justin|date=November 23, 2016|archive-date=August 28, 2022|archive-url=https://web.archive.org/web/20220828172502/https://www.si.com/extra-mustard/2016/11/23/week-wrestling-kevin-nash-on-diesel-creation-of-undertaker|url-status=live}} Despite Calaway's perplexed, pessimistic feelings about McMahon's gimmick idea, he was readily accepting of the role, feeling anything better than the laughingstock gimmicks of that time, such as The Gobbledy Gooker. Kane the Undertaker was characterized as a menacing derivative of the Wild West undertakers depicted in television westerns. Resulting from that, this first edition of the Undertaker's series of Deadman incarnations{{cite news|url=https://books.google.com/books?id=_tCGDwAAQBAJ&dq=suburban+commando+undertaker+vince+mcmahon+old+west&pg=PT245|title=Pro Wrestling FAQ: All That's Left to Know About the World's Most Entertaining Spectacle|access-date=February 12, 2022|work=Backbeat|last=Solomon|first=Brian|date=January 1, 2015|isbn=9781617136283|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003413/https://books.google.com/books?id=_tCGDwAAQBAJ&dq=suburban+commando+undertaker+vince+mcmahon+old+west&pg=PT245|url-status=live}} has been distinguished in external media as "The Old West Mortician".{{cite news|url=https://books.google.com/books?id=A5DqCgAAQBAJ&dq=the+undertaker+old+west+mortician+sid&pg=PT225|title=Pro Wrestling FAQ: All That's Left To Know About The World's Most Entertaining Spectacle|access-date=February 19, 2022|work=Backbeat|last=Solomon|first=Brian|date=January 1, 2015|isbn=9781617136276}}{{cite news|url=https://books.google.com/books?id=TPSKDwAAQBAJ&dq=western+mortician+the+undertaker+version+wwf&pg=PT104|title=Convergent Wrestling: Participatory Culture, Transmedia Storytelling, and Intertextuality in the Squared Circle|access-date=February 19, 2022|work=Taylor & Francis|last1=Reinhard|first1=CarrieLynn|last2=Olson|first2=Christopher|date=March 4, 2019|isbn=9781351233965|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003416/https://books.google.com/books?id=TPSKDwAAQBAJ&dq=western+mortician+the+undertaker+version+wwf&pg=PT104|url-status=live}} He made his overall WWF debut on a November 19, 1990, taping of WWF Superstars quickly defeating his first opponent, Mario Mancini, in a singles match{{cite news|url=https://books.google.com/books?id=SJkOBAAAQBAJ&dq=debut+Kane+The+Undertaker+at+a+taping+of+Superstars+WWF&pg=PA101|title=The Complete WWF Video Guide Volume II - Page 101|access-date=February 12, 2022|work=Lulu Press Incorporated|last=Simonotti|first=Christine|date=November 25, 2012|isbn=9781291252927|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003417/https://books.google.com/books?id=SJkOBAAAQBAJ&dq=debut+Kane+The+Undertaker+at+a+taping+of+Superstars+WWF&pg=PA101|url-status=live}} (this match was filmed three days prior to the Undertaker's televised debut at Survivor Series on November 22, but did not air on television until December 15, 1990). Also prior to his Survivor Series appearance, Kane the Undertaker had a match on November 20 against Rick Sampson, which later aired on the December 9, 1990 episode of WWF Wrestling Challenge.{{cite news|url=https://bleacherreport.com/articles/1574817-undertaker-and-the-end-of-an-era-the-death-of-the-gimmick-in-wwe|title=Undertaker and the End of an Era: The Death of the Gimmick in WWE|access-date=February 15, 2022|work=Bleacher Report|last=Snowden|first=Jonathan|date=March 21, 2013|archive-date=February 15, 2022|archive-url=https://web.archive.org/web/20220215175044/https://bleacherreport.com/articles/1574817-undertaker-and-the-end-of-an-era-the-death-of-the-gimmick-in-wwe|url-status=live}}

Calaway's official televised debut was at Survivor Series in which he was presented as the heel mystery partner of Ted DiBiase's "Million Dollar Team".2007 Wrestling almanac & book of facts. "Wrestling's historical cards", p. 88–89. Approximately one minute into the match, the Undertaker eliminated Koko B. Ware with his finisher, the Tombstone Piledriver.{{cite news|url=https://prowrestlingstories.com/pro-wrestling-stories/undertaker-first-year-wwe/|title=The Undertaker – His Memorable First Year in WWE|access-date=February 26, 2022|work=Prowrestling Stories|last=Shank|first=Cameron|archive-date=February 26, 2022|archive-url=https://web.archive.org/web/20220226231602/https://prowrestlingstories.com/pro-wrestling-stories/undertaker-first-year-wwe/|url-status=live}} (In 2018, Koko B. Ware shared that directly following this match that night, he confronted the Undertaker with serious objections to what he felt was a botched Tombstone. Though Ware also shared that he always admired Mark Calaway and perceived him as a great performer).{{cite news|url=https://uproxx.com/prowrestling/undertaker-first-tombstone-piledriver-koko-b-ware/|title=The Undertaker's Very First Tombstone Piledriver Was A Botch Says The Poor Guy Who Took It|access-date=September 7, 2022|date=August 10, 2018|work=Prowrestling|last=Stroud|first=Brandon|archive-date=September 8, 2022|archive-url=https://web.archive.org/web/20220908000150/https://uproxx.com/prowrestling/undertaker-first-tombstone-piledriver-koko-b-ware/|url-status=live}} During the match, the Undertaker also eliminated Dusty Rhodes before being counted out; however, his team won the match with DiBiase being the sole survivor. During the match, Calaway was referred to as simply the Undertaker, omitting the portion "Kane", which was dropped shortly after the event (and seven years later at the urgings of Prichard, given to another wrestler once he took on the role of the Undertaker's younger brother). Throughout the end of 1990, the Undertaker mostly picked up squash victories against jobbers on Superstars of Wrestling and Wrestling Challenge tapings. He was a participant in the 1991 Royal Rumble match which was won by Hulk Hogan.

In February 1991, Brother Love delegated his short-lived management role of the Undertaker over to Paul Bearer (real-life funeral director), Love communicating the need for someone who better aligned with the Undertaker's "deadman" themes.{{cite news|url=https://bleacherreport.com/articles/1805669-full-career-retrospective-and-greatest-moments-for-paul-bearer|title=Full Career Retrospective and Greatest Moments for Paul Bearer|access-date=February 26, 2022|work=Bleacher Report|last=Beaston|first=Erik|date=October 10, 2013|archive-date=February 26, 2022|archive-url=https://web.archive.org/web/20220226222949/https://bleacherreport.com/articles/1805669-full-career-retrospective-and-greatest-moments-for-paul-bearer|url-status=live}} Histrionic, wailing and ghostly in character, Bearer complemented the Undertaker and was almost always seen bearing an urn which he raised in the air to transmit supernatural healing powers to the Undertaker; this typically resulted in the Undertaker recovering from attacks and counterattacking his adversaries. During his early years, the Undertaker took to a post-match ritual of placing his defeated opponents (almost always jobbers) in a body bag and carrying them backstage.{{cite web|url=http://prowrestling.about.com/od/thewrestlers/tp/scarywrestlers.htm|title=About.com: Top 10 Scariest Wrestlers|publisher=Prowrestling.about.com|date=September 24, 2010|access-date=October 24, 2011|archive-date=July 7, 2011|archive-url=https://web.archive.org/web/20110707075052/http://prowrestling.about.com/od/thewrestlers/tp/scarywrestlers.htm|url-status=dead}} He continued picking up victories in squash matches leading up to his first feud in the WWF with "Superfly" Jimmy Snuka.

The Undertaker made his WrestleMania debut at WrestleMania VII on March 24, 1991, quickly defeating "Superfly" Jimmy Snuka.{{cite web|url=http://www.wwe.com/superstars/smackdown/undertaker/wrestlemanialegacy/|title=WrestleMania Legacy|access-date=July 10, 2008|publisher=WWE|archive-date=April 13, 2016|archive-url=https://web.archive.org/web/20160413111249/http://www.wwe.com/superstars/smackdown/undertaker/wrestlemanialegacy/|url-status=live}} He began his first major feud shortly thereafter, which was with The Ultimate Warrior when The Undertaker attacked him and locked him in an airtight casket on the set of Paul Bearer's Funeral Parlor segment. Resulting from this, the Warrior enlisted the assistance of Jake "The Snake" Roberts to get him mentally psyched for The Undertaker's morbid alarmist tactics: Roberts would drill the Warrior with "know your enemy" training, setting up the Warrior in a series of creepy, terrorizing circumstances, such as by locking him in caskets and in rooms with snakes.{{cite news|url=https://www.yahoo.com/news/world-wrestling-eerietainment-ranking-wwes-171509026.html|title=World Wrestling Eerietainment: Ranking WWE's Worst-Ever 'Horror Movie' Moments|access-date=February 26, 2022|work=Yahoo!|last=Birch|first=Nathan|date=July 15, 2016|archive-date=February 27, 2022|archive-url=https://web.archive.org/web/20220227002140/https://www.yahoo.com/news/world-wrestling-eerietainment-ranking-wwes-171509026.html|url-status=dead}} This culminated in a final stage of Roberts's training in which Roberts proved to be stringing Warrior along the entire time by assisting The Undertaker in an ambush. The Undertaker would later suffer his first losses in the WWF to The Ultimate Warrior, including in a first ever body bag challenge, a casket match, and (at house show) standard pin-fall match.{{cite news|url=https://www.sportscasting.com/the-undertaker-was-asked-ridiculously-hilarious-question-by-the-ultimate-warrior-early-wwe-matches/|title=The Undertaker Was Asked a Ridiculously Hilarious Question by The Ultimate Warrior During One of His Early WWE Matches|access-date=February 26, 2022|work=Sportscasting|last=Norris|first=Luke|date=February 21, 2021|archive-date=February 27, 2022|archive-url=https://web.archive.org/web/20220227003332/https://www.sportscasting.com/the-undertaker-was-asked-ridiculously-hilarious-question-by-the-ultimate-warrior-early-wwe-matches/|url-status=live}} The feud was, however, cut short after the Warrior's suspension and ongoing issues with Vince McMahon. In the 1991 King of the Ring, Undertaker defeated Animal in a qualifying match before fighting Sid Vicious to a double disqualification in the semifinal, which saw both men eliminated from the King of the Ring tournament.{{cite news|url=https://www.wrestlingdata.com/index.php?befehl=bios&wrestler=27&bild=2&details=7&liga=3&jahr=1991&seite=9|title=The Undertaker|access-date=February 26, 2022|work=Wrestlingdata.com|archive-date=February 27, 2022|archive-url=https://web.archive.org/web/20220227014641/https://www.wrestlingdata.com/index.php?befehl=bios&wrestler=27&bild=2&details=7&liga=3&jahr=1991&seite=9|url-status=live}}

The Undertaker defeated Hulk Hogan to win his first WWF Championship at Survivor Series with the help of Ric Flair and thus became the youngest WWF Champion in history to that point, 26 years of age—this record was later broken by Yokozuna in April 1993 at WrestleMania IX.PWI Staff. 2007 Wrestling almanac & book of facts. "Wrestling's historical cards", p. 89–90. The Undertaker's Tombstone of Hogan to win the WWF Championship at the 1991 Survivor Series created real-life, offscreen discord between the two, which Undertaker attributes his short title reign, lack of title runs during his early career and distrust of Hogan.{{cite web|url=https://www.espn.com/wwe/story/_/id/29242242/undertaker-first-wwe-title-win-hulk-hogan-memories-montreal-screwjob|title=Undertaker on first WWE title win against Hulk Hogan, memories of Montreal Screwjob|last=Shoemaker|first=David|date=May 31, 2020|publisher=ESPN|access-date=January 24, 2022|archive-date=January 29, 2022|archive-url=https://web.archive.org/web/20220129214852/https://www.espn.com/wwe/story/_/id/29242242/undertaker-first-wwe-title-win-hulk-hogan-memories-montreal-screwjob|url-status=live}} In storyline, however, WWF President Jack Tunney ordered a rematch between the two at This Tuesday in Texas six days later, where The Undertaker lost the title back to Hogan. However, due to the controversial endings of the two title matches between The Undertaker and Hogan, the title was vacated from Hogan the next night by Tunney. The company was without a WWF Champion until Ric Flair earned it by winning the 1992 Royal Rumble match.{{cite news|url=https://bleacherreport.com/articles/2595346-wwe-throwback-thursday-the-undertaker-vs-hulk-hogan-at-this-tuesday-in-texas|title=WWE Throwback Thursday: The Undertaker vs. Hulk Hogan at This Tuesday in Texas|access-date=February 26, 2022|work=Bleacher Report|last=Mueller|first=(The Doctor) Chris|date=December 3, 2015|archive-date=February 27, 2022|archive-url=https://web.archive.org/web/20220227015308/https://bleacherreport.com/articles/2595346-wwe-throwback-thursday-the-undertaker-vs-hulk-hogan-at-this-tuesday-in-texas|url-status=live}}

In February 1992, The Undertaker's ally Jake "The Snake" Roberts tried to attack "Macho Man" Randy Savage's manager/wife Miss Elizabeth with a steel chair when Undertaker stopped him, turning him (and Paul Bearer) face for the first time. Their face turn was solidified on the February 29 episode of Superstars when Roberts confronted The Undertaker on the Funeral Parlor set over the matter (aired on Saturday Night's Main Event XXX). After demanding to know whose side The Undertaker was on and getting the reply, "Not yours", Roberts attacked both Bearer and The Undertaker, only for The Undertaker to stand his ground and run Roberts off. The Undertaker defeated Roberts at WrestleMania VIII. He then feuded extensively with wrestlers managed by Harvey Wippleman throughout 1992 and 1993, such as Kamala and Giant González. Also during this time, The Undertaker headlined the debut episode of Monday Night Raw on January 11, 1993, with a victory over Damien Demento.{{cite news|url=https://www.youtube.com/watch?v=u4CPAS4HyaQ|title=The Undertaker wins the main event of the first Raw: Raw, Jan. 11, 1993|access-date=February 10, 2022|work=WWE|date=January 11, 1993|archive-date=February 10, 2022|archive-url=https://web.archive.org/web/20220210072151/https://www.youtube.com/watch?v=u4CPAS4HyaQ&gl=US&hl=en|url-status=live}}{{cite news|url=https://books.google.com/books?id=zbwxAwAAQBAJ&dq=Damien+Demento+Undertaker+RAW&pg=PA86|title=WWE 50 (p. 86)|access-date=February 10, 2022|work=DK|last=Sullivan|first=Kevin|date=January 1, 2014|isbn=9781465427762|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003415/https://books.google.com/books?id=zbwxAwAAQBAJ&dq=Damien+Demento+Undertaker+RAW&pg=PA86|url-status=live}} According to Calaway, working with González "...{{nbsp}}was survival every night trying to figure out what he could do" and "took years off my career".{{cite web| url-status = bot: unknown| archive-url = https://web.archive.org/web/20200810151918/https://www.youtube.com/watch?v=fYjd7StlJHs&feature=emb_title| archive-date = August 10, 2020| url = https://www.youtube.com/watch?v=fYjd7StlJHs&feature=emb_title| title = The Undertaker FULL INTERVIEW {{!}} Jim Norton & Sam Roberts| website = YouTube| date=June 17, 2020 | access-date = June 25, 2020}} He faced González at WrestleMania IX, which is notable as The Undertaker's only disqualification win at WrestleMania after the use of chloroform.{{cite news|url=https://bleacherreport.com/articles/1063656-wwe-opinion-what-the-wwe-can-learn-from-the-undertakers-wrestlemania-streak|title=WWE Opinion: What the WWE Can Learn from the Undertaker's WrestleMania Streak|access-date=February 22, 2022|work=Bleacher Report|last=Konuwa|first=Alfred|date=February 12, 2012|archive-date=February 22, 2022|archive-url=https://web.archive.org/web/20220222070735/https://bleacherreport.com/articles/1063656-wwe-opinion-what-the-wwe-can-learn-from-the-undertakers-wrestlemania-streak|url-status=live}} The Undertaker's next rivalry initiated at Survivor Series with Yokozuna when a clash between the two lost control, causing them to be counted out in an elimination tag match.{{cite news|url=https://www.youtube.com/watch?v=cRpxhRuE_so|title=The All-Americans defend their country's honor against The Foreign Fanatics: Survivor Series 1993|access-date=February 22, 2022|work=WWE|date=November 6, 2012|archive-date=February 22, 2022|archive-url=https://web.archive.org/web/20220222105618/https://www.youtube.com/watch?v=cRpxhRuE_so|url-status=live}} In the weeks following, The Undertaker and Bearer spooked Yokozuna with multiple segments from their wintery and remote rural area workshop. There, Bearer presented The Undertaker hard at work carpentering Yokozuna what would eventually become a "double wide, double deep casket" custom-built for Yokozuna's immensely overweight size.{{cite news|url=https://bleacherreport.com/articles/477785-wwe-legend-the-undertaker-the-phenom-over-rated-really|title=WWE Legend The Undertaker: Is the Phenom Overrated...Really?|access-date=February 22, 2022|work=Bleacher Report|last=Power|first=Dan|date=September 29, 2010|archive-date=February 22, 2022|archive-url=https://web.archive.org/web/20220222093831/https://bleacherreport.com/articles/477785-wwe-legend-the-undertaker-the-phenom-over-rated-really|url-status=live}} The feud culminated in a WWF Championship casket match at the Royal Rumble in January 1994. During the match, Yokozuna sealed The Undertaker in the casket with the assistance of a multitude of heel wrestlers (some of them Whippleman-managed) hired by Yokozuna's vindictive managers Jim Cornette and Mr. Fuji, which was in retaliation for Bearer's casket match stipulation that he snuck into their Royal Rumble match contract. After being trapped inside the casket by the pack, green vapor emitted from the casket and the arena lights went out. Undertaker then appeared from inside the casket on the video screen, representing the spirit of his dead corpse, warning that he would produce a future "rebirth" of himself, explaining to his antagonists that he cannot and will not Rest in Peace.PWI Staff. 2007 Wrestling almanac & book of facts. "Wrestling's historical cards", p. 92–94. The Undertaker did not appear in the WWF for seven months after his loss to Yokozuna. In reality, he was given time off to allow a back injury to heal, and to attend his first son's birth.{{cite web|url=http://grantland.com/features/wwe-summerslam-john-cena-brock-lesnar-pay-per-view/|title=What's at Stake When John Cena Wrestles Brock Lesnar at 'SummerSlam'|last=Shoemaker|first=David|date=August 14, 2014|publisher=Grantland|access-date=February 23, 2015|archive-date=April 20, 2016|archive-url=https://web.archive.org/web/20160420232912/http://grantland.com/features/wwe-summerslam-john-cena-brock-lesnar-pay-per-view/|url-status=live}}{{Cite book |last=Hart |first=Bret |title=HITMAN: My Real Life In The Cartoon World Of Wrestling |publisher=Grand Central Publishing |year=2009 |isbn=9780446546072 |pages=44}}

File:Paul Bearer in 1996.jpg betrayed The Undertaker by hitting him with the urn that he is seen carrying.]]

Following the death angle at the Royal Rumble during The Undertaker's absence, the WWF promoted reported sightings of him through video clips of random people claiming to have seen him. After WrestleMania X, Ted DiBiase introduced an Undertaker back to the WWF. This Undertaker, however, played by Brian Lee (one of Calaway's real-life best friends){{cite news|url=https://www.youtube.com/watch?v=Cj5shSINnsw|title=Paul Bearer on managing Undertaker vs Hogan, Giant Gonzales, Jake Roberts & more|work=RfVideoVault|access-date=March 9, 2022|archive-date=March 9, 2022|archive-url=https://web.archive.org/web/20220309124832/https://www.youtube.com/watch?v=Cj5shSINnsw&gl=US&hl=en|url-status=live}} was an impostor Undertaker (dubbed "The Underfaker" by fans){{cite news|url=https://books.google.com/books?id=nGQgdVxpuQ4C&dq=undertaker+wwf+summerslam+1994&pg=PA20|title=WWE Undertaker (p. 20)|access-date=February 12, 2022|work=DK|last=Sullivan|first=Kevin|date=November 2, 2009|isbn=9780756676438|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003414/https://books.google.com/books?id=nGQgdVxpuQ4C&dq=undertaker+wwf+summerslam+1994&pg=PA20|url-status=live}} rejuvenated by Dibiase's money rather than Bearer's urn. His actions led to the return of the real Undertaker at SummerSlam, defeating the impostor and appearing as a reincarnation of his Deadman gimmick, one of a more shadowy, mysterious and secret presence.{{cite news|url=https://bleacherreport.com/articles/2585210-undertaker-25-defining-moments-for-25-years-in-wwe|title=Undertaker: 25 Defining Moments for 25 Years in WWE (section 15 of 25)|access-date=February 12, 2022|work=Bleacher Report|last=Beaston|first=Erik|date=November 2, 2015|archive-date=February 13, 2022|archive-url=https://web.archive.org/web/20220213004406/https://bleacherreport.com/articles/2585210-undertaker-25-defining-moments-for-25-years-in-wwe|url-status=live}} Represented now by cool colors, The Undertaker replaced details of his wrestling gear that were previously colored gray with purple, and effected scenes with blue/purple semidarkness. Many details that would become associated with The Undertaker for the remainder of his career were produced during this rebirth incarnation, such as the addition of sleeve tattoos and Godlike supernatural elements (thunder, lightning and windy weather-like effects used to indicate The Undertaker's presence and wrath).{{cite news |url=https://www.espn.com/wwe/story/_/id/17328615/ten-wwe-summerslam-moments-memories-define-history-event|title=Best moments and memories of SummerSlam|access-date=February 12, 2022|work=ESPN|date=August 19, 2020}}{{cite news|url=https://bleacherreport.com/articles/2585210-undertaker-25-defining-moments-for-25-years-in-wwe|title=Undertaker: 25 Defining Moments for 25 Years in WWE|access-date=February 20, 2022|work=Bleacher Report|last=Beaston|first=Erik|date=November 2, 2015|archive-date=February 13, 2022|archive-url=https://web.archive.org/web/20220213080426/https://bleacherreport.com/articles/2585210-undertaker-25-defining-moments-for-25-years-in-wwe|url-status=live}}

Seeking retribution, The Undertaker revisited his feud with Yokozuna and eventually faced him in a casket rematch at Survivor Series. Chuck Norris (portraying his Walker, Texas Ranger persona) was involved in the match as special guest enforcer, preventing interference from wrestlers that Yokozuna, Jim Cornette and Mr. Fuji had again enlisted for help.{{cite news|url=https://books.google.com/books?id=E-bEDwAAQBAJ&dq=chuck+norris+the+undertaker+survivor+series+yokozuna&pg=PA113|title=WWE Beyond Extreme - Page 113|access-date=February 22, 2022|work=DK|last=Miller|first=Dean|date=March 17, 2020|isbn=9780744024197|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003422/https://books.google.com/books?id=E-bEDwAAQBAJ&dq=chuck+norris+the+undertaker+survivor+series+yokozuna&pg=PA113|url-status=live}} Unable to rely on much as far as interference this time around (only Irwin R. Schyster able to get in a brief ambush) due to Norris averting the attempts of several heel wrestlers, Yokozuna was defeated by The Undertaker and sealed in the casket. Throughout most of 1995, Undertaker feuded with members of Ted DiBiase's Million Dollar Corporation. The chain of wrestlers DiBiase enlisted to do away with The Undertaker started with Irwin R. Schyster at the Royal Rumble for which The Undertaker was victorious, but assaulted by another member of the Million Dollar Team, King Kong Bundy. While being assaulted, Bearer was deprived of his urn by the Corporation.{{cite news|url=https://bleacherreport.com/articles/605887-wwes-looking-back-at-legends-best-feuds-of-the-biggest-stars-in-ppv-era-ep-3|title=WWE's Looking Back At Legends: Best Feuds Of the Biggest Stars in PPV Era, Ep. 3|access-date=February 22, 2022|work=Bleacher Report|last=Hubbs|first=Joe|date=February 11, 2011|archive-date=February 22, 2022|archive-url=https://web.archive.org/web/20220222124606/https://bleacherreport.com/articles/605887-wwes-looking-back-at-legends-best-feuds-of-the-biggest-stars-in-ppv-era-ep-3|url-status=live}} At WrestleMania XI, The Undertaker made short work of Bundy in a singles match. This edition of WrestleMania included the first mention of The Undertaker's historic WrestleMania-winning Streak, acknowledged on commentary by Vince McMahon as Undertaker made his entrance: "The Undertaker, on his way to the ring—a man who's never lost at WrestleMania."{{cite news|url=https://www.theringer.com/2018/4/4/17195692/undertaker-career-wrestlemania-wwe-wrestling-streak|title=Dead Man Rising: On the eve of his 26th 'WrestleMania,' we talked to friends, colleagues, and victims of the WWE's longest-reigning superstar about the making of the amazing career and (after)life of the Undertaker|access-date=February 22, 2022|work=The Ringer|last=Golianopoulos|first=Thomas|date=April 4, 2018|archive-date=February 22, 2022|archive-url=https://web.archive.org/web/20220222122010/https://www.theringer.com/2018/4/4/17195692/undertaker-career-wrestlemania-wwe-wrestling-streak|url-status=live}} During The Undertaker's WrestleMania encounter, DiBiase issued him with yet another antagonist in "The Supreme Fighting Machine" Kama, who had stolen the briefly recaptured urn from Bearer during the match. Kama followed this up with a series of malicious acts, including destroying the stolen urn and recycling it into bling.{{cite news|url=https://books.google.com/books?id=7-JpBQAAQBAJ&dq=kama+turns+the+urn+into+bling+undertaker&pg=PA98|title=The Complete WWF Video Guide Volume III - Page 98|access-date=February 22, 2022|work=Lulu.com|last=Dixon|first=James|date=May 7, 2013|isbn=9781291411072|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003414/https://books.google.com/books?id=7-JpBQAAQBAJ&dq=kama+turns+the+urn+into+bling+undertaker&pg=PA98|url-status=live}} While sporting the flashy bling around his neck, he repeatedly cost The Undertaker matches and attacked diehard Undertaker fans, dubbed "Creatures of the Night". In August, Undertaker settled the score with Kama, defeating him in a casket match at SummerSlam. Several weeks later, Undertaker suffered a serious orbital bone injury when King Mabel unintentionally struck him in the eye with his fist during a house show, forcing The Undertaker into a period of absence for surgery. Due to the incident happening at a house show, Vince McMahon had it presented to the audience as though it had occurred from Mabel and Yokozuna's exchange of leg drops and splashes on The Undertaker on the Monday Night Raw that had aired 2 days prior.{{cite news|url=https://books.google.com/books?id=mxxPBwAAQBAJ&dq=undertaker+injured+his+orbital+bone+1995&pg=PA165|title=Titan Sinking: The decline of the WWF in 1995 - Page 165|access-date=February 22, 2022|work=Lulu.com|last1=Dixon|first1=James|last2=Cornette|first2=Jim|last3=Richardson|first3=Benjamin|date=August 2, 2014|isbn=9781291996371|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003415/https://books.google.com/books?id=mxxPBwAAQBAJ&dq=undertaker%20injured%20his%20orbital%20bone%201995&pg=PA165|url-status=live}} The Undertaker returned a couple months later at Survivor Series, in which he single-handedly eliminated an entire team of wrestlers led by King Mabel, The Undertaker leading his own team to victory.{{cite news|url=https://books.google.com/books?id=TM38w278TJIC&dq=undertaker+destroys+mabel%27s+team+at+survivor+series&pg=PA14|title=Master of Pain|access-date=February 23, 2022|work=Rosen Publishing|last=Bringle|first=Jennifer|date=December 15, 2011|isbn=9781448855360|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003425/https://books.google.com/books?id=TM38w278TJIC&dq=undertaker+destroys+mabel%27s+team+at+survivor+series&pg=PA14|url-status=live}} It was at that Survivor Series return in which he began wearing a Phantom of the Opera-like, gray upper-face mask to safeguard his orbital injury while it healed. The following month in December, The Undertaker defeated Mabel in a casket match at In Your House, retrieving the urn, which had been traded between several of The Undertaker's antagonists over the course of the year.

In the main event of the Royal Rumble in January 1996, The Undertaker was unmasked of his Phantom of the Opera-like facial covering in a WWF Championship match against Bret Hart. The Undertaker was eventually able to hit the Tombstone Piledriver on Hart, but Diesel interfered, costing The Undertaker the championship.2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.95) A rematch for the title on the February 5 episode of Raw saw similar interference.{{cite news|url=https://insidepulse.com/2011/02/16/what-the-world-was-watching-wwf-monday-night-raw-february-5-1996/|title=What the World Was Watching: WWF Monday Night Raw – February 5, 1996|access-date=February 9, 2022|work=Inside Pulse|last=Scisco|first=Logan|date=February 16, 2011|archive-date=February 9, 2022|archive-url=https://web.archive.org/web/20220209193246/https://insidepulse.com/2011/02/16/what-the-world-was-watching-wwf-monday-night-raw-february-5-1996/|url-status=live}} At that month's In Your House: Rage in the Cage, while Diesel was facing Hart in a steel cage match for the WWF Championship, The Undertaker delivered a surprise attack, emerging from a hole he had ripped through the ring canvas and dragging Diesel with him down under amid a cloud of smoke, allowing Hart the victory. After several weeks of more retaliatory one-upmanship between Diesel and The Undertaker, their feud culminated in a singles match at WrestleMania XII, where Undertaker was victorious.

The Undertaker's next feud commenced the next night on Raw when Mankind, a twisted and tortured soul, made his debut and randomly interfered in Undertaker's match against Justin "Hawk" Bradshaw. For the next few months, Mankind viciously ambushed The Undertaker and cost him multiple matches. Among them, Mankind cost The Undertaker the WWF Intercontinental Championship by interfering in his casket match against Goldust at In Your House 8: Beware of Dog. In interfering in this match, Mankind proved to have mystifying horror tactic capabilities that matched The Undertaker's, mysteriously appearing from inside the casket and sealing The Undertaker inside. The Undertaker, however, had vanished amid a cloud of smoke once the casket lid was opened.{{cite news|url=https://bleacherreport.com/articles/542052-cvc-undertaker-versus-mankind-the-best-and-most-bizarre-rivalry-ever|title=CvC: Undertaker vs. Mankind, The Best and Most Bizarre Rivalry Ever|access-date=February 23, 2022|work=Bleacher Report|last=M|first=Buzz|date=December 15, 2010|archive-date=February 23, 2022|archive-url=https://web.archive.org/web/20220223071828/https://bleacherreport.com/articles/542052-cvc-undertaker-versus-mankind-the-best-and-most-bizarre-rivalry-ever|url-status=live}} As a result of the interference and repeated ambushes from Mankind on The Undertaker throughout the ensuing weeks, The Undertaker and Mankind competed in their first on-screen bout at the 1996 King of the Ring, a heated encounter in which The Undertaker presented as uncharacteristically intense. During the match, Bearer inadvertently hit The Undertaker with the urn, allowing Mankind to incapacitate The Undertaker with his finisher, the Mandible Claw, and score the win. With Mankind insatiably continuing to cost The Undertaker matches even following their King of the Ring encounter, The Undertaker began firing back with rage and the feud spiraled out of control: the two routinely interrupted other matches already in progress, battling each other at random intervals outside of having arranged matches—their chaos also spilling into audiences, arena backstage communal areas, and arena boiler rooms, all of this unprecedented at the time. As a result, the first ever Boiler Room Brawl (Mankind's specialty match) was booked between the two at SummerSlam. After more than 20 minutes of brawling with Mankind in the Cleveland Gund Arena's boiler room, the arena corridors, the SummerSlam entrance area and aisleway to the ring, The Undertaker reached for Paul Bearer's urn in an attempt to win the match, but Bearer struck him with it, betraying The Undertaker. This followed with Bearer allowing Mankind to take hold of the urn, thus winning this match. According to Paul Bearer in shoot interviews the WWF wanted Bearer to betray him during that match because it was a storyline that Kane was coming and they wanted The Undertaker to get ready for the angle with Kane the following year by having Bearer turn on him. After Bearer's betrayal, The Undertaker grew more aggressive, resolving his feud against Goldust (Mankind's comrade in tormenting The Undertaker) at In Your House 10: Mind Games. The Undertaker then took his rivalry with Mankind to new lengths in a specialty match of his own, and at that time unprecedented Buried Alive match to take place in the main event of In Your House 11: Buried Alive. The Undertaker won the match after chokeslamming Mankind into the open grave and subsequently shoveling enough dirt on him so that he was covered. However, after interference from the debuting Executioner, as well as the help of several other heel wrestlers apparently enlisted by Bearer, Mankind escaped the grave and together the mob all shoveled dirt onto The Undertaker to the point that the grave was completely filled, resulting in The Undertaker fully buried alive. Not without a parting message for the pack, however, The Undertaker's purple glove fit hand emerged from his burying place amid a bolt of lightning that had erupted over the gravesite. The scene sent all of his antagonists fleeing.

After being buried alive and a following month-long hiatus, The Undertaker returned at the Survivor Series again pitting him against Mankind, but with a unique stipulation: Hanging {{convert|20|ft|m|abbr=on|disp=flip}} above the ring would be Paul Bearer, enclosed in a steel cage. And if The Undertaker were to win the match, he would be rewarded the opportunity to assault Bearer however he pleased. Even though The Undertaker won this match, interference from The Executioner enabled Bearer to escape Undertaker's clutches.PWI Staff. 2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p. 96–97). It was also at this event that The Undertaker had developed a comparatively more humanized and more informal yet still superhuman "Deadman" incarnation. In this then new form, he took on a Goth appearance and persona, with a brash, rebelling, Championship-driven mean streak (perhaps to better fit in with the then-budding, more adult-oriented Attitude Era).{{cite news|url=https://www.essentiallysports.com/wwe-news-deadman-to-american-bada-transformation-of-the-undertakers-gimmick-and-attire-over-the-years-the-undertaker/|title=Deadman to American Bada**- Transformation of The Undertaker's Gimmick and Attire Over the Years|access-date=February 9, 2022|work=Essentially Sports|last=Mishra|first=Prithvi|date=October 28, 2021|archive-date=February 9, 2022|archive-url=https://web.archive.org/web/20220209200341/https://www.essentiallysports.com/wwe-news-deadman-to-american-bada-transformation-of-the-undertakers-gimmick-and-attire-over-the-years-the-undertaker/|url-status=live}} This delivering, dubbed "The Lord of Darkness", was the 3rd incarnation of his Deadman persona. Following Survivor Series, The Undertaker briefly turned his attention to The Executioner, who had been interfering in his matches since his arrival. At In Your House 12: It's Time, The Undertaker defeated The Executioner in an Armageddon Rules match even with Mankind heavily involved throughout the entire encounter. The Undertaker then moved on to feud with Vader, whom he faced in January 1997 at the Royal Rumble in a singles match, which The Undertaker lost after Bearer interfered on behalf of his new protégé. The two then clashed in the Royal Rumble match itself as they made it to the final moments of the match, but both were eliminated by Stone Cold Steve Austin, who had crept back into the match after his elimination was unseen. He faced both Vader and Austin in a four-corners elimination match for the vacant WWF Championship at In Your House 13: Final Four, but Bret Hart won.{{cite web|title=Final Four results|date=February 16, 1997|url=http://www.prowrestlinghistory.com/supercards/usa/wwf/miscppvs1990s.html#13|access-date=December 7, 2011|publisher=Wrestling Supercards and Tournaments|archive-date=April 12, 2008|archive-url=https://web.archive.org/web/20080412162128/http://prowrestlinghistory.com/supercards/usa/wwf/miscppvs1990s.html#13|url-status=live}} However, the following month, The Undertaker managed to win the WWF Championship for the second time by defeating Sycho Sid at WrestleMania 13.2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p. 98–99). Reviving his first Deadman incarnation for that night only, The Undertaker appeared as the "Old West Mortician", donning the trademarked gray wrestling gear accessories (boot spats, tie, gloves), along with a pitch-black entrance with only a white spotlight shined over him, contrasted from the purple/blue semidarkness associated with the rest of his Deadman incarnations.

Following his WWF Championship win at WrestleMania 13, Paul Bearer attempted to rejoin The Undertaker as his manager. After The Undertaker refused and attacked Bearer, Bearer had Mankind set a fireball to the Undertaker's face, leading up to a match at In Your House 14: Revenge of the 'Taker, for which The Undertaker was victorious.{{cite news|url=http://placetobenation.com/reliving-a-feud-2-the-undertaker-vs-mankind-1996-1998/|title='Reliving A Feud #2: The Undertaker vs. Mankind, 1996 – 1998|access-date=February 10, 2022|work=Place to be Nation|date=February 1, 2013|archive-date=February 10, 2022|archive-url=https://web.archive.org/web/20220210094312/http://placetobenation.com/reliving-a-feud-2-the-undertaker-vs-mankind-1996-1998/|url-status=live}} Evening the score at "Revenge of the 'Taker", The Undertaker set a fireball to Bearer's face directly following the match. Following the event, Bearer bandaged up from fire burns, likened The Undertaker's assault to a past incident he described as The Undertaker's "deepest, darkest secret". Through giving The Undertaker the ultimatum of revealing his deepest, darkest secret to the world, Bearer was able to reunite with him as manager and protégé. After only a few months of abrasive behaviors from Bearer, however, The Undertaker lost his patience and rejected Bearer as his manager. In retaliation, Bearer disclosed that The Undertaker had intentionally killed his family by burning down his parents' family funeral home for which they raised him and his younger brother.{{cite news|url=https://www.redriverhorror.com/2021/01/26/death-and-taxes-and-takers/|title=Death and Taxes, and 'Takers|access-date=January 31, 2022|work=Red River Horror|last=Feese|first=Steven|date=January 26, 2021|archive-date=March 31, 2022|archive-url=https://web.archive.org/web/20220331071632/https://www.redriverhorror.com/2021/01/26/death-and-taxes-and-takers/|url-status=live}} (Note that the younger brother, Kane, was not revealed to be The Undertaker's half-brother until the following year, April 1998, when Bearer disclosed to the world that he is Kane's father, The Undertaker's mother having had an affair with him. Bearer later verified this with DNA test results).{{cite news|url=https://classicwrestlingreview.com/2022/01/09/over-the-edge-in-your-house/|title=Over The Edge: In Your House|access-date=February 10, 2022|work=Classic Wrestling Review|date=January 9, 2022|archive-date=February 10, 2022|archive-url=https://web.archive.org/web/20220210101518/https://classicwrestlingreview.com/2022/01/09/over-the-edge-in-your-house/|url-status=live}} At this point in his career, The Undertaker denied the charges of committing the arson murder that killed his family; however, Bearer claimed to have proof in the form of The Undertaker's alive and well younger brother, Kane, who had survived though scarred and burned. Bearer raised Kane after the fire, having him institutionalized from the date of the fire into adulthood. Ever since the fire, Kane had been awaiting to exact vengeance on his older half-brother. In defense, Undertaker responded that Kane, a "pyromaniac", had been the one to set the fire and, as a result, could not have possibly even survived. (Note that it would not be until a year and a half later from this point, in latter 1998, in which The Undertaker would shamelessly confess to intentional acts of arson to the funeral home that killed his parents and scarred his brother).

File:Undertaker standing 1997.jpg

In spite of Bearer projecting himself as a constant source of mental distress to The Undertaker during his Championship title reign, The Undertaker managed to secure successful title defenses against Stone Cold Steve Austin (A Cold Day In Hell: In Your House),{{cite news|url=https://books.google.com/books?id=ReANEAAAQBAJ&dq=the+undertaker+vs.+stone+cold+steve+austin+In+your+house+cold+day+in+hell+1997&pg=PT117|title=Austin 3:16: 316 Facts and Stories about Stone Cold Steve Austin|access-date=February 19, 2022|work=ECW Press|last=McAvennie|first=Michael|date=March 30, 2021|isbn=9781773057231|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003420/https://books.google.com/books?id=ReANEAAAQBAJ&dq=the+undertaker+vs.+stone+cold+steve+austin+In+your+house+cold+day+in+hell+1997&pg=PT117|url-status=live}} Faarooq (King of the Ring){{cite news|url=https://books.google.com/books?id=VUaPBgAAQBAJ&dq=The+undertaker+vs+Faarooq+1997+King+of+the+Ring&pg=PA58|title=The RAW Files|access-date=February 19, 2022|work=Lulu.com|last1=Dixon|first1=Dixon|last2=Furious|first2=Arnold|last3=Maughan|first3=Lee|date=February 1, 2014|isbn=9781291757798|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003413/https://books.google.com/books?id=VUaPBgAAQBAJ&dq=The+undertaker+vs+Faarooq+1997+King+of+the+Ring&pg=PA58|url-status=live}} and Vader (Canadian Stampede: In Your House, revisiting and settling their Royal Rumble feud from earlier on in the year),{{cite news|url=https://books.google.com/books?id=uDxbDgAAQBAJ&dq=the+undertaker+canadian+stampede+vader+1997&pg=PA139|title=The WWE Book of Top 10s|access-date=February 19, 2022|work=DK|last=Miller|first=Dean|date=May 9, 2017|isbn=9781465467171 }} respectively. Concurrent to the "deep, dark secret" storyline directed by Bearer, Undertaker began a then new rivalry at SummerSlam when special guest referee Shawn Michaels accidentally hit him with a steel chair shot intended for his archnemesis Bret Hart, in effect, costing The Undertaker the WWF Championship. The accidental chair shot led to Michaels feeling betrayed by the now booing WWF fans, and quickly becoming heel. Thus, a severely violent storyline with The Undertaker followed, one revolving around repeated intentional chair shots by Michaels on the Undertaker, Michaels taunting The Undertaker throughout.{{cite news|url=https://books.google.com/books?id=VUaPBgAAQBAJ&dq=shawn+michaels+hitting+undertaker+with+chair+1997+raw&pg=PA87|title=The RAW Files|access-date=February 19, 2022|work=Lulu.com|last1=Dixon|first1=Dixon|last2=Furious|first2=Arnold|last3=Maughan|first3=Lee|date=February 1, 2014|isbn=9781291757798|archive-date=February 12, 2024|archive-url=https://web.archive.org/web/20240212181043/https://books.google.com/books?id=VUaPBgAAQBAJ&dq=shawn+michaels+hitting+undertaker+with+chair+1997+raw&pg=PA87#v=onepage&q=shawn%20michaels%20hitting%20undertaker%20with%20chair%201997%20raw&f=false|url-status=live}} After the duo's first match, which was a chaotic and uncontrolled encounter that resulted in a double count-out draw at Ground Zero: In Your House, Undertaker challenged Michaels to the first ever Hell in a Cell match to take place at Badd Blood: In Your House. Despite the inclusion of the cell for more order and to prevent Michaels from receiving help from his D-Generation X stable, the encounter ended up even more uncontrolled and savage than their first and is considered one of The Undertaker's best matches of his career.{{cite news|url=https://books.google.com/books?id=jDtaAAAAYAAJ&q=Undertaker%27s+best+matches|title=Wrestling Observer Newsletter - Page 16|access-date=February 20, 2022|work=Wrestling Observer Newsletter|last=Meltzer|first=Dave|date=July 1, 2004|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003426/https://books.google.com/books?id=jDtaAAAAYAAJ&q=Undertaker%27s+best+matches|url-status=live}} Seemingly about to emerge the victor after striking Michaels with a chair shot of his own, The Undertaker was interrupted by his storyline half-brother Kane, finally making his debut. Under the control of Paul Bearer, Kane stormed the arena, ripped off the cell door, and laid out a nonplussed Undertaker with his own trademarked finisher, The Tombstone Piledriver, allowing Michaels to pin him for the victory. As the storyline progressed through Bearer having Kane mow down much of the WWF roster, Kane repeatedly challenged The Undertaker, going to lengths of tormenting and humiliating him. However, The Undertaker consistently refused to fight his half-brother, claiming he had made a vow to his parents never to do harm to his own "flesh and blood".{{cite news|url=https://books.google.com/books?id=YLXmDwAAQBAJ&dq=Undertaker+refuses+to+fight+kane+his+own+flesh+and+blood&pg=PT168|title=WWE Encyclopedia of Sports Entertainment New Edition|access-date=February 19, 2022|work=DK|date=September 29, 2020|isbn=978-0-7440-3510-0 |archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003428/https://books.google.com/books?id=YLXmDwAAQBAJ&dq=Undertaker+refuses+to+fight+kane+his+own+flesh+and+blood&pg=PT168|url-status=live |author1=D. K. }} The Undertaker's final encounter with Michaels during this chapter of his career was in a casket match for the WWF Championship at the Royal Rumble. The week before on Raw, Kane had duplicitously presented as allying with his brother against Michaels's D-Generation X stable; however, at the Royal Rumble, Kane trapped The Undertaker in the coffin, padlocked the lid shut, and set the casket ablaze, allowing Michaels another victory.PWI Staff. 2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p. 100–101). After a two-month hiatus in which Kane wreaked havoc over the WWF, The Undertaker returned on the March 2, 1998 episode of Raw in a most notable resurrection—his druids interrupting Kane and Bearer by presenting them with a coffin on the entrance stage amid a large number of bell tolls. The coffin was struck and dismantled by a lightning bolt, revealing a lied out Undertaker who sat up in a fury state and challenged Kane to do battle with him.{{cite news|url=https://bleacherreport.com/articles/1056114-wwe-ranking-the-undertakers-various-returns-to-the-ring|title=WWE: Ranking The Undertaker's Various Returns to the Ring|access-date=February 19, 2022|work=Bleacher Report|last=Massey|first=Daniel|date=February 6, 2012|archive-date=February 20, 2022|archive-url=https://web.archive.org/web/20220220045422/https://bleacherreport.com/articles/1056114-wwe-ranking-the-undertakers-various-returns-to-the-ring|url-status=live}} At WrestleMania XIV in their first match, The Undertaker defeated Kane. Kane challenged Undertaker to a rematch—Kane's specialty and first ever Inferno match—that occurred one month later at Unforgiven: In Your House. The Undertaker won the encounter by setting Kane's right arm on fire.

The Undertaker and Mankind's wildly violent, outlandish feud from over a year previous to this point was revitalized over the next month, ultimately taken to a new graphic height and decisively resolved when they faced each other in a Hell in a Cell match at King of the Ring. The match became one of the most famous matches in professional wrestling history. During the match, the Undertaker threw Mankind off the roof of the {{convert|16|ft|m|abbr=on|disp=flip}} cell onto a broadcast table below, in what was a preplanned move. He later performed a chokeslam on Mankind through the roof of the cell into the ring, which was not preplanned and legitimately knocked Mankind unconscious. In jumping from the top of the cell to the ring canvas, The Undertaker suffered a broken ankle. Escalating as things progressed, blood flowed from both wrestlers as they attacked each other with steel steps, chairs, the cell wall, etc. Topping that off, Mankind introduced multitudes of thumbtacks scattered across the ring canvas but was back body dropped on them, and subsequently chokeslammed onto them before The Undertaker won the match with his Tombstone Piledriver. At Fully Loaded: In Your House, the Undertaker and Stone Cold Steve Austin defeated Kane and Mankind to win the WWF Tag Team Championship. The Undertaker and Austin's reign as tag team champions lasted only two weeks, as Kane and Mankind regained the titles from them in a fatal four-way tag-team match on the August 10 episode of Raw is War.{{cite news|url=https://bleacherreport.com/articles/1074412-abandoned-the-history-of-wwes-world-tag-team-championship-pt-3|title=Abandoned: The History of WWE's World Tag Team Championship, Pt. 3 (See section 11 of 53)|access-date=February 10, 2022|work=Bleacher Report|last=Schadler|first=Kyle|date=February 21, 2012|archive-date=February 10, 2022|archive-url=https://web.archive.org/web/20220210075218/https://bleacherreport.com/articles/1074412-abandoned-the-history-of-wwes-world-tag-team-championship-pt-3|url-status=live}}{{cite news|url=https://insidepulse.com/2012/11/12/match-listing-and-artwork-for-wwes-the-attitude-era-dvd-blu-ray/|title=Match Listing And Artwork For WWE's The Attitude Era DVD & Blu-ray|access-date=February 10, 2022|work=Inside Pulse|last=Leamons|first=Travis|date=November 12, 2012|archive-date=February 10, 2022|archive-url=https://web.archive.org/web/20220210075219/https://insidepulse.com/2012/11/12/match-listing-and-artwork-for-wwes-the-attitude-era-dvd-blu-ray/|url-status=live}} The Undertaker then became the number one contender for the WWF Championship, held by Austin at that point, for a match at SummerSlam. Shortly before SummerSlam and after much speculation, The Undertaker finally disclosed that he and his half-brother were working together. Despite this revelation, The Undertaker told Kane before his SummerSlam bout that he did not want him interfering, even sending Kane away during the match itself when he appeared. Even though The Undertaker lost the match at SummerSlam, he handed Austin his championship belt back after the match with a show of respect and sportsmanship.

In September as the storyline matured however, The Undertaker subtly began showing some heel characteristics, becoming a tweener. This began when he and Kane revealed the fact that they were in cahoots to rid Austin of his title for villainous company owner Mr. McMahon—Austin and McMahon immersed in a bitter rivalry during this era. At Breakdown: In Your House, The Undertaker and Kane were booked in a triple threat match with Austin for the WWF Championship, in which McMahon stated that the brothers were not allowed to pin each other. The Undertaker and Kane pinned Austin simultaneously after a double chokeslam, ending the match in a no contest, so the title was vacated by McMahon. This event led to a match at Judgment Day: In Your House between The Undertaker and Kane for the title, with Austin as the special guest referee. Near the end of the match, Paul Bearer seemed about to assist Kane by handing him a steel chair to hit The Undertaker with, but as Kane had his back turned, both Bearer and The Undertaker hit Kane with chair shots. The Undertaker went for the pin, but Austin refused to count the fall, attacked The Undertaker and counted out both of them. Finally the next night on Raw is War, The Undertaker reconciled with Bearer and claimed that he and Bearer would unleash their "Ministry of Darkness" on the WWF, turning heel for the first time since 1992. As part of the then new storyline angle, The Undertaker admitted that he had indeed intentionally set the fire that killed his parents and scarred Kane, for which he had previously blamed on Kane.{{YouTube|uNCRvCc4XY0|"Undertaker admits to setting Kane on fire"}}

{{see also|Ministry of Darkness|Corporate Ministry}}

After Survivor Series, The Undertaker returned his attention to his previous feud with Austin for costing him the title at Judgment Day, hitting Austin in the head with a shovel during a title match with The Rock on the November 16 episode of Raw is War, returning the favor for what happened a month earlier. With this twist in the storyline, Mr. McMahon scheduled a Buried Alive match between The Undertaker and Austin at Rock Bottom: In Your House. In the weeks leading up to Rock Bottom, The Undertaker attempted to embalm Austin alive, tried to have Kane committed to a mental asylum, and had his druids chain Austin to an immense structure of his Undertaker crucifix-like logo (which took the appearance of a capital T combined X) before having that structure lifted up on high into the air.{{cite news|url=https://www.essentiallysports.com/wwe-news-watch-when-wwe-legend-the-undertaker-crucified-cold-steve-austin-in-a-chilling-segment/|title=WATCH: When WWE Legend the Undertaker Crucified Cold Steve Austin in a Chilling Segment|access-date=February 10, 2022|work=EssentiallySports|last=Chaudhury|first=Shuvangi|date=February 7, 2021|archive-date=February 11, 2022|archive-url=https://web.archive.org/web/20220211041225/https://www.essentiallysports.com/wwe-news-watch-when-wwe-legend-the-undertaker-crucified-cold-steve-austin-in-a-chilling-segment/|url-status=live}}{{cite news|url=https://www.youtube.com/watch?v=pm9yNgZ91TU|title=Undertaker attempts to embalm Stone Cold Steve Austin: This Week in WWE History, Dec. 8, 2016|access-date=February 10, 2022|work=WWE YouTube|date=December 8, 2016|archive-date=February 11, 2022|archive-url=https://web.archive.org/web/20220211041224/https://www.youtube.com/watch?v=pm9yNgZ91TU|url-status=live}} However, The Undertaker lost the Buried Alive match to Austin at Rock Bottom after Kane interfered.2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p. 102).

After the buildup to his second heel run in the latter part of 1998, The Undertaker introduced an updated version of his Deadman identity by January 1999—a dark priest-like character who in the initial period of this persona reigned over a stable known as The Ministry of Darkness. In this form, he took on a wicked, demonic presence, much more so than ever before. He often proclaimed to be invoking and taking orders from a "Higher Power". Moreover, he often appeared in a hooded black robe and sat on a throne with a towering backrest specially designed into his crucifix-like logo. With the help of his minions, he often performed sacrifices on select WWF wrestlers, using various incantations and magic words with intent to extract out the dark side of the wrestlers in question to recruit them into his Ministry. The completed Ministry of Darkness consisted of The Brood (Christian, Edge and Gangrel), The Acolytes (Bradshaw and Faarooq), Mideon and Viscera. Calaway himself did not wrestle for a period, having undergone a hip replacement. As part of the angle, The Undertaker had his Ministry members fight his battles, carry out his evil wishes and do all his dirty deeds. In this manner, he expressed his desires to take over the World Wrestling Federation, displacing its owner, Mr. McMahon. These ambitions culminated into a rivalry between The Ministry and The Corporation, ultimately resulting in a match between The Undertaker and Corporation enforcer, Big Boss Man. The two faced off in a Hell in a Cell match at WrestleMania XV, which The Undertaker won.{{cite web|url=http://www.wwe.com/shows/wrestlemania/history/wm15/results/|title=WrestleMania XV Results|publisher=WWE|access-date=March 21, 2013|archive-date=March 29, 2008|archive-url=https://web.archive.org/web/20080329175839/http://www.wwe.com/shows/wrestlemania/history/wm15/results/|url-status=live}} At Backlash: In Your House, The Undertaker defeated Corporation member Ken Shamrock after interference from Ministry member Bradshaw.{{cite web|url=http://www.pwwew.net/ppv/wwf/april/1999.htm|title=Backlash '99 Results|publisher=PWWEW.net|access-date=March 22, 2013|archive-date=February 25, 2020|archive-url=https://web.archive.org/web/20200225145109/http://www.pwwew.net/ppv/wwf/april/1999.htm|url-status=live}}

Thereafter, The Undertaker kidnapped Stephanie McMahon, forcing Mr. McMahon to enter into a reluctant alliance with his longtime nemesis Stone Cold Steve Austin. The Undertaker attempted to marry Stephanie before sacrificing her in an eldritch ceremony conducted by Paul Bearer, but Austin was able to rescue her.{{cite web|url= http://slam.canoe.ca/SlamWrestlingArchive/apr26_backlash.html|archive-url= https://archive.today/20120716183312/http://slam.canoe.ca/SlamWrestlingArchive/apr26_backlash.html|url-status= usurped|archive-date= July 16, 2012|title=Backlash: Austin wins, Stephanie abducted|date=April 26, 1999|work=Slam! Sports|publisher=Canadian Online Explorer|access-date=May 12, 2009}} At the Over the Edge pay-per-view, The Undertaker defeated Austin for his third WWF Championship with help from Shane McMahon, the special guest referee.2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.103) The Ministry eventually merged with Shane McMahon's Corporation alliance to form The Corporate Ministry. The Undertaker later revealed that Mr. McMahon had been his "Higher Power" all along as a scheme against Austin.Archived at [https://ghostarchive.org/varchive/youtube/20211212/tcXhMSOLJKM Ghostarchive]{{cbignore}} and the [https://web.archive.org/web/20140611221846/http://www.youtube.com/watch?v=tcXhMSOLJKM Wayback Machine]{{cbignore}}: {{cite web |title=The Higher Power of The Corporate Ministry is revealed |url=https://www.youtube.com/watch?v=tcXhMSOLJKM |website=YouTube | date=July 19, 2011 |publisher=WWE.com |access-date=January 10, 2020}}{{cbignore}} After The Undertaker lost the WWF Championship back to Austin on the Raw following King of the Ring and lost to him in a First Blood match at Fully Loaded, his relationship with the McMahons dissolved and The Corporate Ministry disbanded.{{cite news|url=https://www.cbr.com/higher-power-vince-undertaker-corporate-ministry/|title=The Higher Power: How Vince and Undertaker Formed the Corporate Ministry|access-date=February 10, 2022|work=Comic Book Resources|last=Rodriguez|first=Jesse|date=June 1, 2020|archive-date=February 10, 2022|archive-url=https://web.archive.org/web/20220210083440/https://www.cbr.com/higher-power-vince-undertaker-corporate-ministry/|url-status=live}}

The Undertaker then began a storyline where he teamed with Big Show in a tag team known as "The Unholy Alliance", which held the WWF Tag Team Championship twice. After their victory at SummerSlam, The Undertaker suffered a groin tear and was seen limping in several matches. He avoided competing in wrestling matches in the following weeks, instead overbearingly ordering Big Show to fight his battles and do all his dirty deeds. Developing a comedy horror smart mouth during this time, elements of The Undertaker's trash-talking biker identity (that he would eventually introduce in 2000) began peeping out during this phase of his career. According to an interview with Kevin Nash, this was a move to allow Calaway to return to WCW with a non-trademarked persona; had he entered WCW, it would have been as Mark Calaway. According to Nash, although negotiations were described as close, Calaway ultimately re-signed with the WWF. Conversely, while on Steve Austin's Broken Skull Sessions podcast on November 22, 2020, Calaway revealed that there was no way he was ever going to rejoin WCW, that the gimmick's biker transition was just a matter of him mixing things up because he didn't feel the character's Deadman side properly fit with the then ongoing Attitude Era.{{cite magazine |last=Barrasso |first=Justin |title=Pro wrestling's Wolfpac is tighter than ever |url=https://www.si.com/extra-mustard/2015/04/23/wwe-wcw-wolfpac-kevin-nash-scott-hall |access-date=October 30, 2020 |magazine=Sports Illustrated |date=April 23, 2015 |archive-date=May 13, 2021 |archive-url=https://web.archive.org/web/20210513031953/https://www.si.com/extra-mustard/2015/04/23/wwe-wcw-wolfpac-kevin-nash-scott-hall |url-status=live }}{{Cite web|url=http://411mania.com/wrestling/the-undertaker-wwe-wcw-character/|title=411MANIA|website=The Undertaker On Having Conversations With Kevin Nash About Jumping To WCW, When He Realized Potential Of His Character|access-date=November 26, 2020|archive-date=September 12, 2021|archive-url=https://web.archive.org/web/20210912170840/https://411mania.com/wrestling/the-undertaker-wwe-wcw-character/|url-status=live}}

To compensate for his lack of physical activity, The Undertaker became increasingly overbearing and vocal, often mouthing off with a weirdness and making sinisterly smart-aleck remarks in promos and on commentary. On the September 23, 1999, episode of SmackDown!, Mr. McMahon threatened that he would remove The Undertaker from the Unforgiven main event if he refused to participate in a casket match against Triple H. The Undertaker retorted that he did not care and maybe he would not be participating in anything WWF any longer, from there walking out on the WWF.{{cite web|url=http://www.pwwew.net/tv/smackdown/990923.htm|title=WWF SmackDown results|publisher=PWWEW.net|access-date=March 21, 2013|date=September 23, 1999|archive-date=January 20, 2018|archive-url=https://web.archive.org/web/20180120195619/http://www.pwwew.net/tv/smackdown/990923.htm|url-status=live}} In reality, Calaway went on a hiatus from the WWF in order to treat his groin injury. He made his return to action on December 14, teaming with Viscera in a losing effort against Kane and The Godfather at a house show in Coamo, Puerto Rico.{{cite web |url=http://www.thehistoryofwwe.com/99.htm |title=1999 |website=thehistoryofwwe.com |access-date=January 9, 2022 |archive-date=June 11, 2020 |archive-url=https://web.archive.org/web/20200611191606/http://www.thehistoryofwwe.com/99.htm |url-status=live }} The Undertaker was advertised on the Armageddon promotional poster to return, but meanwhile also tore his pectoral muscle, taking him out of action for almost eight months.{{cite web|url=http://www.pwinsider.com/article/54778/undertaker-royal-rumble-vickie-guerrero-and-more.html|title=Undertaker, Royal Rumble, Vickie Guerrero and more|last=Woodward|first=Buck|date=January 29, 2011|publisher=PWInsider|access-date=February 23, 2015|archive-date=March 4, 2016|archive-url=https://web.archive.org/web/20160304000229/http://www.pwinsider.com/article/54778/undertaker-royal-rumble-vickie-guerrero-and-more.html|url-status=live}}

{{see also|Brothers of Destruction}}

File:the Undertaker at WrestleMania XIX.jpg]]

In May 2000, Calaway expanded on The Undertaker gimmick, returning under a human alter ego of the gimmick—a smack-talking, redneck biker, dubbed "The American Badass", known for motorcycle-riding, tobacco chewing/spitting, and donning a sporty appearance and manner.{{cite news|url=https://books.google.com/books?id=iZqdBgAAQBAJ&dq=American+Badass+Texas+redneck+biker&pg=PA224|title=The Complete WWF Video Guide: Volume 5|access-date=February 22, 2022|work=Lulu.com|last1=Dixon|first1=James|last2=Furious|first2=Arnold|last3=Maughan|first3=Lee|date=March 29, 2014|isbn=978-1-291-81693-8 |archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003432/https://books.google.com/books?id=iZqdBgAAQBAJ&dq=American+Badass+Texas+redneck+biker&pg=PA224|url-status=live}} In stark contrast to his horror-themed and fully fictional Deadman persona, Calaway's Badass persona was only semifictional with traits and features adopted from who he is out of character—hence, why he desired to transform The Undertaker.{{cite news|url=https://bleacherreport.com/articles/2886330-the-evolution-of-the-undertakers-american-badass-character-in-wwe|title=The Evolution of The Undertaker's 'American Badass' Character in WWE|access-date=February 22, 2022|work=Bleacher Report|last=Beaston|first=Erik|date=April 13, 2020|archive-date=April 23, 2021|archive-url=https://web.archive.org/web/20210423183339/https://bleacherreport.com/articles/2886330-the-evolution-of-the-undertakers-american-badass-character-in-wwe|url-status=live}}{{cite news|url=https://www.pwtorch.com/site/2020/08/17/20-yrs-ago-wwe-raw-report-8-14-2000-the-rock-angle-stephanie-triple-h-shane-hardys-lita-undertaker-trish-guerrero-x-pac/|title=20 YRS AGO: WWE RAW REPORT (8-14-2000): The Rock, Angle, Stephanie, Triple H, Shane, Hardys, Lita, Undertaker, Trish, Guerrero, X-Pac|access-date=February 11, 2022|work=PWTorch|last=Powell|first=Jason|date=August 17, 2020|archive-date=February 11, 2022|archive-url=https://web.archive.org/web/20220211061718/https://www.pwtorch.com/site/2020/08/17/20-yrs-ago-wwe-raw-report-8-14-2000-the-rock-angle-stephanie-triple-h-shane-hardys-lita-undertaker-trish-guerrero-x-pac/|url-status=live}} While explained off screen years later for the above reasons, Calaway's sudden appearance as American Badass Undertaker after hiatus in which he left off as Deadman Undertaker was never explained within WWE storylines or the WWE's fictional universe. Rather, the expectation was for fans to just go with it.{{cite news|url=https://screenrant.com/wwe-undertaker-zombie-biker-changes-explained/|title=Why WWE Changed The Undertaker Into A Biker (Then Switched Him Back)|access-date=March 5, 2022|work=Screen Rant|last=Kennedy|first=Michael|date=March 5, 2022|archive-date=March 5, 2022|archive-url=https://web.archive.org/web/20220305223120/https://screenrant.com/wwe-undertaker-zombie-biker-changes-explained/|url-status=live}}

When The Undertaker returned near the end of the iron man match for the WWF Championship between Triple H and The Rock at Judgment Day on May 21, 2000, he took out all the members of the McMahon-Helmsley Faction, which created for a face turn after having left things off as a heel before his hiatus.{{cite news|url=https://books.google.com/books?id=TM38w278TJIC&dq=kane+chokeslam+undertaker+through+the+ring+raw&pg=PA22|title=The Undertaker: Master of Pain (see page 21 and 22)|access-date=February 10, 2022|work=Rosen Publishing|last=Bringle|first=Jennifer|date=January 1, 2012|isbn=978-1-4488-5536-0 |archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003434/https://books.google.com/books?id=TM38w278TJIC&dq=kane+chokeslam+undertaker+through+the+ring+raw&pg=PA22|url-status=live}} He also targeted their leader, then WWF Champion Triple H. At the King of the Ring pay-per-view on June 25, The Undertaker teamed with The Rock and Kane to defeat the team of Triple H, Shane McMahon and Vince McMahon. Afterward, he was booked to team with Kane to contend for the WWF Tag Team Championship. They defeated Edge and Christian, earning the right to face them the following week for the championship, which Edge and Christian retained. During an August 14 Raw is War bout against Chris Benoit, Kane became involved and betrayed The Undertaker by hitting him with two chokeslams, the second one causing the ring apron to cave in underneath The Undertaker. This incident led to another match between the two at SummerSlam on August 27, which ended in a no contest as Kane fled from the ring area after The Undertaker removed Kane's mask.PWI Staff. 2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.106)

The Undertaker then challenged Kurt Angle for the WWF Championship at Survivor Series on November 19.2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.107) Angle, however, defeated The Undertaker after he switched places with his real-life brother, Eric Angle. The Undertaker demanded and was awarded a spot in the six-man Hell in a Cell match for the WWF Championship at Armageddon on December 10. The Undertaker promised to make someone famous and did so when he performed a chokeslam on Rikishi from the roof of the cell into hay-filled cargo bed of a truck.

The Undertaker reunited with Kane as the Brothers of Destruction, issuing a challenge for the WWF Tag Team Championship once again. They received a title shot at No Way Out on February 25, 2001, facing Edge and Christian and then champions The Dudley Boyz in a tables match but were unsuccessful. The Undertaker then went on to defeat Triple H at WrestleMania X-Seven on April 1. He and Kane continued a storyline that focused on Triple H, who formed a "surprise alliance" with then WWF Champion Stone Cold Steve Austin. The Brothers of Destruction were granted an opportunity to face Triple H and Austin for their titles (Triple H was the WWF Intercontinental Champion). After The Undertaker and Kane won the WWF Tag Team Championship from Edge and Christian on the April 19 episode of SmackDown!,{{cite web|url=http://www.wwe.com/inside/titlehistory/worldtagteam/|title=World Tag Team Title History|publisher=WWE|access-date=June 21, 2009|archive-date=November 14, 2006|archive-url=https://web.archive.org/web/20061114122031/http://www.wwe.com/inside/titlehistory/worldtagteam/|url-status=live}} Triple H pinned Kane after attacking him with a sledgehammer at Backlash on April 29, where the Brothers of Destruction lost their championships.2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.108–109) With Kane injured, The Undertaker feuded briefly with Austin for his WWF Championship, but he failed to win the title at Judgment Day on May 20.

As part of "The Invasion" storyline, The Undertaker's next nemesis was Diamond Dallas Page, who was obsessively stalking The Undertaker's wife, Sara. At SummerSlam on August 19, WCW Tag Team Champions The Undertaker and Kane defeated Page and his partner Kanyon in a steel cage match to win the WWF Tag Team Championship. At Survivor Series on November 18, The Undertaker teamed with Kane, The Rock, Chris Jericho and Big Show to take on The Alliance's Stone Cold Steve Austin, Booker T, Rob Van Dam, Shane McMahon and Kurt Angle (this was the last time The Undertaker and Kane teamed until 2006). Angle pinned The Undertaker due to interference by Austin. Despite this, Team WWF won the match.

After The Alliance was defeated, The Undertaker inducted commentator Jim Ross into the Mr. McMahon: Kiss My Ass Club on the November 26 episode of Raw, which involved The Undertaker pressing the lips of Ross against McMahon's exposed buttocks, turning heel in the process.{{cite news|url=https://www.essentiallysports.com/wwe-news-the-infamous-kiss-my-a-club-of-wwe-chairman-vince-mcmahon/|title=The Infamous Kiss My A** Club of WWE Chairman Vince McMahon|access-date=February 11, 2022|work=EssentiallySports|last=Mishra|first=Prithvi|date=October 25, 2021|archive-date=February 14, 2022|archive-url=https://web.archive.org/web/20220214131351/https://www.essentiallysports.com/wwe-news-the-infamous-kiss-my-a-club-of-wwe-chairman-vince-mcmahon/|url-status=live}} In transitioning his "American Badass" biker identity into a heel, The Undertaker eventually cut his long hair short and went by the nickname "Big Evil". At Vengeance on December 9, The Undertaker defeated Rob Van Dam to win the WWF Hardcore Championship.2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.109–110)

File:Biker Taker.jpg

The Undertaker's next storyline began at the Royal Rumble on January 20, 2002, when Maven eliminated him from the Royal Rumble match by hitting him with a dropkick from behind. Subsequently, The Undertaker eliminated Maven in return and brutally assaulted him backstage. Thereafter, on an episode of SmackDown!, The Rock angered The Undertaker by mentioning his elimination at the Royal Rumble. He responded by costing The Rock the number one contendership for the Undisputed WWF Championship.{{cite news|author=Michael McAvennie|title=WWE The Yearbook: 2003 Edition|publisher=Pocket Books|year=2003|page=52}} The storyline continued when The Rock cost The Undertaker the WWF Hardcore Championship against Maven on the February 7 episode of SmackDown!.{{cite news|author=Michael McAvennie|title=WWE The Yearbook: 2003 Edition|publisher=Pocket Books|year=2003|page=56}} The two faced off at No Way Out on February 17, where The Undertaker lost due to interference from Ric Flair. This interference began a storyline with Flair, who declined a challenge to wrestle The Undertaker at WrestleMania X8 on March 17.{{cite news|first=Michael|last=McAvennie|title=WWE The Yearbook: 2003 Edition|publisher=Pocket Books|year=2003|pages=79–80}} As a result, The Undertaker assaulted Flair's son David Flair.{{cite news|author=Michael McAvennie|title=WWE The Yearbook: 2003 Edition|publisher=Pocket Books|year=2003|pages=80–81}} Flair eventually accepted the match after The Undertaker threatened to inflict the same punishment on Flair's daughter. A no-disqualification stipulation was added to the match and The Undertaker defeated Flair at WrestleMania.

File:TakerTombstone.jpg at WrestleMania X8]]

After the storyline with Flair, The Undertaker was drafted to the Raw brand after the WWF split its roster into two brands and defeated Stone Cold Steve Austin at Backlash on April 21 to become the number one contender for the Undisputed WWF Championship. Later that night, he helped Hollywood Hulk Hogan win the title against then champion Triple H. The Undertaker then defeated Hogan for the renamed WWE Undisputed Championship at Judgment Day on May 19. The next night on Raw, The Undertaker seemingly lost the WWE Undisputed Championship to Rob Van Dam; however, Raw owner Ric Flair restarted the match (Van Dam pinned The Undertaker when his foot was on the rope, thus invalidating the pin attempt) and The Undertaker defeated Van Dam to retain the championship.PWI Staff. 2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.110–111) On the July 1 episode of Raw, The Undertaker defeated Jeff Hardy in a ladder match to retain the WWE Undisputed Championship and raised Hardy's hand as a show of respect, turning face once again. The Undertaker, however, lost the title at Vengeance on July 21 to The Rock in a triple threat match that also involved Kurt Angle. On the August 29 episode of SmackDown!, The Undertaker moved to the SmackDown! brand (where he remained until the first brand extension ended in 2011), and defeated Chris Benoit and Kurt Angle in a triple threat match to become the number-one contender for the renamed WWE Championship and challenged Brock Lesnar for the title at Unforgiven on September 22 that ended in a double disqualification. Their feud carried over to No Mercy on October 20 in a Hell in a Cell match, which The Undertaker performed with a legitimately broken hand and ultimately lost to Lesnar.

The Undertaker took a break after Big Show threw him off the stage on the October 24 episode of SmackDown!, sparking a feud.{{cite news|last=McAvennie|first=Michael|title=WWE The Yearbook: 2003 Edition|publisher=Pocket Books|year=2003|page=288}} The Undertaker returned at the Royal Rumble on January 19, 2003.2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.112–113) He immediately continued his feud with Big Show and defeated him by submission at No Way Out on February 23 with a triangle choke. A-Train entered the storyline by attempting to attack The Undertaker after the match, but Nathan Jones came to his aid. The storyline resumed as The Undertaker began to train Jones to wrestle and the two were scheduled to fight Big Show and A-Train in a tag team match at WrestleMania XIX on March 30. However, Jones was removed before the match, making it a handicap match, which The Undertaker won with the help of Jones.

Over the remainder of the year, The Undertaker entered a brief feud with John Cena (defeating him at Vengeance on July 27) and was booked to have two WWE Championship opportunities. The first, on the September 4 SmackDown!, against Kurt Angle, ended in a no contest, due to interference from Brock Lesnar.{{cite news|url=http://thewrestlingestate.com/index.php/2020/11/18/30-greatest-undertaker-matches/|title=30 Greatest Undertaker Matches|access-date=February 11, 2022|work=TheWrestlingState|last=Corrigan|first=John|date=November 18, 2020|archive-date=February 15, 2022|archive-url=https://web.archive.org/web/20220215000054/http://thewrestlingestate.com/index.php/2020/11/18/30-greatest-undertaker-matches/|url-status=live}} The second, at No Mercy on October 19, was a Biker Chain match between The Undertaker and Lesnar, which Lesnar won with the help of Vince McMahon.PWI Staff. 2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.113–114) This match resulted in a feud with McMahon, culminating at Survivor Series on November 16 where The Undertaker lost a Buried Alive match against McMahon when Kane interfered. The Undertaker disappeared for some time following this match, with Kane claiming that he was "dead and buried forever".{{cite news|url=https://bleacherreport.com/articles/478721-the-devils-favorite-feud-the-history-of-the-undertaker-vs-kane|title=WWE Hell in a Cell Preview: The History Of The Undertaker Vs. Kane Feud (section 6 of 9)|access-date=February 11, 2022|work=Bleacher Report|last=Brewer|first=Josh|date=September 30, 2010|archive-date=February 14, 2022|archive-url=https://web.archive.org/web/20220214234440/https://bleacherreport.com/articles/478721-the-devils-favorite-feud-the-history-of-the-undertaker-vs-kane|url-status=live}}

File:Undertaker2.jpg

In the storyline leading up to WrestleMania XX, Kane was tormented by horror-themed mind games, paranormal activities, and spooking vignettes proclaiming The Undertaker's Deadman return. The first was during the Royal Rumble when The Undertaker's bells tolled, distracting Kane and allowing Booker T to eliminate him. Accompanied by Paul Bearer at WrestleMania XX, The Undertaker resurrected his Deadman identity, defeating Kane in a singles match.2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.115–116) Introduced was a more dramatic, theatrical and supernatural Deadman than in years past, his presence, mannerisms, and entrances significantly elaborated on as well, such as with more intensity, special effects and rising and falling flames.{{cite news|url=https://bleacherreport.com/articles/2827831-how-triple-h-undertaker-shawn-michaels-crafted-epic-4-year-wrestlemania-saga|title=How Triple H, Undertaker, Shawn Michaels Crafted Epic 4-Year WrestleMania Saga|access-date=February 16, 2022|work=Bleacher Report|last=Wong|first=Kevin|date=April 4, 2019|archive-date=February 16, 2022|archive-url=https://web.archive.org/web/20220216073251/https://bleacherreport.com/articles/2827831-how-triple-h-undertaker-shawn-michaels-crafted-epic-4-year-wrestlemania-saga|url-status=live}} At the same time, The Undertaker maintained elements of his American Badass identity, thus a composite character more humanized than all of his previous Deadman incarnations{{cite news|url=https://www.givemesport.com/87975316-the-undertaker-the-greatest-moments-in-the-deadmans-hall-of-fame-career|title=The Undertaker: The greatest moments in The Deadman's Hall of Fame career|access-date=February 23, 2022|work=GiveMeSport|last=Rose|first=Ash|date=February 21, 2022|archive-date=February 24, 2022|archive-url=https://web.archive.org/web/20220224021001/https://www.givemesport.com/87975316-the-undertaker-the-greatest-moments-in-the-deadmans-hall-of-fame-career|url-status=live}} (The Undertaker would present in this particular hybrid Deadman form until No Mercy 2005 when Randy Orton sealed him in a casket and set it on fire). At Judgment Day, The Undertaker defeated Booker T. One week later, Paul Heyman ordered The Dudley Boyz to kidnap Bearer.{{cite news|url=https://www.pwinsider.com/article/75883/william-paul-bearer-moody-passes-away.html?p=1|title=WILLIAM 'PAUL BEARER' MOODY PASSES AWAY|access-date=February 13, 2022|work=PWInsider|last=Johnson|first=Mike|date=May 3, 2013|archive-date=February 13, 2022|archive-url=https://web.archive.org/web/20220213085314/https://www.pwinsider.com/article/75883/william-paul-bearer-moody-passes-away.html?p=1|url-status=live}}{{cite news|url=https://books.google.com/books?id=TM38w278TJIC&dq=Heyman+took+control+of+Undertaker+kidnap+Paul+Bearer&pg=PA24|title=Undertaker: Master of Pain|access-date=September 25, 2021|work=Rosen Publishing|last=Bringle|first=Jennifer|date=December 15, 2011|isbn=9781448855360|archive-date=February 12, 2024|archive-url=https://web.archive.org/web/20240212181045/https://books.google.com/books?id=TM38w278TJIC&dq=Heyman+took+control+of+Undertaker+kidnap+Paul+Bearer&pg=PA24#v=onepage&q=Heyman%20took%20control%20of%20Undertaker%20kidnap%20Paul%20Bearer&f=false|url-status=live}} Thus, Heyman "took control" of Undertaker. At The Great American Bash, The Undertaker fought a handicap match against The Dudley Boyz, with the stipulation that if he did not lay down and purposely lose, Heyman would bury Paul Bearer in cement. The Undertaker won and stopped Heyman from burying Bearer, but after claiming Bearer was merely a liability he had no use for, buried him himself.

The Undertaker began a feud with then WWE Champion John "Bradshaw" Layfield (JBL) by challenging him to a title match at SummerSlam, which The Undertaker lost by disqualification. At No Mercy, The Undertaker and JBL competed in the first-ever Last Ride match, although The Undertaker lost after Heidenreich interfered. After defeating Heidenreich in a match at Survivor Series,PWI Staff. 2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.116–117) The Undertaker turned his focus to the WWE Championship once again. Along with Eddie Guerrero and Booker T, he challenged JBL to a championship rematch at Armageddon in a fatal four-way match, in which The Undertaker was unsuccessful, again due to Heidenreich's interference. The feud culminated in a casket match between The Undertaker and Heidenreich at the Royal Rumble, where The Undertaker sealed Heidenreich in a casket for the victory.

Soon after, Randy Orton challenged The Undertaker to a match at WrestleMania 21, uppishly proclaiming that he would end his WrestleMania winning Streak.{{cite news|url=https://books.google.com/books?id=TM38w278TJIC&dq=Randy+Orton+claiming+he+would+end+the+undertaker%27s+streak&pg=PA25|title=Undertaker: Master of Pain|access-date=September 25, 2021|work=Rosen Publishing|last=Bringle|first=Jennifer|date=December 15, 2011|isbn=9781448855360|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003431/https://books.google.com/books?id=TM38w278TJIC&dq=Randy+Orton+claiming+he+would+end+the+undertaker%27s+streak&pg=PA25|url-status=live}} Even with help from his father, Orton lost as The Undertaker improved his WrestleMania record to 13–0. After a two-month hiatus, The Undertaker returned on the June 16 episode of SmackDown!, but lost to JBL due to interference from Randy Orton, who was drafted to SmackDown! as part of the draft lottery.{{cite news|url=https://wrestlecrap.com/inductions/ortons-vs-undertaker/|title=INDUCTION: THE ORTONS VS. THE UNDERTAKER – POSSESSION IS 9/10S OF THE LAW, BUT ONLY 1/10 OF WHAT MADE THIS FEUD SO STUPID|access-date=February 13, 2022|work=WrestleCrap|last=Donnell|first=Arto|date=October 29, 2015|archive-date=February 12, 2024|archive-url=https://web.archive.org/web/20240212181140/https://www.wrestlecrap.com/inductions/the-undertaker-vs-the-ortons/|url-status=live}} Despite his interference, the Randy Orton/Undertaker feud was put on the back burner until late summer of that year, resulting from Orton on the injured list.{{cite news|url=https://books.google.com/books?id=wkw7TGfHYPMC&dq=Randy+Orton+new+draft+pick+to+smackdown+june+2005+jbl&pg=PA159|title=Wrestling's Sinking Ship: What Happens To An Industry Without Competition (p. 159)|access-date=February 13, 2022|work=Lulu.com|last=Hamilton|first=Ian|date=January 1, 2006|isbn=9781411612105|archive-date=February 12, 2024|archive-url=https://web.archive.org/web/20240212181050/https://books.google.com/books?id=wkw7TGfHYPMC&dq=Randy+Orton+new+draft+pick+to+smackdown+june+2005+jbl&pg=PA159#v=onepage&q=Randy%20Orton%20new%20draft%20pick%20to%20smackdown%20june%202005%20jbl&f=false|url-status=live}}

In the meantime and in one of the most controversial moments in WWE history on an episode of SmackDown! taped on July 4, 2005 (aired on July 7), SmackDown! General Manager Theodore Long scheduled Muhammad Hassan in a match against The Undertaker at The Great American Bash, and placed Daivari in a match that night against Undertaker: Undertaker quickly defeated Daivari. After the match, however, Hassan began to "pray" on the ramp, summoning five masked men, dressed in black shirts, ski-masks and camouflage pants. Armed with clubs and a piano wire, the masked men assaulted and choked out The Undertaker before Hassan then placed The Undertaker in a camel clutch. Afterward, the masked men lifted Daivari above their heads and carried him away. Three days later, the London bombings took place. The footage aired unedited on UPN in the United States and on The Score in Canada with an advisory warning shown several times during the broadcast. It was removed from the Australian and European (including in the United Kingdom) broadcasts.{{cite web|first=Adam|last=Martin|title=Notes regarding segment on SmackDown with Hassan, Daivari & Taker|url=http://www.wrestleview.com/news2005/1120848867.shtml|publisher=WrestleView.com|access-date=July 8, 2007|date=July 8, 2005|archive-date=November 28, 2021|archive-url=https://web.archive.org/web/20211128075151/http://www.wrestleview.com/news2005/1120848867.shtml|url-status=live}}

The angle elicited national attention in the New York Post, TV Guide, Variety and other major media outlets. In response to the criticism, UPN decided that it would monitor the storyline closely and that it did not want the Hassan character on its network that week.{{cite web|title=New York Post and Variety cover WWE "terrorist" angle; UPN speaks up|url=http://www.wrestleview.com/news2005/1121217332.shtml|publisher=WrestleView.com|access-date=July 8, 2007|archive-date=July 8, 2018|archive-url=https://web.archive.org/web/20180708133755/http://www.wrestleview.com/news2005/1121217332.shtml|url-status=live}} In a promo hosted on WWE's website—UPN had edited it from the July 14, 2005 episode of SmackDown!—Hassan reiterated that he was an Arab American and that the American people automatically and unfairly assumed that he was a terrorist. Despite being in character, he referred to the real-world media coverage of the storyline, singling out the New York Post's Don Kaplan by name and denouncing his description of the events on SmackDown!, such as Kaplan's comment of the masked men being "Arabs in ski masks". On the July 14, 2005 episode of SmackDown!, Hassan's absence was explained by a statement delivered by his attorney, Thomas Whitney, that Hassan refused to appear on the show until The Great American Bash due to the way he was treated by the American media and WWE fans.

It was revealed in late July 2005 that UPN had pressured WWE to keep Hassan off their network, effectively removing him from SmackDown!.{{cite news|first=Jay|last=Flannagan|title=UPN Bans Muhammad Hassan From WWE SmackDown|url=http://www.wrestleview.com/news2005/1121975573.shtml|publisher=WrestleView.com|access-date=July 8, 2007|date=July 21, 2005|archive-date=February 19, 2022|archive-url=https://web.archive.org/web/20220219215406/http://www.wrestleview.com/news2005/1121975573.shtml|url-status=live}} Undertaker defeated Hassan at The Great American Bash to become the number one contender to the World Heavyweight Championship. After the match, The Undertaker delivered a Last Ride through an open stage ramp onto a concrete floor to Hassan. It was reported that Hassan sustained serious injuries and had to be rushed to a nearby medical facility, writing Hassan off television.{{cite news|author=PWI Staff|title=Pro Wrestling Illustrated presents: 2007 Wrestling almanac & book of facts|work="Wrestling's historical cards"|publisher=Kappa Publishing|year=2007|pages=118}} Several days later, Long (kayfabe) banned Hassan from SmackDown!. It was revealed years later that Hassan was about to receive a major push by winning the World Heavyweight Championship from Batista at SummerSlam and thus breaking Randy Orton's record for being the youngest World Heavyweight Champion in WWE history.{{cite web |url=http://bleacherreport.com/articles/641490-wwes-pushed-to-punished-edition-three-muhammad-hassn |publisher=Bleacher Report |title=WWE's Pushed to Punished Edition Three: Muhammad Hassan |access-date=February 27, 2016 |date=March 22, 2011 |archive-date=March 5, 2016 |archive-url=https://web.archive.org/web/20160305194730/http://bleacherreport.com/articles/641490-wwes-pushed-to-punished-edition-three-muhammad-hassn |url-status=live }}

On the following episode of SmackDown!, The Undertaker lost to JBL in a number-one contender's match, once again due to interference from Orton, reviving their feud that was put on hiatus.{{cite news|url=https://bleacherreport.com/articles/539045-cvc-snakes-and-demons-why-randy-orton-vs-undertaker-was-the-best-feud|title=Snakes and Demons: Why Randy Orton Vs. Undertaker Is The Best Feud Ever (CvC)|access-date=February 13, 2022|work=Bleacher Report|last=Gartland|first=Ben|date=December 8, 2010|archive-date=February 14, 2022|archive-url=https://web.archive.org/web/20220214013558/https://bleacherreport.com/articles/539045-cvc-snakes-and-demons-why-randy-orton-vs-undertaker-was-the-best-feud|url-status=live}} At SummerSlam, Orton defeated The Undertaker in a WrestleMania rematch. The storyline intensified as the two tried to get into the head of one another with dark mind game tactics and use of caskets, leading to a handicap casket match at No Mercy, in which The Undertaker lost to Randy and his father "Cowboy" Bob Orton. After the match, the Ortons poured gasoline on the casket and set it on fire (a throwback moment to one of The Undertaker's most infamous attacks received and done by Kane doing the same to him at the 1998 Royal Rumble). When the charred casket was opened, however, The Undertaker was absent, presented as having vanished.PWI Staff. 2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.118)

The Undertaker resurrected at the Survivor Series when the druids delivered a casket that was struck by lightning and went up in flames. The Undertaker then burst from the flaming casket in rage, battering and brutalizing an entire ring full of wrestlers as a message to Orton. Here, he reappeared still in hybrid form but with lessened Badass characteristics, eliminating several elements of his biker identity so that his Deadman side projected, most notably, replacing loose-fitting cargo pants with his Deadman spandex, and less use of the Last Ride finisher.2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p. 119) The Undertaker returned on SmackDown! in early December to haunt Orton and set up a Hell in a Cell match at Armageddon. After The Undertaker won their brutal Hell in a Cell encounter, in effect, settling his 9 month long feud with Orton, Calaway took a brief hiatus from professional wrestling.

File:Taker-WM22.jpg]]

In January 2006 at the Royal Rumble, The Undertaker returned on a horse-drawn cart during Kurt Angle's celebration of his World Heavyweight Championship defense against Mark Henry. In this appearance, The Undertaker signaled for a title shot by using his supernatural powers to collapse the wrestling ring that Angle stood in as a means to spook him. As part of their storyline angle, The Undertaker lost his match with Angle at No Way Out after a 30-minute bout—described as underrated and among Undertaker's top matches, in which he versatilely took to a more ground-based submission style to combat Angle's trademarked freestyle wrestling.{{cite news|url=https://bleacherreport.com/articles/1205441-wwe-no-way-out-2006-top-5-moments-from-kurt-angle-vs-undertaker|title=WWE No Way out 2006: Top 5 Moments from Kurt Angle vs. Undertaker|work=Bleacher Report|access-date=February 26, 2022|last=Watry|first=Justin|date=June 1, 2012|archive-date=February 26, 2022|archive-url=https://web.archive.org/web/20220226125947/https://bleacherreport.com/articles/1205441-wwe-no-way-out-2006-top-5-moments-from-kurt-angle-vs-undertaker|url-status=live}}{{cite news|url=https://bleacherreport.com/articles/2352040-wwe-classic-of-the-week-the-undertaker-vs-kurt-angle-from-no-way-out-2006|title=WWE Classic of the Week: The Undertaker vs. Kurt Angle from No Way out 2006|work=Bleacher Report|access-date=February 26, 2022|last=Beaston|first=Erik|date=February 3, 2015|archive-date=February 26, 2022|archive-url=https://web.archive.org/web/20220226125949/https://bleacherreport.com/articles/2352040-wwe-classic-of-the-week-the-undertaker-vs-kurt-angle-from-no-way-out-2006|url-status=live}} The Undertaker cornered Angle after the match and told him he was not finished with him. In a rematch with Angle (similarly described as underrated and among The Undertaker's top matches that utilized the wrestling styles of their previous encounter on the March 3 episode of SmackDown!) Henry attacked The Undertaker from behind, costing him the title. This led to The Undertaker challenging Henry to a casket match at WrestleMania 22 and Henry vowing to end The Undertaker's WrestleMania winning Streak. The match resulted in The Undertaker sealing Henry in the casket, winning the match and extending his streak to 14–0 at WrestleMania.{{cite news|url=https://bleacherreport.com/articles/1103860-wwe-wrestlemania-22-top-10-moments-from-an-excellent-show-in-chicago|title=WWE WrestleMania 22: Top 10 Moments from an Excellent Show in Chicago|work=Bleacher Report|access-date=February 26, 2022|last=Watry|first=Justin|date=March 14, 2012|archive-date=February 26, 2022|archive-url=https://web.archive.org/web/20220226131337/https://bleacherreport.com/articles/1103860-wwe-wrestlemania-22-top-10-moments-from-an-excellent-show-in-chicago|url-status=live}} During a rematch on the next episode of SmackDown!, The Undertaker was assaulted by the debuting Great Khali.{{cite news|url=https://bleacherreport.com/articles/1714307-wwe-pushed-to-punished-edition-35-the-punjabi-plunge-of-the-great-khali|title=WWE Pushed to Punished, Edition 35: The Punjabi Plunge of the Great Khali|work=Bleacher Report|access-date=February 26, 2022|last=Matthews|first=Graham|date=August 11, 2013|archive-date=February 16, 2022|archive-url=https://web.archive.org/web/20220216065924/https://bleacherreport.com/articles/1714307-wwe-pushed-to-punished-edition-35-the-punjabi-plunge-of-the-great-khali|url-status=live}}

The Undertaker was not heard from until the May 5 episode of SmackDown! when Theodore Long delivered a challenge from The Undertaker to Khali for a match at Judgment Day. The Undertaker lost to Khali at Judgment Day,2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.121){{cite web|url=http://www.wwe.com/shows/judgmentday/history/2006/matches/23848443/results/ |title=The Great Khali makes Undertaker rest in peace|date=May 21, 2006|author=Ed Williams III|access-date=January 5, 2008|publisher=WWE|url-status=dead|archive-url=https://web.archive.org/web/20080103092353/http://www.wwe.com/shows/judgmentday/history/2006/matches/23848443/results/|archive-date=January 3, 2008}} and he did not appear again until the July 7 episode of SmackDown! when he accepted Khali's challenge to a Punjabi Prison match at The Great American Bash. However, Khali was removed from the match due to not being medically cleared. He was thus replaced by then ECW World Champion Big Show, over whom The Undertaker gained the victory.Archived at [https://ghostarchive.org/varchive/youtube/20211212/Iy5AukI0Kbg Ghostarchive]{{cbignore}} and the [https://web.archive.org/web/20151118163934/https://www.youtube.com/watch?v=Iy5AukI0Kbg&gl=US&hl=en Wayback Machine]{{cbignore}}: {{cite AV media|url=https://www.youtube.com/watch?v=Iy5AukI0Kbg|title=5 Undertaker matches you've never seen before: 5 Things|date=November 18, 2015|via=YouTube}}{{cbignore}} In storyline, Theodore Long replaced Khali with Big Show as punishment for an attack on The Undertaker shortly before the match. Khali was then challenged by The Undertaker to a Last Man Standing Match for SummerSlam after interfering in The Undertaker's match with then World Heavyweight Champion King Booker. Khali refused the challenge but Long scheduled the Last Man Standing Match ahead of time, for the August 18 episode of SmackDown! instead. The Undertaker won the match by striking Khali with steel stairs and finishing him with a chokeslam. It was Khali's first defeat and effectively ended his feud with The Undertaker.{{cite news|url=https://insidepulse.com/2006/08/11/50278/|title=The (Early) SmackDown Report|access-date=February 16, 2022|work=Inside Pulse|last=Hepple|first=Troy|date=August 11, 2006|archive-date=February 16, 2022|archive-url=https://web.archive.org/web/20220216100110/https://insidepulse.com/2006/08/11/50278/|url-status=live}}{{cite news|url=https://bleacherreport.com/articles/1714307-wwe-pushed-to-punished-edition-35-the-punjabi-plunge-of-the-great-khali|title=WWE Pushed to Punished, Edition 35: The Punjabi Plunge of the Great Khali|access-date=February 16, 2022|work=Bleacher Report|last=Matthews|first=Graham|date=August 11, 2013|archive-date=February 16, 2022|archive-url=https://web.archive.org/web/20220216065924/https://bleacherreport.com/articles/1714307-wwe-pushed-to-punished-edition-35-the-punjabi-plunge-of-the-great-khali|url-status=live}}

The Undertaker's next match was with then United States Champion Mr. Kennedy at No Mercy, but was disqualified in the match after he hit Kennedy with the championship belt.PWI Staff. 2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.122) On the November 3 episode of SmackDown!, The Undertaker reunited with Kane to reform the Brothers of Destruction for the first time in five years, defeating reluctant opposition in the form of Mr. Kennedy and Montel Vontavious Porter (MVP), with whom Kane was feuding with at the time.{{cite news|url=https://insidepulse.com/2006/11/03/62499/|title=Smackdown Preview for November 3, 2006|access-date=February 15, 2022|work=Inside Pulse|last=Michaels|first=Matthew|date=November 3, 2006|archive-date=February 16, 2022|archive-url=https://web.archive.org/web/20220216064214/https://insidepulse.com/2006/11/03/62499/|url-status=live}} As part of the storyline, Kennedy defeated The Undertaker in a First Blood match at Survivor Series after interference from MVP, but finally defeated Kennedy in a Last Ride match at Armageddon. The two continued to feud into 2007 as Kennedy cost The Undertaker two World Heavyweight Championship opportunities for a championship match at the Royal Rumble.2007 Wrestling almanac & book of facts. "Wrestling's historical cards" (p.130) However, The Undertaker eventually qualified for the 2007 Royal Rumble match, by winning a battle royal on the January 26 episode of SmackDown!.{{cite web|url=http://slam.canoe.com/Slam/Wrestling/2007/01/27/3459986.html|archive-url=https://web.archive.org/web/20170724035545/http://slam.canoe.com/Slam/Wrestling/2007/01/27/3459986.html|url-status=dead|archive-date=July 24, 2017|title=Smackdown: The Rumble comes early|work=Slam! Sports|publisher=Canoe.com|first=Andy|last=McNamara|date=January 27, 2007|access-date=February 24, 2019}}

File:Undertaker with Fire.jpg

The Undertaker won his first Royal Rumble match on January 28, in doing so becoming the first man to enter the Rumble at number 30 and win the match, after lastly eliminating Shawn Michaels.{{cite web|url=http://www.wwe.com/shows/royalrumble/history/2007/matches/35535102/results/|publisher=WWE|title=A Phenom-enal Rumble|last=Dee|first=Louie|date=January 28, 2007|access-date=August 23, 2007|url-status=dead|archive-url=https://web.archive.org/web/20071217110330/http://www.wwe.com/shows/royalrumble/history/2007/matches/35535102/results/|archive-date=December 17, 2007}} On the February 5 episode of Raw, The Undertaker elected to face World Heavyweight Champion Batista at WrestleMania 23 on April 1, before attacking him with the chokeslam.{{cite web|url=http://slam.canoe.com/Slam/Wrestling/2007/02/06/3539808.html|archive-url=https://web.archive.org/web/20160310030625/http://slam.canoe.com/Slam/Wrestling/2007/02/06/3539808.html|url-status=dead|archive-date=March 10, 2016|title=Raw: Mania main events all set|work=SLAM! Sports|publisher=Canadian Online Explorer|first=Dave|last=Plummer|date=February 5, 2007|access-date=January 22, 2019}} At No Way Out on February 18, The Undertaker and Batista reluctantly teamed together to face John Cena and Shawn Michaels, but lost after Batista gained revenge on The Undertaker by hitting him with a spinebuster, allowing Cena to pin him.{{cite web|url=http://www.wwe.com/shows/nowayout/history/2007/matches/34656681/results/|archive-url=https://web.archive.org/web/20080121044611/http://www.wwe.com/shows/nowayout/history/2007/matches/34656681/results/|title=Payback|first=Brett|last=Hoffman|publisher=WWE|date=February 18, 2007|archive-date=January 21, 2008|access-date=March 5, 2008}} At WrestleMania 23, The Undertaker defeated Batista to win his first World Heavyweight Championship and extend his Streak to 15–0.{{cite web|last1=Plummer|first1=Dale|last2=Tylwalk|first2=Nick|date=April 1, 2007|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2007/04/15/4024168.html|archive-url=https://archive.today/20120530090525/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2007/04/15/4024168.html|url-status=usurped|archive-date=May 30, 2012|title=Undertaker the champ, McMahon bald|access-date=February 22, 2008|work=Slam! Sports|publisher=Canadian Online Explorer}} The Undertaker faced Batista in a rematch at Backlash on April 29, this time in a Last Man Standing match. The match ended in a draw after neither man got to their feet by the referee's count of ten, meaning The Undertaker retained the championship.{{cite web|first=Brian|last=Elliott|date=April 29, 2007|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2007/04/29/4140920.html|archive-url=https://archive.today/20120718153708/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2007/04/29/4140920.html|url-status=usurped|archive-date=July 18, 2012|title=No filler makes for a consistent Backlash|publisher=Canadian Online Explorer|work=Slam! Sports|access-date=September 24, 2009}} The Undertaker and Batista then fought once again in a steel cage match on the May 11 episode of SmackDown! that also ended in a draw when both men's feet touched the floor at the same time. After the match, Mark Henry made his return by assaulting an already battered The Undertaker, after which Edge ran to the ring and cashed in his Money in the Bank briefcase, forcing The Undertaker into a second title defense. Although he kicked out of two quick pin attempts, The Undertaker was pinned by Edge after two spears and lost the World Heavyweight Championship.{{cite web|url=http://www.wwe.com/shows/smackdown/archive/05112007|title=In with the new|date=May 11, 2007|first=Noah|last=Starr|publisher=WWE|access-date=November 17, 2007| archive-url= https://web.archive.org/web/20071121221935/http://www.wwe.com/shows/smackdown/archive/05112007| archive-date= November 21, 2007| url-status=dead}} After this match, The Undertaker took time off due to a torn right biceps.{{cite web|url=http://www.mikemooneyham.com/2007/05/20/wwe-beset-by-injuries/|title=WWE beset by injuries|work=The Wrestling Gospel|first=Mike|last=Mooneyham|date=May 20, 2007|access-date=January 22, 2019|archive-date=February 20, 2022|archive-url=https://web.archive.org/web/20220220094018/http://www.mikemooneyham.com/2007/05/20/wwe-beset-by-injuries/|url-status=live}}

File:Undertaker WHC.jpg at WrestleMania XXIV]]

During his rehabilitation, Henry bragged about his assault on The Undertaker, until vignettes began playing that promoted The Undertaker's return. The Undertaker returned at Unforgiven on September 16, defeating Henry.{{cite web|url=http://www.wwe.com/shows/unforgiven/matches/|title=Unforgiven 2007 Results|access-date=September 16, 2007|publisher=WWE|archive-date=September 2, 2006|archive-url=https://web.archive.org/web/20060902112331/http://www.wwe.com/shows/unforgiven/matches/|url-status=live}} Batista and The Undertaker reignited their feud at Cyber Sunday on October 28 with the fans choosing the special guest referee to be Stone Cold Steve Austin, however, Batista retained the World Heavyweight Championship.{{cite web|url=http://www.pwwew.net/ppv/wwf/october/cyber2007.htm|title=Cyber Sunday 2007 Results|access-date=November 19, 2007|publisher=PWWEW.net|archive-date=June 12, 2010|archive-url=https://web.archive.org/web/20100612165937/http://pwwew.net/ppv/wwf/october/cyber2007.htm|url-status=live}} They battled again in a Hell in a Cell match at Survivor Series on November 18, where Edge returned and interfered to help Batista retain the World Heavyweight Championship.{{cite web|first=Louie|last=Dee|url=http://www.wwe.com/shows/survivorseries/history/2007/matches/4334964/results/|title=On the Edge of Hell|access-date=November 19, 2007|date=November 18, 2007|publisher=WWE|url-status=dead|archive-url=https://web.archive.org/web/20081031145013/http://www.wwe.com/shows/survivorseries/history/2007/matches/4334964/results/|archive-date=October 31, 2008}} In response to this, The Undertaker delivered a Tombstone Piledriver to General Manager Vickie Guerrero on the November 23 episode of SmackDown!, sending her to the hospital. Returning assistant-General Manager Theodore Long declared a triple threat match for the title between the three men at Armageddon on December 16, which Edge won after interference from The Major Brothers.{{cite web|url=http://www.wwe.com/shows/armageddon/history/2007/matches/554660422/results/|archive-url=https://web.archive.org/web/20090330075654/http://www.wwe.com/shows/armageddon/history/2007/matches/554660422/results/|url-status=dead|title=Edge's "three-meditated" attack to perfection|first=Mike|last=McAvennie|archive-date=March 30, 2009|access-date=December 29, 2007|date=December 16, 2007|publisher=WWE}}

At the Royal Rumble on January 27, 2008, The Undertaker competed in the Royal Rumble match itself, entering at number 1, but eliminated by Shawn Michaels after lasting for most of the bout.{{cite web |last1=Plummer |first1=Dale |last2=Tywalk |first2=Nick |url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/01/28/4797664.html |archive-url=https://archive.today/20120629175015/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/01/28/4797664.html |url-status=usurped |archive-date=June 29, 2012 |title=Cena wins Rumble in surprise return |access-date=January 29, 2008 |date=January 28, 2008 |work=Slam! Sports |publisher=Canadian Online Explorer}} At No Way Out on February 17, The Undertaker defeated Batista, Finlay, The Great Khali, MVP and Big Daddy V in the SmackDown Elimination Chamber match to become the number one contender for Edge's World Heavyweight Championship at WrestleMania XXIV on March 30.{{cite web|url=http://www.wwe.com/shows/nowayout/history/2008/matches/6364982/results/ |access-date=February 17, 2008 |title=The Deadman doubles down |publisher=WWE |last=Dee |first=Louis |date=February 17, 2008 |url-status=dead |archive-url=https://web.archive.org/web/20090225063218/http://www.wwe.com/shows/nowayout/history/2008/matches/6364982/results/ |archive-date=February 25, 2009 }} At WrestleMania, The Undertaker defeated Edge with the Hell's Gate submission hold to win his second World Heavyweight Championship in what was his 16th WrestleMania win.{{cite web|url=http://www.wwe.com/shows/wrestlemania/matches/6208634/results/|archive-url=https://web.archive.org/web/20080405163823/http://www.wwe.com/shows/wrestlemania/matches/6208634/results/|archive-date=April 5, 2008|title=Sweet Sixteen|date=March 30, 2008|first=Craig|last=Tello|access-date=April 10, 2008|publisher=WWE}} In a WrestleMania rematch, The Undertaker defeated Edge once again at Backlash on April 27 to retain the World Heavyweight Championship.{{cite web |url=http://www.wwe.com/shows/backlash/matches/6347966/results/|access-date=May 2, 2008|title=Second verse, same as the first|last=Dee|first=Louie|publisher=WWE|date=April 27, 2008|archive-url=https://web.archive.org/web/20080501145452/http://www.wwe.com/shows/backlash/matches/6347966/results/ |archive-date=May 1, 2008}} Vickie Guerrero then banned The Undertaker's Hell's Gate submission hold and stripped him of the World Heavyweight Championship on the May 2 episode of SmackDown.{{cite web|url=http://www.wwe.com/shows/smackdown/archive/05022008/articles/titleturmoil|title=Title turmoil|date=May 2, 2008|last=Dee|first=Louis|access-date=May 3, 2008|publisher=WWE|archive-date=February 20, 2022|archive-url=https://web.archive.org/web/20220220185633/https://www.wwe.com/shows/smackdown/archive/05022008/articles/titleturmoil|url-status=live}} The Undertaker battled Edge for the vacant title at Judgment Day on May 18, which he won by countout. Guerrero ordered that the title remain vacant, because titles could not change hands in this way.{{cite web|first=Bob|last=Kapur|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/05/18/5609326.html|archive-url=https://archive.today/20120718052924/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/05/18/5609326.html|url-status=usurped|archive-date=July 18, 2012|title=Judgment Day spoils streak of good shows|access-date=June 16, 2008|date=May 18, 2008|work=Slam! Sports|publisher=Canadian Online Explorer}} Edge and The Undertaker faced each other again for the vacant championship at One Night Stand on June 1 in a Tables, Ladders, and Chairs match, which The Undertaker lost after interference from La Familia. As a result of the stipulation, The Undertaker was forced to leave WWE.{{cite web|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/05/30/5721341.html|archive-url=https://archive.today/20120724193637/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/05/30/5721341.html|url-status=usurped|archive-date=July 24, 2012|title=One Night Stand WWE's best this year|date=May 30, 2008|last=Mackinder|first=Matt|access-date=March 28, 2009|work=Slam! Sports|publisher=Canadian Online Explorer}}

File:Undertaker at Wrestlemania 25 cropped.jpg at WrestleMania 25]]

On the July 25 episode of SmackDown, Vickie Guerrero reinstated The Undertaker and scheduled Edge to face him at SummerSlam on August 17 in a Hell in a Cell match,{{cite web|url=http://www.wwe.com/shows/smackdown/archive/07252008/|title=SmackDown: A woman's scorn, a Deadman reborn|access-date=June 25, 2008|archive-date=August 6, 2008|archive-url=https://web.archive.org/web/20080806083454/http://www.wwe.com/shows/smackdown/archive/07252008/|url-status=live}} which The Undertaker won. After the match, The Undertaker chokeslammed Edge from the top of a ladder and through the ring canvas.{{cite web|url=http://www.wwe.com/shows/summerslam/matches/6541940/results/|title=Unleashed in Hell|last=DiFino|first=Lennie|date=August 17, 2008|publisher=WWE|access-date=August 18, 2008|archive-url=https://web.archive.org/web/20080822055025/http://www.wwe.com/shows/summerslam/matches/6541940/results/ |archive-date=August 22, 2008}} Following this match, Guerrero tried making a peace offering with The Undertaker on SmackDown by apologizing, but The Undertaker told her that he was not the forgiving kind. At Unforgiven on September 7, as The Undertaker approached the ring to "take Guerrero's soul" and seal her in a casket, Big Show, who appeared at first to be aiding The Undertaker ended up assaulting him.{{cite web|url=http://www.wwe.com/shows/unforgiven/matches/bigshowspeaks/results/|title=Big Show lends Guerrero a giant hand|date=September 7, 2008|publisher=WWE|access-date=September 7, 2008|url-status=dead|archive-url=https://web.archive.org/web/20080910044919/http://www.wwe.com/shows/unforgiven/matches/bigshowspeaks/results/|archive-date=September 10, 2008}} Resulting from that, The Undertaker and Big Show faced each other in a match at No Mercy on October 5, where Big Show won by knockout.{{cite web|url=http://www.wwe.com/shows/nomercy/matches/8101498/results/|title=The knockout heard 'round the WWE Universe|last=Burdick|first=Michael|date=October 5, 2008|publisher=WWE|access-date=October 6, 2008|url-status=dead|archive-url=https://web.archive.org/web/20081008104418/http://www.wwe.com/shows/nomercy/matches/8101498/results/|archive-date=October 8, 2008}} At Cyber Sunday on October 26, The Undertaker defeated Big Show in a Last Man Standing match after choking him out with Hell's Gate.{{cite web|url=http://www.wwe.com/shows/cybersunday/matches/8320770/results/|access-date=September 17, 2009|date=October 26, 2008|last=Passero|first=Mitch|title=Deadman's revenge|publisher=WWE|url-status=dead|archive-url=https://web.archive.org/web/20090630182014/http://www.wwe.com/shows/cybersunday/matches/8320770/results/|archive-date=June 30, 2009}} At the same time, The Undertaker was engaged in a short feud with Jeff Hardy, who interfered during his match with Vladimir Kozlov on the November 7 episode of SmackDown. Hardy defeated The Undertaker in an Extreme Rules match the following week on SmackDown due to interference from Big Show. The Undertaker then went on to defeat Big Show in a casket match at Survivor Series on November 23 and again in a steel cage match by submission on the December 5 episode of SmackDown to end their feud.{{cite web|url=http://www.wwe.com/shows/survivorseries/2008/matches/8641756|access-date=May 5, 2012|date=November 23, 2008|title=Undertaker def. Big Show (Casket Match)|publisher=WWE|archive-date=September 21, 2016|archive-url=https://web.archive.org/web/20160921042528/http://www.wwe.com/shows/survivorseries/2008/matches/8641756|url-status=live}} At No Way Out on February 15, 2009, The Undertaker was part of the WWE Championship Elimination Chamber match along with Triple H, Jeff Hardy, Big Show, Vladimir Kozlov and Edge; however, he was unsuccessful at winning the match as he was the runner-up behind Triple H.{{cite news|url=https://bleacherreport.com/articles/124676-2009-wwe-no-way-out-voices-and-chambers|title=2009 WWE No Way Out: Voices and Chambers|work=Bleacher Report|access-date=February 26, 2022|last=Robinson|first=Michael|date=February 15, 2009|archive-date=February 26, 2022|archive-url=https://web.archive.org/web/20220226120824/https://bleacherreport.com/articles/124676-2009-wwe-no-way-out-voices-and-chambers|url-status=live}}

In early 2009, The Undertaker began a second chapter to his unresolved feud with Shawn Michaels from the late 1990s, over a decade prior to this point (their tensions gradually increasing in the years immediately preceding this from heated run-ins at the 2007 and 2008 Royal Rumble matches). Their renewed feud by this point was two-dimensional, in part focusing on the wonder of The Undertaker's undefeated WrestleMania Streak in relation to, however, the fact that he had never before defeated Michaels in a singles match, only vice versa.{{cite news|last=Matthews|first=Graham|url=https://bleacherreport.com/articles/645529-wrestlemania-25-the-most-disappointing-wrestlemania-of-all-time|title=WrestleMania 25: The Most Disappointing WrestleMania of All Time|access-date=February 19, 2022|work=Bleacher Report|date=March 25, 2011|archive-date=March 9, 2023|archive-url=https://web.archive.org/web/20230309172401/https://bleacherreport.com/articles/645529-wrestlemania-25-the-most-disappointing-wrestlemania-of-all-time|url-status=live}} Michaels also made the buildup to their WrestleMania encounter personal, repeatedly demonstrating his Christian objections to the demonic dark side nature of The Undertaker's Deadman gimmick, even creating his own heaven-esque bright side spin-off of what he felt The Undertaker's gimmick should be (Michaels having become a real-life born again Christian by this point in his career).{{cite news |url=https://bleacherreport.com/articles/1558102-wrestlemania-classics-what-made-shawn-michaels-vs-undertaker-so-great |title=WrestleMania Classics: What Made Shawn Michaels vs. Undertaker so Great |access-date=February 25, 2022 |work=Bleacher Report |last=Dilbert |first=Ryan |date=March 8, 2013 |archive-date=March 9, 2023 |archive-url=https://web.archive.org/web/20230309172401/https://bleacherreport.com/articles/1558102-wrestlemania-classics-what-made-shawn-michaels-vs-undertaker-so-great |url-status=live }}{{cite news|url=https://bleacherreport.com/articles/2827831-how-triple-h-undertaker-shawn-michaels-crafted-epic-4-year-wrestlemania-saga|title=How Triple H, Undertaker, Shawn Michaels Crafted Epic 4-Year WrestleMania Saga|access-date=February 25, 2022|work=Bleacher Report|last=Wong|first=Kevin|date=April 4, 2019|archive-date=February 16, 2022|archive-url=https://web.archive.org/web/20220216073429/https://bleacherreport.com/articles/2827831-how-triple-h-undertaker-shawn-michaels-crafted-epic-4-year-wrestlemania-saga|url-status=live}} The feud culminated in a singles match between the two at WrestleMania 25 on April 5 in which Michaels made a heaven-sent entrance descending from up on high portraying his bright side anti-Deadman, while The Undertaker made a grave-risen entrance emerging from the ground.{{cite news|url=https://www.youtube.com/watch?v=VHvw3H8FueU|title=Shawn Michaels' 25th Anniversary of WrestleMania Entrance|access-date=February 25, 2022|work=WWE|archive-date=February 25, 2022|archive-url=https://web.archive.org/web/20220225071421/https://www.youtube.com/watch?v=VHvw3H8FueU|url-status=live}} After what was widely described as a suspenseful, competitive match, The Undertaker defeated Michaels, thus extending his WrestleMania winning streak to 17–0.{{cite web|url=http://www.wwe.com/shows/wrestlemania/25/matches/9074020|access-date=May 5, 2012|date=April 1, 2009|title=Undertaker def. Shawn Michaels|publisher=WWE|archive-date=February 1, 2022|archive-url=https://web.archive.org/web/20220201095410/https://www.wwe.com/shows/wrestlemania/25/matches/9074020|url-status=live}} Their encounter was highly acclaimed by critics and audiences alike and is considered by many to be one of the greatest WrestleMania matches of all time. On the April 24 episode of SmackDown, after losing a match against Big Show by knockout with Big Show taking advantage of The Undertaker's battered neck state from his previous WrestleMania encounter, The Undertaker attacked Big Show. Following this, The Undertaker took another hiatus from the WWE.{{cite news|url=https://www.wrestleview.com/wwe-smackdown-results/9965-smackdown-results-4-24-09/|title=Smackdown Results – 4/24/09|work=Wrestleview|access-date=February 26, 2022|last=Nemer|first=Paul|date=April 25, 2009|archive-date=February 26, 2022|archive-url=https://web.archive.org/web/20220226115921/https://www.wrestleview.com/wwe-smackdown-results/9965-smackdown-results-4-24-09/|url-status=live}}

After a four-month hiatus, The Undertaker returned at SummerSlam on August 23 by attacking CM Punk, who had just won the World Heavyweight Championship from Jeff Hardy in a Tables, Ladders, and Chairs match.{{cite web|url=http://www.wwe.com/shows/summerslam/history/2009/matches/hardypunk|access-date=May 5, 2012|date=August 23, 2009|title=CM Punk def. Jeff Hardy (New World Heavyweight Champion)|publisher=WWE|archive-date=April 3, 2022|archive-url=https://web.archive.org/web/20220403095929/https://www.wwe.com/shows/summerslam/history/2009/matches/hardypunk|url-status=live}} At Breaking Point on September 13, The Undertaker faced Punk in a submission match for the World Heavyweight Championship. The Undertaker had originally won the match with his Hell's Gate submission hold, but the match was restarted by SmackDown General Manager Theodore Long, who ruled that the ban placed on the move by Vickie Guerrero was still in effect. Punk went on to win the match with his anaconda vise when referee Scott Armstrong called for the bell, despite The Undertaker never submitting—a recreation of the Montreal Screwjob, which took place in the same venue in 1997.{{cite web|url=http://www.wwe.com/shows/wwebreakingpoint/matches/11460100/results/|access-date=September 26, 2009|date=September 13, 2009|last=Tello|first=Craig|title=Hell's Gate-crasher|publisher=WWE|url-status=dead|archive-url=https://web.archive.org/web/20090923191351/http://www.wwe.com/shows/wwebreakingpoint/matches/11460100/results/|archive-date=September 23, 2009}} On the September 25 episode of SmackDown, Theodore Long officially lifted the ban after being released from a casket that The Undertaker had him placed inside of, among a series of other horror-themed mind game tactics.{{cite web|url=http://slam.canoe.ca/Slam/Wrestling/2009/09/26/11135656.html|url-status=usurped |archive-url=https://archive.today/20120723213252/http://slam.canoe.ca/Slam/Wrestling/2009/09/26/11135656.html |archive-date=July 23, 2012|title=Smackdown: Punk escapes 'Taker's grasp|date=September 26, 2009|last=Sidhu|first=Manraj|access-date=May 5, 2012|work=Slam! Sports|publisher=Canadian Online Explorer}} With Long out of the way, the feud between The Undertaker and Punk pressed on and at Hell in a Cell on October 4, The Undertaker won the World Heavyweight Championship from him in a Hell in a Cell match.{{cite web|last1=Sokol|first1=Brian|last2=Sokol|first2=Chris|url=http://slam.canoe.com/Slam/Wrestling/PPVReports/2009/10/05/11300786.html|archive-url=https://web.archive.org/web/20150710194953/http://slam.canoe.com/Slam/Wrestling/PPVReports/2009/10/05/11300786.html|url-status=dead|archive-date=July 10, 2015|title=Title changes highlight Hell in a Cell|date=October 5, 2009|access-date=October 5, 2009|work=Slam Wrestling|publisher=Canadian Online Explorer}} The Undertaker successfully defended the title against CM Punk on the October 23 episode of SmackDown, in a fatal four-way match at Bragging Rights on October 25 against Punk, Batista and Rey Mysterio and in a triple threat match against Chris Jericho and Big Show at Survivor Series on November 22.{{cite web|url=http://slam.canoe.com/Slam/Wrestling/PPVReports/2009/10/25/11522721.html|archive-url=https://web.archive.org/web/20150706025436/http://slam.canoe.com/Slam/Wrestling/PPVReports/2009/10/25/11522721.html|url-status=dead|archive-date=July 6, 2015|title=Cena, Smackdown earn Bragging Rights|date=October 25, 2009|last=Bishop|first=Matt|access-date=February 1, 2010|work=Slam! Sports|publisher=Canadian Online Explorer}}{{cite web|url=http://slam.canoe.com/Slam/Wrestling/PPVReports/2009/11/23/11879686.html|archive-url=https://web.archive.org/web/20151018025201/http://slam.canoe.com/Slam/Wrestling/PPVReports/2009/11/23/11879686.html|url-status=dead|archive-date=October 18, 2015|title=Lots of wrestlers per match but no title changes at Survivor Series|date=November 23, 2009|last1=Plummer|first1=Dale|last2=Tylwalk|first2=Nick|access-date=February 1, 2010|work=Slam! Sports|publisher=Canadian Online Explorer}} He faced Batista at TLC: Tables, Ladders & Chairs on December 13 in a chairs match for the championship and won when the match was restarted by Long, after Batista had originally won after utilizing a low blow. The next night on Raw, The Undertaker competed in a tournament to crown the 2009 Superstar of the Year, losing to Randy Orton by countout in the first round after a distraction by Orton's protegès Cody Rhodes and Ted DiBiase.{{cite web|url=http://slam.canoe.com/Slam/Wrestling/PPVReports/2009/12/14/12146261.html|archive-url=https://web.archive.org/web/20151018112021/http://slam.canoe.com/Slam/Wrestling/PPVReports/2009/12/14/12146261.html|url-status=dead|archive-date=October 18, 2015|title=New champs at strong WWE TLC show|date=December 14, 2009|last=Kapur|first=Bob|access-date=February 1, 2010|work=Slam! Sports|publisher=Canadian Online Explorer}}

File:Undertaker prematch.jpg in January 2010]]

After successfully defending the World Heavyweight Championship against Rey Mysterio at the Royal Rumble on January 31, 2010,{{cite web|url=http://www.wwe.com/shows/royalrumble/matches/13224522/results/|title=Results: Under-World Title triumph|first=Michael|last=Burdick|date=January 31, 2010|publisher=WWE|access-date=February 1, 2010|archive-date=September 21, 2016|archive-url=https://web.archive.org/web/20160921042939/http://www.wwe.com/shows/royalrumble/matches/13224522/results/|url-status=live}} The Undertaker lost the championship at the Elimination Chamber pay-per-view on February 21. It was also at this event that a notorious shoot incident (non-kayfabe) befell The Undertaker: a pyrotechnics malfunction momentarily engulfed him in flames up to three times during his ring entrance. He was, however, able to continue with his scheduled match that night despite suffering first and second-degree burns on his chest and neck. According to a WWE spokesman, it "looked like a bad sunburn".{{cite web|url=http://www.aolnews.com/2010/02/22/the-undertaker-burned-during-accident-at-elimination-chamber/|title=The Undertaker Burned During Accident at Elimination Chamber|date=February 22, 2010|last=Fritz|first=Brian|access-date=June 25, 2014|publisher=AOL Fanhouse|url-status=dead|archive-url=https://web.archive.org/web/20140409065922/http://www.aolnews.com/2010/02/22/the-undertaker-burned-during-accident-at-elimination-chamber/|archive-date=April 9, 2014}} The Undertaker lost the title to Chris Jericho after interference from Shawn Michaels that night;{{cite web|url=http://slam.canoe.com/Slam/Wrestling/PPVReports/2010/02/22/12978356.html|archive-url=https://web.archive.org/web/20151018112021/http://slam.canoe.com/Slam/Wrestling/PPVReports/2010/02/22/12978356.html|url-status=dead|archive-date=October 18, 2015|title=Batista, Jericho and Michaels capitalize on Elimination Chamber opportunities|date=February 22, 2010|last1=Plummer|first1=Dale|last2=Tylwalk|first2=Nick|access-date=February 24, 2010|work=Slam! Sports|publisher=Canadian Online Explorer}} Jericho has said on multiple occasions that the pyrotechnician responsible for the accident was immediately escorted from the arena and relieved of his employment with WWE, following a threat of violence from Calaway.{{cite episode|title=Director/Actor Eli Roth|url=http://podcastone.com/Talk-Is-Jericho?showAllEpisodes=true|access-date=June 25, 2014|series=Talk is Jericho|network=PodcastOne|date=March 20, 2014|number=23|minutes=84|archive-date=March 24, 2014|archive-url=https://web.archive.org/web/20140324062829/http://podcastone.com/Talk-Is-Jericho?showAllEpisodes=true|url-status=live}}{{cite episode|title=WWE's Paul Heyman & Edge Pt 1|url=http://podcastone.com/Talk-Is-Jericho?showAllEpisodes=true|access-date=June 26, 2014|series=Talk is Jericho|network=PodcastOne|date=June 24, 2014|number=50|minutes=34|archive-date=March 24, 2014|archive-url=https://web.archive.org/web/20140324062829/http://podcastone.com/Talk-Is-Jericho?showAllEpisodes=true|url-status=live}} Calaway himself explained that he had previously expressed concerns to the technician regarding the pyro arrangement, but was ignored. He feels he was saved from severe injury by applying water to his hair, and altering his attire from a sleeveless to a sleeved jacket, just minutes before the accident.{{cite episode|title=One More Round: The Undertaker|series=Steve Austin's Broken Skull Sessions|network=WWE Network|date=November 22, 2020|minutes=83–92}}

The Undertaker then accepted Michaels's rematch offer, after initially declining, at WrestleMania XXVI on March 28 in a Streak vs. Career match, where The Undertaker was victorious and Shawn Michaels was forced to retire. This match also made both The Undertaker and Michaels the first men in WWE history to main event WrestleMania in three different decades (Undertaker main evented WrestleMania 13 and XXIV in 1997 and 2008 and Michaels main evented WrestleMania XII and XIV in 1996 and 1998 and XX and 23 in 2004 and 2007, respectively). After a hiatus (which included wrestling two matches on Raw), he returned to SmackDown on May 28, defeating Rey Mysterio to qualify for a spot at the Fatal 4-Way pay-per-view on June 20 to compete for the World Heavyweight title.{{cite web|url=http://www.wwe.com/shows/smackdown/archive/05282010|title=WWE "Back in black"|publisher=Wwe.com|access-date=October 24, 2011|archive-date=February 20, 2022|archive-url=https://web.archive.org/web/20220220101029/https://www.wwe.com/shows/smackdown/archive/05282010|url-status=live}} During the Rey Mysterio match, The Undertaker suffered a concussion, broken orbital bone and broken nose; he was visibly bleeding profusely on camera by the end of this match.{{cite web|url=http://wrestling.insidepulse.com/2010/05/31/undertaker-injured-wwe-fatal-4-way-main-event-in-jeopardy/|title=Inside Pulse Wrestling | Undertaker Injured, WWE Fatal 4 Way Main Event In Jeopardy|publisher=Wrestling.insidepulse.com|access-date=October 24, 2011|archive-date=April 13, 2014|archive-url=https://web.archive.org/web/20140413140446/http://wrestling.insidepulse.com/2010/05/31/undertaker-injured-wwe-fatal-4-way-main-event-in-jeopardy/|url-status=dead}} To cover for the injury, Kane revealed that The Undertaker had been found in a vegetative state on the June 4 episode of SmackDown;{{cite web|url=http://www.wwe.com/shows/smackdown/archive/06042010/mainarticle|title=WWE "Unnatural Phenom-enon"|publisher=Wwe.com|date=June 4, 2010|access-date=October 24, 2011|archive-date=February 20, 2022|archive-url=https://web.archive.org/web/20220220101026/https://www.wwe.com/shows/smackdown/archive/06042010/mainarticle|url-status=live}} Mysterio took his place in the match and won the World Heavyweight Championship. While attempting to learn which wrestler had attacked The Undertaker, Kane defeated Mysterio to win the World Heavyweight Championship at Money in the Bank. Kane and Mysterio continued to clash as they accused one another of being the assailant behind the mysterious ambush of The Undertaker.{{cite web|author=Brandon Stroud %BloggerTitle%|url=http://www.aolnews.com/2010/07/18/wwe-money-in-the-bank-2010-results-new-champion-cashes-in/|title=WWE Money in the Bank 2010 Results: New Champion Cashes In|publisher=Aolnews.com|date=July 18, 2010|access-date=October 24, 2011|archive-date=May 18, 2013|archive-url=https://web.archive.org/web/20130518165210/http://www.aolnews.com/2010/07/18/wwe-money-in-the-bank-2010-results-new-champion-cashes-in/|url-status=live}}

At SummerSlam on August 15, The Undertaker returned to confront Kane and Rey Mysterio, only to be attacked with a Tombstone Piledriver by Kane. With Kane revealed as his attacker, the two feuded for the next few months over the World Heavyweight Championship. After losing to Kane in a No Holds Barred match at Night of Champions on September 19, Paul Bearer returned as The Undertaker's manager on the September 24 episode of SmackDown.{{cite web|url=http://slam.canoe.com/Slam/Wrestling/2010/09/25/15475181.html|archive-url=https://web.archive.org/web/20160310041714/http://slam.canoe.com/Slam/Wrestling/2010/09/25/15475181.html|url-status=dead|archive-date=March 10, 2016|title=Smackdown: Kickin' it old school|date=September 25, 2010|last=Hillhouse|first=Dave|access-date=October 4, 2010|work=Slam! Sports|publisher=Canadian Online Explorer}} However, Bearer turned on him at Hell in a Cell on October 3 to help Kane win once again in a Hell in a Cell match. The feud ended at Bragging Rights on October 24 when The Nexus helped Kane defeat The Undertaker in a Buried Alive match (the half-brothers' final singles match against one another). The Undertaker needed surgery for a torn rotator cuff, causing him to be written off.{{Cite web|url=https://www.pwtorch.com/artman2/publish/WWE_News_3/article_44956.shtml|title=WWE News: Health updates on The Undertaker and C.M. Punk - both out for the rest of the year?|website=www.pwtorch.com|access-date=December 19, 2019|archive-date=April 21, 2022|archive-url=https://web.archive.org/web/20220421194433/https://www.pwtorch.com/artman2/publish/WWE_News_3/article_44956.shtml|url-status=live}}

{{Main|The Streak (professional wrestling)}}

After the 2011 Royal Rumble, promotional videos began airing, showing The Undertaker entering and standing within a Western-style, dilapidated shack on a rainy desert in Death Valley, The birthplace. Each promo ended with the date 2–21–11 being "burned into" the screen. On the February 21 episode of Raw, The Undertaker returned, but before he could speak, Triple H also returned and confronted him. The two challenged each other to a match at WrestleMania XXVII, which was later made a No Holds Barred match and which The Undertaker won by submission. However, he had to be carried away from the ring on a stretcher.{{cite web|url=http://www.wwe.com/shows/wrestlemania/27/triple-h-undertaker-streak-photos|title=Results:the Undertaker def. Triple H (No Holds Barred Match)|publisher=WWE|access-date=April 5, 2011|archive-date=February 4, 2012|archive-url=https://web.archive.org/web/20120204203237/http://www.wwe.com/shows/wrestlemania/27/triple-h-undertaker-streak-photos|url-status=live}} Following WrestleMania XXVII in 2011, The Undertaker would take on a more part-time role within the company; he would not have another match on Raw or SmackDown until 2013.

File:Wrestlemania 28 Undertaker vs HHH.jpg and The Undertaker at WrestleMania XXVIII]]

On the January 30, 2012 episode of Raw SuperShow, The Undertaker returned after a nine-month hiatus to confront Triple H.{{cite web|url=http://www.wwe.com/shows/raw/2012-01-30/results|title=The Undertaker returned with his sights set on Triple H|publisher=WWE|last=Passero|first=Mitch|date=January 30, 2012|access-date=January 30, 2012|archive-date=March 4, 2016|archive-url=https://web.archive.org/web/20160304043300/http://www.wwe.com/shows/raw/2012-01-30/results|url-status=live}} On the February 13 episode of Raw SuperShow, Triple H refused The Undertaker's challenge for a WrestleMania rematch.{{cite web|last=Medalis|first=Kara A.|title=WWE Raw SuperShow results: Has Cena embraced the hate?|url=http://www.wwe.com/shows/raw/2012-02-13/results|publisher=WWE|access-date=February 14, 2012|date=February 13, 2012|archive-date=March 4, 2016|archive-url=https://web.archive.org/web/20160304071908/http://www.wwe.com/shows/raw/2012-02-13/results|url-status=live}} After The Undertaker accused Triple H of living in the shadow of Shawn Michaels on the February 20 episode of Raw SuperShow, Triple H accepted the challenge on the condition that it would be a Hell in a Cell match; Michaels was later inserted as guest referee in the match. At WrestleMania XXVIII, The Undertaker, while debuting his new look, a mohawk, defeated Triple H to extend his Streak to 20–0. After the match, The Undertaker and Michaels carried Triple H to the entrance stage, where the three embraced.{{cite web|url=http://www.wwe.com/shows/wrestlemania/28/undertaker-triple-h-hell-in-a-cell|title=the Undertaker def. Triple H (Hell in a Cell Match with special referee Shawn Michaels)|publisher=WWE|access-date=March 2, 2013|archive-date=May 31, 2016|archive-url=https://web.archive.org/web/20160531015208/http://www.wwe.com/shows/wrestlemania/28/undertaker-triple-h-hell-in-a-cell|url-status=live}} Later in 2012, The Undertaker appeared on the 1000th episode of Raw on July 23 to help Kane, who had been confronted by Jinder Mahal, Curt Hawkins, Tyler Reks, Hunico, Camacho and Drew McIntyre. The Brothers of Destruction overcame and dominated the six other wrestlers.{{cite web|last=J.|first=Cyril|url=http://www.wwe.com/shows/raw/2012-07-23/raw-1000-results/page-9|title=Raw 1,000 results|work=WWE|access-date=July 23, 2012|archive-date=February 20, 2022|archive-url=https://web.archive.org/web/20220220103524/https://www.wwe.com/shows/raw/2012-07-23/raw-1000-results/page-9|url-status=live}}{{cite web|last=J.|first=Cyril|url=http://www.wwe.com/videos/undertaker-and-kane-fight-off-their-attackers-and-stand-tall-raw-july-23-2012-26039958|title=Undertaker and Kane fight off their attackers and stand tall: Raw, July 23, 2012|work=WWE|access-date=July 23, 2012|archive-date=July 24, 2012|archive-url=https://web.archive.org/web/20120724135254/http://www.wwe.com/videos/undertaker-and-kane-fight-off-their-attackers-and-stand-tall-raw-july-23-2012-26039958/|url-status=live}}

The Undertaker's next television appearance was on Old School Raw on March 4, 2013, where he opened the show by performing his signature entrance. CM Punk, Randy Orton, Big Show and Sheamus fought in a fatal four-way match to determine who would face him at WrestleMania 29, which Punk won.{{cite web|url=http://www.wwe.com/shows/raw/2013-03-04/wwe-raw-results-26096005|title=The Undertaker rises again and CM Punk punches his WrestleMania ticket|publisher=WWE.com|date=March 4, 2012|access-date=March 5, 2013|archive-date=February 20, 2022|archive-url=https://web.archive.org/web/20220220192043/https://www.wwe.com/shows/raw/2013-03-04/wwe-raw-results-26096005|url-status=live}} After the real-life death of Paul Bearer on March 5, 2013, a storyline involving Punk regularly spiting The Undertaker through displays of flippancy and disrespect towards Bearer's death began.{{cite web|url=http://www.wwe.com/videos/wwe-goes-into-overtime-raw-march-11-2013-26098254|title=WWE goes into overtime: Raw, March 11, 2013|publisher=WWE.com|date=March 11, 2013|access-date=March 20, 2013|archive-date=March 15, 2013|archive-url=https://web.archive.org/web/20130315045707/http://www.wwe.com/videos/wwe-goes-into-overtime-raw-march-11-2013-26098254|url-status=live}} Punk interrupted The Undertaker's ceremony to honor Bearer on Raw, stealing the trademark urn and later using it to attack Kane, humiliate The Brothers of Destruction and mock Bearer.{{cite web|url=http://www.wwe.com/videos/cm-punk-interrupts-undertakers-tribute-to-paul-bearer-raw-march-11-2013-26097992|title=CM Punk interrupts Undertaker's tribute to Paul Bearer: Raw, March 11, 2013|publisher=WWE.com|date=March 11, 2012|access-date=March 20, 2013|archive-date=March 15, 2013|archive-url=https://web.archive.org/web/20130315045447/http://www.wwe.com/videos/cm-punk-interrupts-undertakers-tribute-to-paul-bearer-raw-march-11-2013-26097992|url-status=dead}}{{cite web|url=http://www.wwe.com/videos/cm-punk-taunts-the-undertaker-with-paul-bearers-urn-raw-march-18-2013-26099706|title=CM Punk taunts the Undertaker with Paul Bearer's urn: RAW, March 18, 2013|publisher=WWE.com|date=March 18, 2012|access-date=March 20, 2013|archive-date=March 20, 2013|archive-url=https://web.archive.org/web/20130320102759/http://www.wwe.com/videos/cm-punk-taunts-the-undertaker-with-paul-bearers-urn-raw-march-18-2013-26099706|url-status=dead}} The Undertaker defeated Punk at WrestleMania 29 to extend his Streak to 21–0 and then took back the urn.{{cite web|url=http://www.wwe.com/shows/wrestlemania/29/wrestlemania-29-results-26104708|title=WrestleMania 29 results|work=WWE|access-date=April 8, 2013|archive-date=September 1, 2015|archive-url=https://web.archive.org/web/20150901050140/http://www.wwe.com/shows/wrestlemania/29/wrestlemania-29-results-26104708|url-status=live}} The following night on Raw, The Undertaker came out to pay his respects to Bearer, but was interrupted by The Shield, who attempted to attack Undertaker before Team Hell No (Kane and Daniel Bryan) made the save.{{Cite web|url=https://www.pwtorch.com/artman2/publish/wwerawreport/article_69884.shtml|title=PWTorch.com - CALDWELL'S WWE RAW RESULTS 4/8: Complete "virtual-time" coverage of live Raw - WM29 fall-out, new World Champ, no Rock, Taker live, crowd takes over|website=www.pwtorch.com|access-date=December 19, 2019|archive-date=April 3, 2019|archive-url=https://web.archive.org/web/20190403092537/https://www.pwtorch.com/artman2/publish/wwerawreport/article_69884.shtml|url-status=live}} The Undertaker would wrestle his final Raw match (his first since 2010) on the April 22 episode, teaming with Kane and Bryan against The Shield in a losing effort.{{Cite web|url=https://www.pwtorch.com/artman2/publish/wwerawreport/article_70166.shtml|title=PWTorch.com - CALDWELL'S WWE RAW RESULTS 4/22 (Second Hour): Shield vs. The Undertaker six-man tag match, Ryder squashed|website=www.pwtorch.com|access-date=December 19, 2019|archive-date=April 3, 2019|archive-url=https://web.archive.org/web/20190403010100/https://www.pwtorch.com/artman2/publish/wwerawreport/article_70166.shtml|url-status=live}} Four days later, he wrestled his final SmackDown match (also his first since 2010), defeating Shield member Dean Ambrose by submission. Afterward, The Undertaker was attacked by Ambrose and the rest of The Shield, who performed a triple powerbomb through the broadcast table on him.{{Cite web|url=https://www.pwtorch.com/artman2/publish/wwesmackdownreport/article_70252.shtml|title=PWTorch.com - PARKS' WWE SMACKDOWN REPORT 4/26: Complete coverage of the loaded Friday night show, including Undertaker vs. Ambrose, Henry vs. Orton|website=www.pwtorch.com|access-date=December 19, 2019|archive-date=November 16, 2018|archive-url=https://web.archive.org/web/20181116083307/https://www.pwtorch.com/artman2/publish/wwesmackdownreport/article_70252.shtml|url-status=live}}

File:The Undertaker WM30 entrance.jpg in 2014]]

On the February 24, 2014, episode of Raw, The Undertaker returned to confront Brock Lesnar and accepted his challenge for a match at WrestleMania XXX.{{cite web|last=Tylwalk|first=Nick|title=Raw: Longer matches and a dramatic return in Green Bay|url=http://slam.canoe.com/Slam/Wrestling/2014/02/25/21493241.html|archive-url=https://web.archive.org/web/20150710171552/http://slam.canoe.com/Slam/Wrestling/2014/02/25/21493241.html|url-status=dead|archive-date=July 10, 2015|work=SLAM! Wrestling|access-date=February 25, 2014}} After 25 minutes and three F-5s, Lesnar won the match at WrestleMania by pinfall, ending The Undertaker's Streak in what was described as "the most shocking result in WWE history".{{cite news|last=Murphy|first=Ryan|url=http://www.wwe.com/shows/wrestlemania/30/undertaker-brock-lesnar-26184576|title=Brock Lesnar def. The Undertaker|date=April 6, 2014|access-date=April 15, 2014|publisher=WWE|archive-date=March 2, 2014|archive-url=https://web.archive.org/web/20140302034323/http://www.wwe.com/shows/wrestlemania/30/undertaker-brock-lesnar-26184576|url-status=live}} Following the match, The Undertaker was hospitalized with a severe concussion which he suffered in the first minutes of the match.{{cite news|last=Butterly|first=Amelia|url=http://www.bbc.co.uk/newsbeat/26934095|title=WWE WrestleMania star The Undertaker has head injury|date=April 8, 2014|access-date=April 15, 2014|publisher=BBC|archive-date=February 28, 2015|archive-url=https://web.archive.org/web/20150228035845/http://www.bbc.co.uk/newsbeat/26934095|url-status=live}} In a December 2014 interview, Vince McMahon confirmed that it was his final decision to have Lesnar end The Streak and that The Undertaker was initially shocked at the decision. McMahon justified his decision that it would significantly enhance Lesnar's formidability to set up the next WrestleMania event and that there were no other viable candidates to fill Lesnar's role.{{cite web|title=WWE news: Austin/McMahon podcast – McMahon attempts to explain why Undertaker's Streak was broken at WM30|url=http://pwtorch.com/artman2/publish/WWE_News_3/article_82062.shtml|work=Pro Wrestling Torch|access-date=December 2, 2014|first=James|last=Caldwell|archive-date=December 12, 2014|archive-url=https://web.archive.org/web/20141212160740/http://pwtorch.com/artman2/publish/WWE_News_3/article_82062.shtml|url-status=live}} In 2014, The Undertaker was also offered to be inducted into the WWE Hall of Fame, but he declined the offer, feeling it wasn't time yet.{{cite news |last1=Ato |first1=Antonio Rubio |title=The Undertaker rechazó entrar al WWE Hall of Fame en 2014 |url=https://solowrestling.mundodeportivo.com/new/106981-the-undertaker-rechazo-entrar-al-wwe-hall-of-fame-en-2014- |access-date=March 24, 2022 |work=Solo Wrestling |date=March 17, 2022 |language=es |archive-date=March 24, 2022 |archive-url=https://web.archive.org/web/20220324104509/https://solowrestling.mundodeportivo.com/new/106981-the-undertaker-rechazo-entrar-al-wwe-hall-of-fame-en-2014- |url-status=live }}

File:Undertaker 2015 WrestleMania.jpg in 2015]]

In February 2015, Bray Wyatt began a series of cryptic promos which led to Fastlane, where Wyatt challenged The Undertaker to a match at WrestleMania 31, which The Undertaker accepted.{{cite web|url=http://pwtorch.com/artman2/publish/wweppvs/article_83486.shtml|title=CALDWELL'S WWE FAST LANE PPV RESULTS 2/22: Complete "virtual-time" coverage of Bryan vs. Reigns, Cena vs. Rusev, Sting-Hunter confrontation, final PPV before WM31|date=February 22, 2015|access-date=February 22, 2015|website=Pro Wrestling Torch|author=Caldwell, James|archive-date=March 30, 2019|archive-url=https://web.archive.org/web/20190330044633/https://www.pwtorch.com/artman2/publish/wweppvs/article_83486.shtml|url-status=live}}{{cite web|url=http://www.pwtorch.com/artman2/publish/wwerawreport/article_83746.shtml|title=CALDWELL'S WWE RAW RESULTS 3/9: Complete "virtual-time" coverage of live Raw – Lesnar appears, Orton strikes, Taker "responds" to Bray, Sting "speaks," latest WM31 hype, more|date=March 9, 2015|access-date=March 9, 2015|website=Pro Wrestling Torch|author=Caldwell, James|archive-date=March 13, 2015|archive-url=https://web.archive.org/web/20150313225639/http://pwtorch.com/artman2/publish/wwerawreport/article_83746.shtml|url-status=live}} At WrestleMania, The Undertaker defeated Wyatt after two Tombstone Piledrivers.{{cite web|url=http://pwtorch.com/artman2/publish/wweppvs/article_84175.shtml|title=CALDWELL'S WM31 PPV RESULTS 3/29: Complete "virtual-time" coverage of WWE World Title match, Taker's return, Sting vs. Triple H, Cena vs. Rusev, Rock/UFC surprise, more|date=March 29, 2015|access-date=March 29, 2015|website=Pro Wrestling Torch|author=Caldwell, James|archive-date=March 31, 2015|archive-url=https://web.archive.org/web/20150331225800/http://pwtorch.com/artman2/publish/wweppvs/article_84175.shtml|url-status=live}}

At Battleground in July, The Undertaker made his return by attacking Lesnar as he was on the verge of defeating Seth Rollins during his WWE World Heavyweight Championship match, causing the match to end in a disqualification win for Lesnar.{{cite web|url=http://pwtorch.com/artman2/publish/wweppvs/article_86322.shtml|title=CALDWELL'S WWE BATTLEGROUND PPV REPORT 7/19: Complete "virtual-time" coverage of live PPV – Rollins vs. Lesnar, Cena vs. Owens III, Orton returns home, more|date=July 19, 2015|access-date=July 19, 2015|website=Pro Wrestling Torch|last=Caldwell|first=James|archive-date=July 22, 2015|archive-url=https://web.archive.org/web/20150722175332/http://pwtorch.com/artman2/publish/wweppvs/article_86322.shtml|url-status=live}} The next night on Raw, The Undertaker explained his actions as revenge, not against Lesnar breaking The Streak, but rather the constant taunting he allowed Paul Heyman to engage in. Later that night, after The Undertaker and Lesnar brawled throughout the arena and had to be separated, a rematch was scheduled for SummerSlam in August, where The Undertaker controversially defeated Lesnar. Lesnar put The Undertaker in a kimura lock and the timekeeper rang the bell after seeing The Undertaker supposedly indicating submission, but since the referee had not seen a submission and never stopped the match, the match continued. The confusion allowed The Undertaker to surprise Lesnar with a low blow and apply Hell's Gate, in which Lesnar passed out.{{cite web|last1=Pappolla|first1=Ryan|title=The Undertaker def- Brock Lesnar|url=http://www.wwe.com/shows/summerslam/2015-undertaker-vs-brock-lesnar-27682861|publisher=WWE|access-date=July 20, 2015|archive-date=January 6, 2016|archive-url=https://web.archive.org/web/20160106004847/http://www.wwe.com/shows/summerslam/2015-undertaker-vs-brock-lesnar-27682861|url-status=live}} At Hell in a Cell, The Undertaker was defeated by Lesnar in a Hell in a Cell match after Lesnar hit him with his own low blow, returning the favor, and executing what was his third F-5 of the match.{{cite web|last1=Meltzer|first1=Dave|title=WWE Hell in a Cell live results: Brock Lesnar vs Undertaker, John Cena defends US Title (with updates on Alberto Del Rio)|url=http://www.f4wonline.com/wwe-news/wwe-hell-cell-live-results-brock-lesnar-vs-undertaker-john-cena-defends-us-title-updates|publisher=Wrestling Observer|access-date=December 21, 2015|date=October 26, 2015|archive-date=December 22, 2015|archive-url=https://web.archive.org/web/20151222122054/http://www.f4wonline.com/wwe-news/wwe-hell-cell-live-results-brock-lesnar-vs-undertaker-john-cena-defends-us-title-updates|url-status=live}}

While the crowd gave The Undertaker an ovation after his loss to Lesnar, he was attacked and captured by The Wyatt Family (Bray Wyatt, Luke Harper, Erick Rowan and Braun Strowman), who carried him away from the ring.{{cite web|last=Martin|first=Adam|url=http://www.wrestleview.com/wwe-hell-in-a-cell-2015/56660-wwe-hell-in-a-cell-ppv-results-10-25-15-live-from-los-angeles|title=WWE Hell in a Cell PPV Results|date=October 25, 2015|access-date=October 25, 2015|publisher=Wrestleview|archive-date=October 28, 2015|archive-url=https://web.archive.org/web/20151028232017/http://www.wrestleview.com/wwe-hell-in-a-cell-2015/56660-wwe-hell-in-a-cell-ppv-results-10-25-15-live-from-los-angeles|url-status=live}} After ambushing and capturing Kane the next night on Raw, Wyatt explained that he had claimed their souls and stole their demonic powers.{{cite web|last=Tedesco|first=Mike|url=http://www.wrestleview.com/wwe-wrestling-results/wwe-raw-results/56669-wwe-raw-results-10-26-15-live-results-from-san-dieg|title=WWE RAW Results – 10/26/15|date=October 26, 2015|access-date=October 26, 2015|publisher=Wrestleview|archive-date=November 17, 2015|archive-url=https://web.archive.org/web/20151117024603/http://www.wrestleview.com/wwe-wrestling-results/wwe-raw-results/56669-wwe-raw-results-10-26-15-live-results-from-san-dieg|url-status=live}} The Brothers of Destruction returned on the November 9 episode of Raw and attacked The Wyatt Family, setting up a tag team match at Survivor Series, which honored The Undertaker's 25 years in WWE.{{cite web|url=http://www.wwe.com/videos/the-undertaker-and-demon-kane-reemerge-to-unleash-hell-upon-the-wyatt-family-raw-28190849|title=The Undertaker and Demon Kane Return!|date=November 9, 2015|access-date=November 10, 2015|publisher=WWE.com|archive-date=November 12, 2015|archive-url=https://web.archive.org/web/20151112020148/http://www.wwe.com/videos/the-undertaker-and-demon-kane-reemerge-to-unleash-hell-upon-the-wyatt-family-raw-28190849|url-status=dead}} At Survivor Series on November 22, the Brothers of Destruction defeated Wyatt and Harper.{{cite web|url=http://www.wwe.com/shows/survivorseries/2015/undertaker-kane-wyatt-family-28201139|title=WWE Survivor Series 2015 Results: The Brothers of Destruction defeated The Wyatt Family|date=November 22, 2015|access-date=November 23, 2015|archive-date=June 9, 2017|archive-url=https://web.archive.org/web/20170609001401/http://www.wwe.com/shows/survivorseries/2015/undertaker-kane-wyatt-family-28201139|url-status=live}}

On the February 22, 2016, episode of Raw, Vince McMahon placed his son Shane McMahon, who returned to WWE for the first time since 2009, in a Hell in a Cell match at WrestleMania 32 against The Undertaker with the stipulation that if Shane won, he would gain control of Raw.{{cite web|last1=Caldwell|first1=James|title=2/22 Raw News|url=http://www.pwtorch.com/site/2016/02/22/vincesrawardfeb22/|website=PWTorch.com|access-date=April 22, 2016|date=February 23, 2016|archive-date=November 15, 2018|archive-url=https://web.archive.org/web/20181115112843/https://www.pwtorch.com/site/2016/02/22/vincesrawardfeb22/|url-status=live}} Vince later decided that should Undertaker lose the match against Shane, it would be his final match at WrestleMania.{{cite web|last1=Caldwell|first1=James|title=3/21 WWE Raw Results – Caldwell's Complete Live Report|url=http://www.pwtorch.com/site/2016/03/21/march21rawresults/|website=PWTorch.com|access-date=March 25, 2016|date=March 22, 2016|archive-date=October 6, 2016|archive-url=https://web.archive.org/web/20161006032515/http://www.pwtorch.com/site/2016/03/21/march21rawresults/|url-status=live}} After weeks of random physical confrontations and mind games exchanged between the pair, The Undertaker defeated Shane McMahon at WrestleMania 32.{{cite web|last1=Caldwell|first1=James|title=4/3 WrestleMania 32 PPV Results – CALDWELL'S Complete Live Report on Main PPV|url=http://www.pwtorch.com/site/2016/04/03/wm32liveresults/|publisher=Pro Wrestling Torch|access-date=April 3, 2016|archive-date=April 4, 2016|archive-url=https://web.archive.org/web/20160404040347/http://www.pwtorch.com/site/2016/04/03/wm32liveresults/|url-status=live}} The Undertaker would not appear again until the 900th episode of SmackDown on November 15, issuing a threat to Team SmackDown if they failed to defeat Team Raw at the upcoming Survivor Series pay-per-view.{{cite web|last=Martin|first=Adam|title=WWE Smackdown Results – 11/15/16 (Live from Wilkes-Barre, 900th episode, The Undertaker and Edge return)|url=http://www.wrestleview.com/wwe-wrestling-results/wwe-smackdown-results/69572-wwe-smackdown-results-111516-live-wilkes-barre-900th-episode-undertaker-edge-return/|work=WrestleView|access-date=November 15, 2016|date=November 15, 2016|archive-date=November 18, 2016|archive-url=https://web.archive.org/web/20161118232118/http://www.wrestleview.com/wwe-wrestling-results/wwe-smackdown-results/69572-wwe-smackdown-results-111516-live-wilkes-barre-900th-episode-undertaker-edge-return/|url-status=live}}

File:Taker-WM34.jpg

The Undertaker appeared on the January 23 episode of Raw, confronting Brock Lesnar and Goldberg.{{cite web|last1=Keller|first1=Wade|title=KELLER'S WWE RAW REPORT 1/23: Final show before the Royal Rumble, Goldberg-Lesnar hype, Reigns confronted by Jericho & Owens|url=http://www.pwtorch.com/site/2017/01/23/kellers-wwe-raw-report-123-final-show-royal-rumble-goldberg-lesnar-hype-reigns-confronted-jericho-owens/|website=pwtorch.com|publisher=TDH Communications Inc.|access-date=January 23, 2017|archive-date=February 2, 2017|archive-url=https://web.archive.org/web/20170202020110/http://www.pwtorch.com/site/2017/01/23/kellers-wwe-raw-report-123-final-show-royal-rumble-goldberg-lesnar-hype-reigns-confronted-jericho-owens/|url-status=live}} During the Royal Rumble on January 29, The Undertaker entered at number 29, eliminating Goldberg, The Miz, Baron Corbin and Sami Zayn, before being eliminated by the number 30 entrant, Roman Reigns.{{cite web|url=http://www.wwe.com/shows/royalrumble/article/2017-royal-rumble-statistics-entrants-eliminations|title=Full 2017 Royal Rumble Match statistics: entrants, eliminations, times and more|publisher=WWE.com|date=January 30, 2017|access-date=January 30, 2017|archive-date=July 15, 2017|archive-url=https://web.archive.org/web/20170715223049/http://www.wwe.com/shows/royalrumble/article/2017-royal-rumble-statistics-entrants-eliminations|url-status=live}} The Undertaker returned on the March 6 episode of Raw and performed a chokeslam on Reigns.{{cite web|last=Keller|first=Wade|title=KELLER'S WWE RAW REPORT 3/6: Fallout from Fastlane including Jericho asking Owens for explanation for breaking up their friendship|url=http://www.pwtorch.com/site/2017/03/06/kellers-wwe-raw-report-36-fallout-fastlane-including-jericho-asking-owens-explanation-breaking-friendship/|work=Pro Wrestling Torch|access-date=March 6, 2017|archive-date=March 7, 2017|archive-url=https://web.archive.org/web/20170307203904/http://www.pwtorch.com/site/2017/03/06/kellers-wwe-raw-report-36-fallout-fastlane-including-jericho-asking-owens-explanation-breaking-friendship/|url-status=live}} This led to a No Holds Barred match between The Undertaker and Reigns at WrestleMania 33,{{cite web|url=http://www.wwe.com/shows/wrestlemania/33/undertaker-vs-roman-reigns?sf62052304=1|title=The Undertaker vs. Roman Reigns|last=Clapp|first=John|date=March 13, 2017|work=WWE|access-date=March 13, 2017|archive-date=February 20, 2022|archive-url=https://web.archive.org/web/20220220112911/https://www.wwe.com/shows/wrestlemania/33/undertaker-vs-roman-reigns?sf62052304=1|url-status=live}} in which The Undertaker lost to Reigns after five spears in his fourth WrestleMania main event.{{cite web|url=http://www.wwe.com/shows/wrestlemania/33/undertaker-vs-roman-reigns-results|title=Roman Reigns def. The Undertaker|last=Burdick|first=Michael|work=WWE|access-date=April 2, 2017|archive-date=April 4, 2017|archive-url=https://web.archive.org/web/20170404043151/http://www.wwe.com/shows/wrestlemania/33/undertaker-vs-roman-reigns-results|url-status=live}} After the match, The Undertaker left his gloves, coat and hat in the center of the ring before slowly making his exit.{{cite web|last1=Powell|first1=Jason|title=Powell's WrestleMania 33 live review: Undertaker vs. Roman Reigns, Goldberg vs. Brock Lesnar for the WWE Universal Championship, AJ Styles vs. Shane McMahon, Seth Rollins vs. Triple H in an unsanctioned match|url=http://prowrestling.net/site/2017/04/02/powells-wrestlemania-33-live-review-undertaker-vs-roman-reigns-goldberg-vs-brock-lesnar-wwe-universal-championship-aj-styles-vs-shane-mcmahon-seth-rollins-vs-triple-h/|work=Pro Wrestling Dot Net|access-date=April 2, 2017|date=April 2, 2017|archive-date=April 3, 2017|archive-url=https://web.archive.org/web/20170403113529/http://prowrestling.net/site/2017/04/02/powells-wrestlemania-33-live-review-undertaker-vs-roman-reigns-goldberg-vs-brock-lesnar-wwe-universal-championship-aj-styles-vs-shane-mcmahon-seth-rollins-vs-triple-h/|url-status=live}}

The Undertaker took part in the Raw 25 Years broadcast on January 22, 2018, his first post-WrestleMania 33 appearance.{{Cite web |url=http://www.wwe.com/shows/raw/article/25th-anniversary-monday-night-raw-details |title=The 25th anniversary of Monday Night Raw will emanate from Barclays Center and Manhattan Center on Jan. 22 |date=October 30, 2017 |website=WWE |access-date=January 16, 2018 |archive-date=February 20, 2022 |archive-url=https://web.archive.org/web/20220220112912/https://www.wwe.com/shows/raw/article/25th-anniversary-monday-night-raw-details |url-status=live }} In the months prior to WrestleMania 34, John Cena challenged The Undertaker to a singles match. At WrestleMania, after Elias confronted Cena and was beaten down, The Undertaker's hat and coat appeared in the center of the ring and were struck by lightning. The Undertaker then appeared and beat Cena in a three-minute squash match.{{cite web|url=http://www.wrestleview.com/wwe-wrestlemania-results/101418-april-8-2018-brock-lesnar-roman-reigns/|title=WrestleMania 34 Results – 4/8/18 (Reigns vs. Lesnar, Styles vs. Nakamura, Rousey)|date=April 8, 2018|access-date=April 8, 2018|publisher=Wrestleview|archive-date=April 9, 2018|archive-url=https://web.archive.org/web/20180409171354/http://www.wrestleview.com/wwe-wrestlemania-results/101418-april-8-2018-brock-lesnar-roman-reigns/|url-status=live}} Three weeks later, The Undertaker defeated Rusev at WWE's Greatest Royal Rumble event in a casket match.{{cite web|last1=Burdick|first1=Michael|title=Undertaker vs. Rusev (Casket Match)|url=http://www.wwe.com/shows/greatest-royal-rumble/2018/undertaker-rusev|work=WWE|access-date=April 12, 2018|archive-date=February 20, 2022|archive-url=https://web.archive.org/web/20220220112921/https://www.wwe.com/shows/greatest-royal-rumble/2018/undertaker-rusev|url-status=live}} At Super Show-Down in Australia on October 6, The Undertaker faced Triple H in a no disqualification match billed as the "Last Time Ever"; they were accompanied by Kane and Shawn Michaels, respectively. The Undertaker lost the match after interference from Michaels. After the match, the four men shook hands as a sign of respect, however, The Undertaker and Kane would follow this by attacking them.{{cite web|last=Pappolla|first=Ryan|title=Triple H def. The Undertaker|url=https://www.wwe.com/shows/wwe-super-show-down/2018-10-06/the-undertaker-triple-h-results|publisher=WWE|access-date=October 6, 2018|archive-date=February 3, 2019|archive-url=https://web.archive.org/web/20190203145903/https://www.wwe.com/shows/wwe-super-show-down/2018-10-06/the-undertaker-triple-h-results|url-status=live}} As a result, the duos reunited their respective tag teams—the Brothers of Destruction and D-Generation X—and faced each other at Crown Jewel on November 2, where The Undertaker and Kane lost their final match as a tag team.{{cite web|last=Benigno|first=Anthony|title=D-Generation X def. The Brothers of Destruction|url=https://www.wwe.com/shows/wwe-crown-jewel/2018/triple-h-shawn-michaels-the-undertaker-kane-results|publisher=WWE|access-date=November 2, 2018|archive-date=November 3, 2018|archive-url=https://web.archive.org/web/20181103092331/https://www.wwe.com/shows/wwe-crown-jewel/2018/triple-h-shawn-michaels-the-undertaker-kane-results|url-status=live}}

On the April 8, 2019 episode of Raw, the night after WrestleMania 35—the first WrestleMania in 19 years without his involvement—The Undertaker appeared to interrupt and attack Elias during a musical performance.{{cite web|url=https://prowrestling.net/site/2019/04/08/4-8-powells-wwe-raw-tv-review-the-night-after-wrestlemania-35-edition-featuring-new-raw-and-smackdown-womens-champion-becky-lynch-new-wwe-universal-champion-seth-rollins-new-intercontinental-ch/|title=4/8 Powell's WWE Raw TV Review: The night after WrestleMania 35 edition featuring new Raw and Smackdown Women's Champion Becky Lynch, new WWE Universal Champion Seth Rollins, new Intercontinental Champion Finn Balor, and new Raw Tag Champions Zack Ryder and Curt Hawkins|date=April 8, 2019|last=Powell|first=Jason|work=Pro Wrestling Dot Net|access-date=April 9, 2019|archive-date=April 9, 2019|archive-url=https://web.archive.org/web/20190409081336/https://prowrestling.net/site/2019/04/08/4-8-powells-wwe-raw-tv-review-the-night-after-wrestlemania-35-edition-featuring-new-raw-and-smackdown-womens-champion-becky-lynch-new-wwe-universal-champion-seth-rollins-new-intercontinental-ch/|url-status=live}} The Undertaker made his return to the ring to face Goldberg at Super ShowDown in Saudi Arabia on June 7, defeating him in the main event of the night in their first match against each other.{{cite web|last=Powell|first=Jason|title=WWE Super ShowDown results: Powell's live review of Undertaker vs. Goldberg, Seth Rollins vs. Baron for the WWE Universal Championship, Kofi Kingston vs. Dolph Ziggler for the WWE Championship, Triple H vs. Randy Orton, Roman Reigns vs. Shane McMahon|url=https://prowrestling.net/site/2019/06/07/wwe-super-showdown-results-powells-live-review-of-undertaker-vs-goldberg-seth-rollins-vs-baron-for-the-wwe-universal-championship-kofi-kingston-vs-dolph-ziggler-for-the-wwe-championship-tripl/|work=Pro Wrestling Dot Net|access-date=June 7, 2019|date=June 7, 2019|archive-date=June 30, 2019|archive-url=https://web.archive.org/web/20190630060851/https://prowrestling.net/site/2019/06/07/wwe-super-showdown-results-powells-live-review-of-undertaker-vs-goldberg-seth-rollins-vs-baron-for-the-wwe-universal-championship-kofi-kingston-vs-dolph-ziggler-for-the-wwe-championship-tripl/|url-status=live}} On the June 24, 2019 episode of Raw, during a handicap match in which Roman Reigns was dominated by Shane McMahon and Drew McIntyre, The Undertaker suddenly appeared and attacked McMahon and McIntyre. The Undertaker and Reigns were later scheduled to face McMahon and McIntyre in a No Holds Barred tag team match at Extreme Rules. At Extreme Rules, The Undertaker and Reigns won. This turned out to be The Undertaker's final match in front of a live audience in the United States.{{cite web|url=https://prowrestling.net/site/2019/06/24/6-24-wwe-raw-results-powells-review-of-u-s-champion-ricochet-vs-aj-styles-in-a-non-title-match-roman-reigns-vs-shane-mcmahon-and-drew-mcintyre-in-a-handicap-match-wwe-champion-kofi-kingston-vs/|title=6/24 WWE Raw Results: Powell's review of U.S. Champion Ricochet vs. AJ Styles in a non-title match, Roman Reigns vs. Shane McMahon and Drew McIntyre in a handicap match, WWE Champion Kofi Kingston vs. Sami Zayn in a non-title match|date=June 24, 2019|last=Powell|first=Jason|work=Pro Wrestling Dot Net|access-date=June 25, 2019|archive-date=July 1, 2019|archive-url=https://web.archive.org/web/20190701031207/https://prowrestling.net/site/2019/06/24/6-24-wwe-raw-results-powells-review-of-u-s-champion-ricochet-vs-aj-styles-in-a-non-title-match-roman-reigns-vs-shane-mcmahon-and-drew-mcintyre-in-a-handicap-match-wwe-champion-kofi-kingston-vs/|url-status=live}}

The Undertaker returned at Super ShowDown in Saudi Arabia on February 27, 2020, as a surprise replacement in a gauntlet match. He entered the match last, replacing Rey Mysterio and defeating AJ Styles to win the Tuwaiq Mountain Trophy.{{cite web|title=The first-ever Tuwaiq Trophy Gauntlet Match|url=https://www.wwe.com/shows/wwe-super-showdown/wwe-super-showdown-2020/first-tuwaiq-trophy-match|work=WWE|date=February 11, 2020|access-date=February 11, 2020|archive-date=February 13, 2020|archive-url=https://web.archive.org/web/20200213220203/https://www.wwe.com/shows/wwe-super-showdown/wwe-super-showdown-2020/first-tuwaiq-trophy-match|url-status=live}} At Elimination Chamber during a match between Styles and Aleister Black, The Undertaker made another surprise appearance with an attack on Styles.{{cite news |last=Brookhouse |first=Brent |title=2020 WWE Elimination Chamber results, recap, grades: Shayna Baszler dominates, Undertaker appears |url=https://www.cbssports.com/wwe/news/2020-wwe-elimination-chamber-results-recap-grades-shayna-baszler-dominates-undertaker-appears/live/ |access-date=March 9, 2020 |work=CBSSports.com |date=March 9, 2020 |archive-date=March 9, 2020 |archive-url=https://web.archive.org/web/20200309054908/https://www.cbssports.com/wwe/news/2020-wwe-elimination-chamber-results-recap-grades-shayna-baszler-dominates-undertaker-appears/live/ |url-status=live }} The following night on Raw, Styles challenged The Undertaker to a match at WrestleMania 36.{{cite web|url=https://prowrestling.net/site/2020/03/09/3-9-wwe-raw-results-powells-review-of-edge-returning-following-randy-ortons-attack-on-beth-phoenix-rey-mysterio-vs-angel-garza-drew-mcintyre-in-action-the-build-to-wrestlemania-kicks-in/|title=3/9 WWE Raw Results: Powell's review of Edge returning following Randy Orton's attack on Beth Phoenix, Rey Mysterio vs. Angel Garza, Drew McIntyre in action, the build to WrestleMania kicks in|date=March 9, 2020|last=Powell|first=Jason|work=Pro Wrestling Dot Net|access-date=March 9, 2020|archive-date=March 20, 2020|archive-url=https://web.archive.org/web/20200320073605/https://prowrestling.net/site/2020/03/09/3-9-wwe-raw-results-powells-review-of-edge-returning-following-randy-ortons-attack-on-beth-phoenix-rey-mysterio-vs-angel-garza-drew-mcintyre-in-action-the-build-to-wrestlemania-kicks-in/|url-status=live}} Over the following weeks that led up to WrestleMania, a resentful Styles made unprecedented efforts to expose The Undertaker, going so far as departing from bashing his Deadman gimmick, instead taking to a metafiction form of bashing Calaway himself. The feud saw Styles solely referring to The Undertaker by his real name, Mark Calaway, referencing his age and his wife, Michelle McCool. In response, The Undertaker cut promos of ominous warning against Styles in which for the first time in years, he broke from the Deadman gimmick by presenting as himself out of character. In doing so, elements of his American Badass gimmick were reflected with Calaway making appearances in his biker gear. At WrestleMania 36, The Undertaker presented his third and final identity, "The Unholy Trinity", a combination of The Deadman, American Badass, and himself as Mark Calaway, this blend allowing him to trash talk Styles over real life matters during their encounter, while also able to maintain his superhuman horror capabilities.{{Cite web |last=Matadeen |first=Renaldo |url=https://www.cbr.com/wwes-the-last-ride-undertakers-unholy-trinity-boneyard-match/ |title=WWE's The Last Ride: How Undertaker's Unholy Trinity Made the Boneyard Match |date=June 26, 2020 |website=Comic Book Resources |access-date=April 20, 2021 |archive-date=April 25, 2021 |archive-url=https://web.archive.org/web/20210425093312/https://www.cbr.com/wwes-the-last-ride-undertakers-unholy-trinity-boneyard-match/ |url-status=live }} In what was subsequently learned to be The Undertaker's final match, he and Styles fought in a cemetery at a secluded rural locale, competing in what was a cinematic, narrative-heavy brawl similar to "Buried Alive matches",{{Cite web |url=http://www.wwe.com/inside/specialtymatches/buriedalivematch |title=Buried Alive matches |access-date=March 8, 2023 |archive-date=March 25, 2008 |archive-url=https://web.archive.org/web/20080325073927/http://www.wwe.com/inside/specialtymatches/buriedalivematch |url-status=dead }} named the "Boneyard match". Despite the assistance of Gallows and Anderson, The Undertaker buried Styles in the grave to win this match and ride off on motorcycle into the sunset,{{Cite web|url=https://bleacherreport.com/articles/2881953-the-undertaker-beats-aj-styles-in-boneyard-match-at-wwe-wrestlemania-36|title=The Undertaker Beats AJ Styles in Boneyard Match at WWE WrestleMania 36|last=Chiari|first=Mike|website=Bleacher Report|access-date=April 15, 2020|archive-date=October 26, 2020|archive-url=https://web.archive.org/web/20201026220634/https://bleacherreport.com/articles/2881953-the-undertaker-beats-aj-styles-in-boneyard-match-at-wwe-wrestlemania-36|url-status=live}} scoring his 25th WrestleMania victory to complete his professional wrestling career.{{cite news|url=https://www.cbr.com/wwe-undertaker-not-won-wrestlemania-match/|title=WWE: Undertaker May NOT Have Won His Last WrestleMania Match - Here's Why|access-date=February 26, 2022|work=Comic Book Resources|last=McCarrick|first=Michael|date=May 10, 2020|archive-date=February 27, 2022|archive-url=https://web.archive.org/web/20220227021844/https://www.cbr.com/wwe-undertaker-not-won-wrestlemania-match/|url-status=live}}

On June 21, 2020, in the final episode of the Undertaker: The Last Ride documentary, Callaway retired from the professional wrestling industry. Later on that November, he confirmed that he was "officially retired" in an interview. Many wrestlers and other public figures paid tribute to him on their social media pages.{{cite news |title=The Undertaker announces retirement; emotional fans, WWE Superstars pay tribute to 'Deadman' |url=https://www.wionews.com/sports/wwe-news-the-undertaker-announces-retirement-emotional-fans-wwe-superstars-pay-tribute-to-deadman-Undertaker-news-307609 |access-date=September 14, 2020 |work=WION |date=June 22, 2020 |archive-date=February 20, 2022 |archive-url=https://web.archive.org/web/20220220112910/https://www.wionews.com/sports/wwe-news-the-undertaker-announces-retirement-emotional-fans-wwe-superstars-pay-tribute-to-deadman-Undertaker-news-307609 |url-status=live }} Madison Square Garden, regarded as the most famous venue in professional wrestling, also paid tribute to him.{{cite news |last=Rego |first=Andrew |title=Undertaker Receives a Grand Tribute Following Retirement From WWE |url=https://www.essentiallysports.com/wwe-news-undertaker-receives-a-grand-tribute-following-retirement-from-wwe/ |access-date=September 14, 2020 |work=EssentiallySports |date=June 24, 2020 |archive-date=February 20, 2022 |archive-url=https://web.archive.org/web/20220220112911/https://www.essentiallysports.com/wwe-news-undertaker-receives-a-grand-tribute-following-retirement-from-wwe/ |url-status=live }}

Undertaker, wearing his trademark mortician trench coat and stetson hat, made an appearance at the conclusion of the Survivor Series event on November 22, 2020. The event is dedicated to him, commemorating thirty years from that time since his WWE debut. There, he reiterated that his career had been completed, giving an emotional farewell speech which ended in typical Undertaker fashion: "My time has come to let The Undertaker Rest in Peace."{{cite web|last=Powell|first=Jason|title=WWE Survivor Series results: Powell's review of Undertaker's Final Farewell, Drew McIntyre vs. Roman Reigns, Asuka vs. Sasha Banks, Kofi Kingston and Xavier Woods vs. The Street Profits, Bobby Lashley vs. Sami Zayn in champion vs. champion matches, Team Raw vs. Team Smackdown in Survivor Series elimination matches|url=https://prowrestling.net/site/2020/11/22/wwe-survivor-series-results-powells-review-of-undertakers-final-farewell-drew-mcintyre-vs-roman-reigns-asuka-vs-sasha-banks-kofi-kingston-and-xavier-woods-vs-the-street-profits-bobby-lashl/|website=Pro Wrestling Dot Net|date=November 22, 2020|access-date=November 22, 2020|archive-date=November 23, 2020|archive-url=https://web.archive.org/web/20201123000414/https://prowrestling.net/site/2020/11/22/wwe-survivor-series-results-powells-review-of-undertakers-final-farewell-drew-mcintyre-vs-roman-reigns-asuka-vs-sasha-banks-kofi-kingston-and-xavier-woods-vs-the-street-profits-bobby-lashl/|url-status=live}}{{cite web|url=https://www.essentiallysports.com/wwe-news-my-time-has-come-the-undertaker-gives-an-emotional-speech-on-his-final-farewell-at-survivor-series/|title=My Time has Come" – The Undertaker Gives an Emotional Speech on his Final Farewell at Survivor Series|first=Shuvangi Sen|last=Chaudhury|website=Essentially Sports|date=November 23, 2020|access-date=November 23, 2020|archive-date=February 20, 2022|archive-url=https://web.archive.org/web/20220220112908/https://www.essentiallysports.com/wwe-news-my-time-has-come-the-undertaker-gives-an-emotional-speech-on-his-final-farewell-at-survivor-series/|url-status=live}} A ten-bell salute was also given for The Undertaker character as he did his traditional take-the-knee pose, and a holographic image of Paul Bearer, Undertaker's former manager, was projected in the ring.{{cite news |last1=Brookhouse |first1=Brent |last2=Silverstein |first2=Adam |url=https://www.cbssports.com/wwe/news/2020-wwe-survivor-series-results-recap-grades-undertaker-bids-farewell-roman-reigns-drew-mcintyre-delivers/live/ |title=2020 WWE Survivor Series results, recap, grades: Undertaker bids farewell, Roman Reigns-Drew McIntyre delivers |work=CBS Sports |date=November 22, 2020 |access-date=November 23, 2020 |archive-date=November 30, 2020 |archive-url=https://web.archive.org/web/20201130223218/https://www.cbssports.com/wwe/news/2020-wwe-survivor-series-results-recap-grades-undertaker-bids-farewell-roman-reigns-drew-mcintyre-delivers/live/ |url-status=live }}

News that the Undertaker would be inducted into the WWE Hall of Fame class of 2022{{Cite web|title=The Undertaker to be inducted into the WWE Hall of Fame Class of 2022|url=https://www.wwe.com/shows/wwe-hall-of-fame/article/the-undertaker-to-be-inducted-into-the-wwe-hall-of-fame-class-of-2022|work=WWE|date=February 18, 2022|access-date=February 18, 2022|archive-date=February 20, 2022|archive-url=https://web.archive.org/web/20220220022645/https://www.wwe.com/shows/wwe-hall-of-fame/article/the-undertaker-to-be-inducted-into-the-wwe-hall-of-fame-class-of-2022/|url-status=live}} were responded to with extensive praise from WWE fans, the professional wrestling community and media outlets alike.{{cite news|url=https://www.cinemablend.com/television/ric-flair-shawn-michaels-kane-and-more-react-to-the-undertaker-making-the-wwe-hall-of-fame|title=Ric Flair, Shawn Michaels, Kane And More React To The Undertaker Making The WWE Hall Of Fame|access-date=February 11, 2022|work=CinemaBlend|last=Rawden|first=Mack|date=February 18, 2022|location=United States|archive-date=February 18, 2022|archive-url=https://web.archive.org/web/20220218193732/https://www.cinemablend.com/television/ric-flair-shawn-michaels-kane-and-more-react-to-the-undertaker-making-the-wwe-hall-of-fame|url-status=live}} On March 3, 2022, on The Pat McAfee Show, WWE Chairman Vince McMahon stated that he would be Undertaker's WWE Hall of Fame inductor. In praising Undertaker both inside and outside of character in a heartfelt message, McMahon said that the induction would be one of the most difficult endeavors of his life because of his longtime history with Undertaker, and how close they were behind the scenes.{{cite magazine|url=https://www.si.com/wrestling/2022/03/03/vince-mcmahon-induct-the-undertaker-wwe-hall-of-fame-pat-mcafee-interview|title=Vince McMahon To Induct The Undertaker Into WWE Hall of Fame|access-date=March 4, 2022|magazine=Sports Illustrated|last=Scott|first=Jelani|date=March 3, 2022|archive-date=March 4, 2022|archive-url=https://web.archive.org/web/20220304013109/https://www.si.com/wrestling/2022/03/03/vince-mcmahon-induct-the-undertaker-wwe-hall-of-fame-pat-mcafee-interview|url-status=live}} Undertaker issued a Twitter response later on that same day, which read:

{{blockquote|After over 30 years of long roads traveled, countless hours of TV, and one hell of a ride together… couldn't think of anyone better to put me in the #WWEHOF than @VinceMcMahon. One final ride together, old-timer!!!{{cite news|url=https://thespun.com/more/wrestling/look-the-undertaker-reacts-to-vince-mcmahons-announcement|title=Look: The Undertaker Reacts To Vince McMahon's Announcement|work=The Spun|accessdate=March 4, 2022|last=Machlin|first=Tzvi|date=March 3, 2022|archive-date=February 12, 2024|archive-url=https://web.archive.org/web/20240212181106/https://thespun.com/more/wrestling/look-the-undertaker-reacts-to-vince-mcmahons-announcement|url-status=live}}| The Undertaker}}On April 1, 2022, The Undertaker was formally inducted into the WWE Hall of Fame at the American Airlines Center.{{Cite news |first=Marc |last=Middleton |date=April 2, 2022 |title=Noelle Foley On The Undertaker Not Mentioning Her Dad In His WWE HOF Speech, Taker Gives Thanks |url=https://www.wrestlinginc.com/news/2022/04/noelle-foley-on-the-undertaker-not-mentioning-her-dad-in-his-wwe-hof-speech-taker-gives-thanks/ |access-date=April 2, 2022 |work=Wrestling Inc. |archive-date=April 2, 2022 |archive-url=https://web.archive.org/web/20220402154746/https://www.wrestlinginc.com/news/2022/04/noelle-foley-on-the-undertaker-not-mentioning-her-dad-in-his-wwe-hof-speech-taker-gives-thanks/ |url-status=live }} At his induction, Calaway made a 137-minute speech that opened with a 10-minute, emotional standing ovation from the live audience, bringing Calaway to tears. Calaway's acceptance speech, hailed by media outlets as matchless and beyond compare, was motivational and shared his collection of self-reflections and life philosophies for success. In making his speech, he stood before several genres of his Deadman character, through the varying costumes displayed on mannequins.{{Cite news |title=The Undertaker in tears: Watch his viral emotional speech during WWE Hall of Fame induction |url=https://www.dnaindia.com/sports/report-the-undertaker-in-tears-watch-his-viral-emotional-speech-during-wwe-hall-of-fame-induction-2943741 |work=DNA |date=April 2, 2022 |access-date=April 3, 2022 |archive-date=February 3, 2023 |archive-url=https://web.archive.org/web/20230203094540/https://www.dnaindia.com/sports/report-the-undertaker-in-tears-watch-his-viral-emotional-speech-during-wwe-hall-of-fame-induction-2943741 |url-status=live }} Later that same weekend, Calaway made appearances on the entrance stage on both nights of WrestleMania.

File:The Rock and Undertaker, WrestleMania XL.jpg at WrestleMania XL.]]

On January 23, 2023, The Undertaker made an appearance at the Monday Night Raw 30th Anniversary special, Raw is XXX. He appeared under his American Badass gimmick, confronting LA Knight and seemingly giving his approval to Bray Wyatt.{{Cite news |last=Ravens |first=Andrew |title=Bray Wyatt on WWE Raw 30 segment with The Undertaker: 'This moment justified a lifetime of sacrifices for me' |url=https://wrestlingnews.co/wwe-news/bray-wyatt-on-wwe-raw-30-segment-with-the-undertaker-this-moment-justified-a-lifetime-of-sacrifices-for-me |access-date=January 27, 2023 |newspaper=Wrestling News | Wwe and Aew Results, Spoilers, Rumors & Scoops |language=en |archive-date=January 27, 2023 |archive-url=https://web.archive.org/web/20230127124025/https://wrestlingnews.co/wwe-news/bray-wyatt-on-wwe-raw-30-segment-with-the-undertaker-this-moment-justified-a-lifetime-of-sacrifices-for-me |url-status=live }} On October 10, 2023, The Undertaker made his first appearance on WWE NXT chokeslamming Bron Breakker.{{Cite news |last=Rose |first=Bryan |date=October 11, 2023 |title=The Undertaker lays out Bron Breakker on WWE NXT |url=https://www.f4wonline.com/news/nxt/the-undertaker-lays-out-bron-breakker-on-wwe-nxt |work=F4W Online |access-date=October 11, 2023 |archive-date=October 12, 2023 |archive-url=https://web.archive.org/web/20231012031037/https://www.f4wonline.com/news/nxt/the-undertaker-lays-out-bron-breakker-on-wwe-nxt |url-status=live }}

On April 5, 2024, The Undertaker inducted Muhammad Ali into the 2024 WWE Hall of Fame.{{cite web|url=https://www.youtube.com/watch?v=tKK2UGSxmSM|title=The Undertaker inducts Muhammad Ali into the WWE Hall of Fame: 2024 WWE Hall of Fame highlights|date=April 5, 2024|work=WWE YouTube|access-date=April 5, 2024}} On April 7, 2024, The Undertaker appeared briefly during the Night 2 main event of WrestleMania XL between Roman Reigns and Cody Rhodes where he aided Cody Rhodes and chokeslammed The Rock.{{Cite news |last=Rathi |first=Ishaan |date=April 8, 2024 |title=Cody Rhodes Wins Undisputed WWE Championship In Match Filled with Surprises at WrestleMania 40 Sunday |url=https://www.ringsidenews.com/2024/04/07/cody-rhodes-wins-undisputed-wwe-championship-in-match-filled-with-surprises-at-wrestlemania-40-sunday/ |work=Ringside News |access-date=April 8, 2024}} On the Raw premiere on Netflix on January 6, 2025, The Undertaker made an appearance under his American Badass persona and congratulated the new Women's World Champion Rhea Ripley after her victory.{{Cite web |last=Beaston |first=Erik |title=WWE Raw on Netflix Debut Results: Winners, Live Grades, Reaction and Highlights |url=https://bleacherreport.com/articles/10149884-wwe-raw-on-netflix-debut-results-winners-live-grades-reaction-and-highlights |access-date=January 7, 2025 |website=Bleacher Report |language=en}}

File:Undertaker rey de las sombras.jpg

Under his undead, funereal, and macabre horror-themed gimmick, in which The Undertaker is subtitled "The Deadman", he routinely took to alarmist tactics to disrupt the focus and confidence of his rivals.{{cite news |url=https://books.google.com/books?id=SJkOBAAAQBAJ&dq=the+undertaker+undead+wwf&pg=PA101 |title=The Complete WWF Video Guide Volume 2 (p. 101) |access-date=January 31, 2022 |last=Dixon |first=James |date=January 1, 2012 |publisher=Lulu.com |isbn=9781291252927 |archive-date=July 16, 2023 |archive-url=https://web.archive.org/web/20230716003435/https://books.google.com/books?id=SJkOBAAAQBAJ&dq=the+undertaker+undead+wwf&pg=PA101 |url-status=live }} Often, these alarmist tactics were morbid and applied the use of props that reflected demise as the consequence of a wrestling match against him: caskets (sometimes personalizing casket designs to represent his opponents),{{cite news|url=https://www.smarkoutmoment.com/2018/04/wrestling-history-lessons-undertakers.html|title=Wrestling History Lessons: The Undertaker's Casket Matches|access-date=February 22, 2022|work=Smark Out Moment|last=Maldonado|first=Jonathan|date=April 26, 2018|archive-date=February 22, 2022|archive-url=https://web.archive.org/web/20220222093833/https://www.smarkoutmoment.com/2018/04/wrestling-history-lessons-undertakers.html|url-status=live}} body bags,{{cite news|url=https://books.google.com/books?id=hMhbAgAAQBAJ&dq=undertaker+body+bag&pg=PT15|title=Pro Wrestling Legends: The Undertaker|access-date=January 31, 2022|work=Info Base Learning|last=Ross|first=Dan|date=January 1, 2013|isbn=9781438146553|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003418/https://books.google.com/books?id=hMhbAgAAQBAJ&dq=undertaker+body+bag&pg=PT15|url-status=live}} corpse-like effigies,{{cite news|url=https://bloody-disgusting.com/news/3425352/wrestlings-scariest-moments-diesel-finds-body-undertakers-casket/|title=Wrestling's Scariest Moments: Diesel Finds His Own Body in Undertaker's Casket|access-date=January 31, 2022|work=Bloody Disgusting|last=Squires|first=John|date=February 20, 2017|archive-date=January 31, 2022|archive-url=https://web.archive.org/web/20220131170335/https://bloody-disgusting.com/news/3425352/wrestlings-scariest-moments-diesel-finds-body-undertakers-casket/|url-status=live}} cemeteries, hearses.{{cite news|url=https://books.google.com/books?id=seQsEAAAQBAJ&dq=The+Undertaker+moveset&pg=PA171|title=America Under Construction: Boundaries and Identities in Popculture (p. 172)|access-date=January 28, 2022|work=America Under Construction|last1=Long|first1=Kristi|last2=Nadelhaft|first2=Matthew|date=January 1, 2017|isbn=9781315459967|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003418/https://books.google.com/books?id=seQsEAAAQBAJ&dq=The+Undertaker+moveset&pg=PA171|url-status=live}} To that end, the gimmick evoked funerals and death down to finer details, such as in the character's birthplace of Death Valley, catchphrase of "Rest in Peace", signature finishing maneuver of the Tombstone Piledriver, a wrestling pin that had the opponent resemble a corpse with their arms crossed over their chest, etc.{{cite news|url=https://www.espn.com/wwe/story/_/id/17167514/wwe-undertaker-accolades-stats-information|title=WWE Profile - The Undertaker|access-date=January 1, 2022|work=ESPN|last=Hillabi|first=Amer|date=August 11, 2016|archive-date=January 1, 2022|archive-url=https://web.archive.org/web/20220101104851/https://www.espn.com/wwe/story/_/id/17167514/wwe-undertaker-accolades-stats-information|url-status=live}} Adding to his many effects of treating his wrestling matches as funeral services, The Undertaker frequently served a list of specialized matches that were personalized to his Deadman gimmick: Casket Match, Body Bag Match, Buried Alive Match, Last Ride Match, Hell in a Cell, Boneyard Match, etc.{{cite news|url=https://www.wrestling-world.com/news/news/wwe/6316/the-undertaker-says-thank-you-to-the-fans/|title=The Undertaker says 'Thank you' to the fans|access-date=January 30, 2022|work=WrestlingWorld|last=Brugnoli|first=Simone|date=June 27, 2020|archive-date=January 30, 2022|archive-url=https://web.archive.org/web/20220130124619/https://www.wrestling-world.com/news/news/wwe/6316/the-undertaker-says-thank-you-to-the-fans/|url-status=live}}{{cite news|url=https://books.google.com/books?id=OHa5BAAAQBAJ&dq=last+ride+match+undertaker&pg=PP9|title=101 Things You May Not Have Known About World Wrestling|access-date=January 30, 2022|work=Apex Publishing|last=White|first=Paul|date=January 1, 2012|isbn=9781908752857|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003455/https://books.google.com/books?id=OHa5BAAAQBAJ&dq=last+ride+match+undertaker&pg=PP9|url-status=live}}{{cite news|url=https://books.google.com/books?id=DcKMDwAAQBAJ&dq=casket+match+undertaker&pg=PR11|title=Mayor Kane: My Life in wrestling and Politics|access-date=January 30, 2022|work=Center Street|last=Jacobs|first=Glenn|date=November 1, 2019|isbn=9781546085829|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003426/https://books.google.com/books?id=DcKMDwAAQBAJ&dq=casket+match+undertaker&pg=PR11|url-status=live}}

Filled with bells and whistles, The Undertaker's godlike superhuman presence and indignation were signaled by funeral tolls, settings of pitch-black darkness and blue/purple semidarkness, flickering lights, hazy fog, thunder, lightning strikes, and other bone-chilling scenes and sound activity.{{cite news|url=https://bleacherreport.com/articles/1625261-undertakers-7-best-entrances-of-all-time|title=The Undertaker's 7 Best Entrances of All Time|access-date=January 1, 2022|work=CBSlocal|last=Dilbert|first=Ryan|date=May 1, 2013|archive-date=January 18, 2022|archive-url=https://web.archive.org/web/20220118182511/https://bleacherreport.com/articles/1625261-undertakers-7-best-entrances-of-all-time|url-status=live}}{{cite news|url=https://pittsburgh.cbslocal.com/2017/01/12/who-will-be-undertakers-opponent-at-wrestlemania/|title=Who Will Be Undertaker's Opponent At WrestleMania?|access-date=January 1, 2022|work=CBSlocal|last=Carroll|first=Chuck|date=January 12, 2017|archive-date=January 1, 2022|archive-url=https://web.archive.org/web/20220101104852/https://pittsburgh.cbslocal.com/2017/01/12/who-will-be-undertakers-opponent-at-wrestlemania/|url-status=live}}{{cite news|url=https://prowrestling.net/artman/publish/pruettblog/article10036636.shtml|title=Pruett's Blog Flashback: The Undertaker's Streak Series Part Three - The American Bad Ass Years & The Deadman's Return - WrestleMania XVII - WrestleMania XX|access-date=January 1, 2022|work=Prowrestling.net|last=Pruett|first=Will|date=April 2, 2014|archive-date=January 1, 2022|archive-url=https://web.archive.org/web/20220101105020/https://prowrestling.net/artman/publish/pruettblog/article10036636.shtml|url-status=live}} Portrayed as miraculously resilient to destruction,{{cite news|url=https://books.google.com/books?id=_tCGDwAAQBAJ&q=could%20bounce%20back%20from%20any%20form%20of%20punishment%20The%20Undertaker|title=Pro Wrestling FAQ: All That's Left To Know About The World's Most Entertaining Spectacle|access-date=February 11, 2022|work=Backbeat Books|last=Solomon|first=Brian|date=January 1, 2015|isbn=9781617136283|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003443/https://books.google.com/books?id=_tCGDwAAQBAJ&q=could%20bounce%20back%20from%20any%20form%20of%20punishment%20The%20Undertaker|url-status=live}} The Undertaker yielded numerous resurrections, which sometimes gave way to reincarnations of his Deadman gimmick. While maintaining his general character premise as death personified with accompanying alarmist tactics throughout all sagas of the Deadman,{{cite news|url=https://books.google.com/books?id=seQsEAAAQBAJ&dq=death+personified+the+undertaker&pg=PA171|title=America Under Construction|access-date=January 23, 2022|work=Routledge|last1=Long|first1=Kristi|last2=Nadelhaft|first2=Matthew|date=January 1, 2017|isbn=9781315459967|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003446/https://books.google.com/books?id=seQsEAAAQBAJ&dq=death+personified+the+undertaker&pg=PA171|url-status=live}}{{cite news|url=https://bleacherreport.com/articles/2408442-the-undertaker-vs-bray-wyatt-keeping-deadman-off-tv-makes-match-more-effective|title=The Undertaker vs. Bray Wyatt: Keeping Deadman off TV Makes Match More Effective|access-date=January 31, 2022|work=Bleacher Report|last=Konuwa|first=Alfred|date=March 25, 2015|archive-date=January 31, 2022|archive-url=https://web.archive.org/web/20220131165617/https://bleacherreport.com/articles/2408442-the-undertaker-vs-bray-wyatt-keeping-deadman-off-tv-makes-match-more-effective|url-status=live}} each incarnation took on its own distinct appearance and characterization. For example, some Deadman incarnations were unearthly and zombie-like while others were Goth and comparatively more human.{{cite news|url=https://slamwrestling.net/index.php/1998/08/01/undertaker-likes-his-new-attitude/|title=UNDERTAKER LIKES HIS NEW ATTITUDE|access-date=January 1, 2022|work=Slamwrestling|last=Powell|first=John|date=August 1, 1998|archive-date=January 1, 2022|archive-url=https://web.archive.org/web/20220101110021/https://slamwrestling.net/index.php/1998/08/01/undertaker-likes-his-new-attitude/|url-status=live}}

The earliest of The Undertaker's Deadman incarnations (nicknamed in external media as "The Old West Mortician" to distinguish from his other Deadman incarnations) depicted him as a menacing derivative of the Wild West undertakers in television westerns. In his own rendition, he was garbed in a black trench coat; gray-striped tie; black-ribboned, black stetson; gray boot spats; and gray gloves{{cite news|url=https://books.google.com/books?id=KUsJAwAAQBAJ&dq=the+undertaker+gray+boot+spats+gray+gloves&pg=PA306|title=Historical Dictionary of Wrestling - Page 306|access-date=February 23, 2022|work=The Scarecrow Press|last=Grasso|first=John|date=March 6, 2014|isbn=9780810879263|archive-date=July 16, 2023|archive-url=https://web.archive.org/web/20230716003438/https://books.google.com/books?id=KUsJAwAAQBAJ&dq=the+undertaker+gray+boot+spats+gray+gloves&pg=PA306|url-status=live}} (black gloves for first few appearances before gray).{{cite news|url=https://bleacherreport.com/articles/2548866-undertakers-early-career-a-reminder-of-how-vital-finding-the-right-gimmick-is|title=Undertaker's Early Career a Reminder of How Vital Finding the Right Gimmick Is|access-date=February 27, 2022|work=Bleacher Report|last=Dilbert|first=Ryan|date=August 20, 2015|archive-date=September 10, 2021|archive-url=https://web.archive.org/web/20210910220059/https://bleacherreport.com/articles/2548866-undertakers-early-career-a-reminder-of-how-vital-finding-the-right-gimmick-is|url-status=live}} However, most of The Undertaker's Deadman character development (sleeve tattoos, longer/straightened/black hair, purple/blue color representation, elements of thunder and lightning, etc.) would not surface until his first reincarnation into what was his rebirthed Deadman variation, lasting from SummerSlam 94' (resurrection from a death angle with Yokozuna) through Buried Alive: In Your House (The Undertaker buried alive by Mankind and numerous other WWF heel wrestlers). In these initial zombie-like incarnations of his gimmick, he was portrayed as impervious to pain, something accomplished by Calaway not selling his opponents' attacks. Among the many ways this was showcased was The Undertaker's maneuver of raising up from a taken down supine position into a high Fowler's position, dubbed "the sit-up" (often accompanied by his sharp hissing sound).

Beginning early on, The Undertaker's persona was complemented with histrionically spooky, wailing manager Paul Bearer, introduced to represent and guide The Deadman.{{cite news|url=https://www.youtube.com/watch?v=mLJ2KbG_BeI|title=The Undertaker vs. British Bulldog – WWE Championship Match: Nov. 30, 1991|work=WWE YouTube|date=November 7, 2020|access-date=March 6, 2022|archive-date=March 6, 2022|archive-url=https://web.archive.org/web/20220306021132/https://www.youtube.com/watch?v=mLJ2KbG_BeI&gl=US&hl=en|url-status=live}} Playing a key role, Bearer used an urn to transmit mysterious powers to The Undertaker that had supernatural healing effects on him during combat.{{cite web |last=Yardley |first=WIiliam |url=https://www.nytimes.com/2013/03/12/arts/television/william-moody-58-pro-wrestlings-paul-bearer-dies.html |title=William Moody, 58, Pro Wrestling's Paul Bearer, Dies |date=March 11, 2013 |access-date=April 20, 2021 |work=The New York Times |archive-date=April 20, 2021 |archive-url=https://web.archive.org/web/20210420151736/https://www.nytimes.com/2013/03/12/arts/television/william-moody-58-pro-wrestlings-paul-bearer-dies.html |url-status=live }} Also linked to The Undertaker's Deadman gimmick were the druids–a team of mysterious, incognito cult-like members, completely disguised in black hooded clergy robes.{{cite news|url=https://books.google.com/books?id=qriHDwAAQBAJ&dq=the+undertaker%27s+druids++like+wwe&pg=PT341|title=WWE Smack Down 20 years and counting|access-date=January 29, 2022|work=DK Publishing|last1=Jones|first1=John|last2=Vazquez|first2=Sara|date=January 1, 2019|isbn=978-1-4654-8706-3 }} A mysterious choir chanting sounded whenever the druids presented.{{cite news|url=https://books.google.com/books?id=2geXCwAAQBAJ&dq=the+undertaker+druids+theme&pg=PA137|title=The Raw Files 2015|access-date=January 29, 2022|last1=Dixon|first1=James|last2=Furious|first2=Arnold|last3=Rick|first3=Ashley|last4=Dahlstrom|first4=Bob|date=January 1, 2016|publisher=Lulu.com |isbn=978-1-326-52984-0 }} The druids typically appeared for the purposes of removing The Undertaker where he had seemingly been extinguished by his enemies (as opposed to EMTs or medical personnel used for the rest of WWF/E talent). The druids were also seen reproducing The Undertaker in recovered, wrathful states to those same enemies who were thought to have extinguished him.{{cite news|url=https://books.google.com/books?id=PS0IBAAAQBAJ&dq=the+undertaker+druids+return&pg=PA149|title=30 Years of WrestleMania|access-date=January 16, 2022|work=Thirty Years of WrestleMania|last1=Shields|first1=Brian|last2=Miller|first2=Dean|date=September 15, 2014 |isbn=978-1-4654-3420-3 }}

The Undertaker took to many trademarked idiosyncrasies and themes, including a stylized throat-slashing gesture,{{cite news|url=https://books.google.com/books?id=Up5-DwAAQBAJ&dq=throat+slashing+gesture+the+undertaker&pg=PA125|title=WWE Greatest Rivalries|access-date=February 3, 2022|work=Penguin Random House|last=Afram|first=Pamela|date=January 1, 2019|isbn=978-1-4654-8634-9 }} grimacing facial expressions fit with eyeballs rolled back so that only the whites of his eyes displayed,{{cite news|url=https://books.google.com/books?id=IPcwDQAAQBAJ&dq=WWE+Undertaker+eyes+rolled&pg=PT178|title=America Under Construction: Boundaries and Identities in Popculture|access-date=January 28, 2022|work=America Under Construction|last1=Long|first1=Kristi|last2=Nadelhaft|first2=Matthew|date=January 1, 2017|isbn=978-1-315-51187-0 }} backwards hair-whips so as to expose his ominous facial expressions,{{cite news|url=https://www.forbes.com/sites/alfredkonuwa/2018/04/07/wwe-wrestlemania-34-the-undertaker-vs-the-american-badass-a-tale-of-the-tape/?sh=3841f2dd2847|title=WWE WrestleMania 34: The Undertaker Vs. The American Badass, A Tale Of The Tape|access-date=February 10, 2022|work=Forbes|last=Konuwa|first=Alfred|date=April 7, 2018}} fixed stares on adversaries, protruding tongue displays, jolting of his head with a fury so that it faced the direction of his antagonists,{{cite news|url=https://www.mirror.co.uk/sport/other-sports/wrestling/wwe-producer-makes-shock-revelation-14058578|title=WWE producer makes shock revelation about The Undertaker's character|access-date=January 31, 2022|work=The Los Angeles Times|last=Smith|first=Alex|date=February 26, 2019}} his celebratory take-the-knee pose,{{cite news|url=https://bleedingcool.com/tv/wwe-smackdown-a-tribute-to-coronavi-we-mean-the-undertaker/|title=WWE SmackDown: A Tribute to Coronavi-… We Mean, The Undertaker|access-date=January 31, 2022|work=Bleeding Cool|last=Terror|first=Jude|date=June 26, 2020}} sonorous vocalizations,{{cite news|url=https://books.google.com/books?id=DcKMDwAAQBAJ&dq=deep+voice+undertaker+wwe&pg=PP48|title=Mayor Kane: My Life in wrestling and Politics|access-date=January 30, 2022|work=Center Street|last=Jacobs|first=Glenn|date=November 1, 2019|isbn=978-1-5460-8582-9 }} collectively labeling his fanbase as "Creatures of the Night",{{cite news|url=https://bleacherreport.com/articles/605887-wwes-looking-back-at-legends-best-feuds-of-the-biggest-stars-in-ppv-era-ep-3|title=WWE's Looking Back At Legends: Best Feuds Of the Biggest Stars in PPV Era, Ep. 3|access-date=March 12, 2022|work=Bleacher Report|last=Hubbs|first=Joe|date=February 11, 2011}} voice of God-like promos in which things were interrupted with dimmed lights and thunder while The Undertaker's communications were heard booming throughout the arena with no physical trace of him;{{cite news|url=https://www.youtube.com/watch?v=pO3YHHjuC10 |title=The Undertaker Delivers An Ominous Message To Stone Cold Before Rock Bottom! 12/13/98|access-date=May 4, 2014|work=WWE|date=October 5, 2022}} messages filled with death threats of a deeply posthumous insight into impending corpse decomposition, maggot feasting, unsouling and so on.{{cite news|url=https://www.today.com/popculture/tv/undertaker-wwe-hall-of-fame-2022-induction-ceremony-rcna21693|title=After 30 years as the Undertaker, a WWE legend rides off into the sunset|access-date=July 24, 2022|work=Today|last1=Lou|first1=Shane|date=March 29, 2022}} A main attraction of the Deadman gimmick, The Undertaker mesmerized his opponents and viewers alike through elaborately "bone-chilling" entrances.{{cite news|url=https://thewrestlingestate.com/index.php/2020/11/16/20-greatest-undertaker-entrances/|title=20 Greatest Undertaker Entrances|access-date=January 23, 2022|work=Wrestlingstate|last=Corrigan|first=John|date=November 16, 2020}} The character's godlike powers were routinely put on display in these moments, triggering lights back to the arena either gradually or suddenly dependent on his either slowly or abruptly raised arms. During the vast majority of his wrestling career as the Deadman, The Undertaker used an extended remix of Frédéric Chopin's Funeral March as his theme music.{{cite web |last=Allen |first=Ben |url=https://www.gq-magazine.co.uk/culture/article/the-undertaker-interview |title=The Undertaker is thinking about death now more than ever |date=June 11, 2020 |access-date=April 20, 2021 |work=GQ}} WWF Composer Jim Johnston embellished on the Chopin march, using the historic melody as a pre- and post-chorus to a main chorus of bell tolls, along with an original transition section to the song of a slow, lugubrious instrumental feel.{{cite news |last=Ross |first=Daniel |url=https://www.classicfm.com/discover-music/latest/classical-music-wrestling-entrance/ |title=Classical music and wrestling - 10 wrestlers who use classical entrance music |date=April 18, 2013 |access-date=April 20, 2021 |work=Classic FM}} Of his entrances, Calaway has stated, "When that gong went off, that was go time. The music fit the character. That's the key element of it: the end is at hand for whoever's going to be standing in that ring waiting for me to come down. That was the mindset behind the gong. And the music was just doom and gloom, you knew what was coming."{{cite news|url=https://www.yardbarker.com/wrestling/articles/the_undertaker_the_entrance_is_an_important_part_of_a_match_it_sets_the_tone/s1_16998_37914341|title=The Undertaker: The Entrance Is An Important Part Of A Match, It Sets The Tone|access-date=September 23, 2022|work=Yardbarker|last=Tessier|first=Colin|date=September 23, 2022}}

After a hiatus, Calaway returned in 2000 adopting a human form of the Undertaker gimmick. Under the character's alter ego, he is a semifictional smack-talking, redneck biker, thoroughly absent of his fully fictional Deadman zombie-like traits and wizardry. In performing this alternate identity, he rode to the ring on motorcycles, chewed tobacco, donned cargo garments and/or denim, printed shirts, and sporty fashion accessories (sunglasses, necklaces, bandanas).{{cite web |last=McCarrick |first=Michael |url=https://www.cbr.com/american-badass-wwes-realest-undertaker/ |title=American Badass: The Rise, Fall and Rebirth of WWE's REALEST Undertaker |date=April 4, 2020 |access-date=April 20, 2021 |work=Comic Book Resources}} His theme music was replaced with popular rock songs of the time, initially Kid Rock's "American Bad Ass" (from which The Undertaker's subtitle used to refer to this second identity derived), and eventually Limp Bizkit's "Rollin' (Air Raid Vehicle)".{{cite web |last=Beaston |first=Erik |url=https://bleacherreport.com/articles/2886330-the-evolution-of-the-undertakers-american-badass-character-in-wwe |title=The Evolution of The Undertaker's 'American Badass' Character in WWE |date=April 13, 2020 |access-date=April 20, 2021 |work=Bleacher Report}} His American Badass catch phrases, such as threats of “I'll make you famous” or references to the wrestling ring as his “yard”, became popular during this era. According to Bruce Prichard, Calaway requested this metamorphosis of character since he wanted to be "the biker–he wanted to be the guy that he is in everyday life".{{cite web |last=Thompson |first=Andrew |url=https://www.fightful.com/wrestling/bruce-prichard-explains-differences-thinking-between-creative-and-undertaker-about-american-badass |title=Bruce Prichard Explains The Differences In Thinking Between Creative And The Undertaker About The 'American Badass' Character |date=June 17, 2018 |access-date=October 30, 2020 |work=Fightful}}

While explained off-screen for the above reason years later, Calaway's sudden appearance as American Badass Undertaker after hiatus in which he left off as Deadman Undertaker was never explained within WWE storylines or the WWE's fictional universe. Rather, the expectation was for fans to just go with it. This transition lasted {{frac|3|1|2}} years until 2004 when The Undertaker resurrected his Deadman identity in hybrid form—residual features of his American Badass identity remaining. Among subtle details left over from his biker identity were his in-ring MMA style between his stances, strikes, and submissions; penchant to sporadically lower his tank top for a barechested appearance; celebrating victories with an arm-raised fist; etc. This hybrid Deadman (Deadman incarnation most closely based on Calaway himself) would last many years and for the remainder of The Undertaker's professional wrestling career, excluding his final wrestling match. For The Undertaker's final encounter, a Boneyard Match at WrestleMania 36 in 2020, he introduced a three-dimensional identity that brought all of his identities into one, dubbed "The Unholy Trinity:" a mix of his Deadman identity, American Badass identity, and his natural and genuine identity as Mark Calaway.

The Undertaker generated many nicknames from commentators throughout the course of his active wrestling career, some of those names more associated with his Deadman Undertaker identity, including "The Grim Reaper" (variants of this used were "The Reaper" and "The Reaper of Wayward Souls"),{{cite news |url=https://books.google.com/books?id=IPcwDQAAQBAJ&dq=The+Undertaker+Grim+Reaper&pg=PT193 |title=America Under Construction: Boundaries and Identities in Popculture (p. 172) |access-date=February 12, 2022|work=America Under Construction |last1=Long |first1=Kristi|last2=Nadelhaft|first2=Matthew|date=January 1, 2017|isbn=978-1-315-51187-0 }} "The Demon of Death Valley",{{cite news |url=https://books.google.com/books?id=zbwxAwAAQBAJ&dq=Demon+of+Death+Valley+The+Undertaker&pg=PA153 |title=WWE 50 (p. 153) |access-date=February 12, 2022|work=DK|last=Sullivan|first=Kevin|date=March 31, 2014|isbn=9781465427762 }} "The Man from the Dark Side",{{cite news |url=https://books.google.com/books?id=50EU6leHbLoC&dq=the+man+from+the+dark+side+the+undertaker&pg=PA67 |title=Wrestlecrap: The Very Worst of Professional Wrestling (p. 67)|access-date=February 12, 2022|work=ECW Press |last1=Baer |first1=Randy |last2=Reynolds |first2=R. D.|date=December 16, 2010|isbn=9781554905447 }} "The Prince of Darkness",{{cite news |url=https://books.google.com/books?id=PS0IBAAAQBAJ&dq=prince+of+darkness+the+undertaker&pg=PA105 |title=30 Years of WrestleMania (p. 105)|access-date=February 12, 2022|work=DK|last=Shields|first=Brian|date=January 1, 2014|isbn=9781465434203 }} "The Lord of Darkness".{{cite news|url=https://books.google.com/books?id=PS0IBAAAQBAJ&dq=Lord+of+Darkness+The+Undertaker&pg=PA187|title=30 Years of WrestleMania (p. 187)|access-date=February 12, 2022|work=DK|last=Shields|first=Brian|date=September 15, 2014|isbn=9781465434203 }} He also generated nicknames associated with his American Badass Undertaker identity, including "Big Evil" (used in reference to his American Badass heel side),{{cite news|url=https://books.google.com/books?id=zKL_BgAAQBAJ&dq=big+evil+the+undertaker&pg=PT240|title=Booker T: My Rise To Wrestling Royalty|access-date=February 12, 2022|work=Medallion Media Group|last1=Huffmann|first1=Booker T|last2=Wright|first2=Andrew|date=March 10, 2015|isbn=9781605427072 }} "Booger Red".{{cite web |url=https://411mania.com/wrestling/wwe-undertaker-failed-nickname/ |title=WWE News: The Undertaker Theme Music Helps Motivate Marine to Walk Again, Jim Ross Reveals His Failed Nickname for The Undertaker |date=July 7, 2018 |access-date=April 10, 2021 |work=411Mania}} Some of his nicknames were not identity specific but used for the character in general, such as "The Phenom".{{cite news |url=https://books.google.com/books?id=eQ86ax7XvzwC&dq=The+Phenom+American+Badass+biker&pg=PT137 |title=The WWE Yearbook 2003 Edition|access-date=February 12, 2022|work=WWE|last=McAvennie|first=Michael|date=June 30, 2008|isbn=9780743480628 }}

File:Brothers of Destruction.jpg

The Undertaker's gimmick has a dark and disturbed family backstory which involves him intentionally burning down his family funeral home as a teenager, resulting in the deaths of his parents and purportedly a brother of his as well. Undertaker initially denied his then ex-manager Paul Bearer's charges of him committing the arson murder of his family, (though later confessed in late 1998). Instead, Undertaker blamed his younger brother of whom he thought long dead from the incident, describing him as a "pyromaniac". This led to Bearer's shocking warnings to proof in the form of the brother, "Kane", as alive and well. In late 1997 at In Your House Badd Blood, Bearer unleashed a vengeful Kane: the fire-personified, juggernaut half-brother of Undertaker, who was fit with a mask to conceal the scarring from Undertaker's arson. In what became a fickle sibling relationship with Bearer (later revealed to be Kane's father) only adding to the pendulum and complexities, Undertaker and Kane went back and forth from one extreme to the other, feuding barbarically at points and yet teaming as the Brothers of Destruction at other points. In the duo's final feud in late 2009 through 2010, Kane emerged victorious in all of their matches.

The Undertaker's wrestling performance and move set were carried out with significant amounts of character-driven physical theater and kinesics. In keeping with his Deadman routine for example, Undertaker was forbiddingly slow and measured in much of his maneuvering and offense. Taking his opponents and audience by surprise, however, he combined his slow, measured physicality with wrestling moves and action uncharacteristic of a wrestler of his vast height and weight.{{cite news|url=https://www.essentiallysports.com/wwe-news-the-grind-never-ends-the-undertaker-looks-in-phenomenal-shape-at-56/|title="The Grind Never Ends"- the Undertaker Looks in Phenomenal Shape at 56|access-date=January 28, 2022|work=EssentiallySports|last=Fulgado|first=Nathan|date=May 26, 2021}} Not limited to just ground offense and power moves, Undertaker was conspicuously aerial, swift, agile, loose-limbed and animated in the other half of his wrestling style and move set: flying clotheslines,{{cite news |url=https://books.google.com/books?id=FV9CEAAAQBAJ&dq=the+undertaker+flying+clothesline&pg=PA182 |title=America Under Construction|access-date=January 23, 2022|work=Routledge|last1=Long|first1=Kristi|last2=Nadelhaft|first2=Matthew|date=January 1, 2017|isbn=9781315511887 }} guillotine leg drops,{{cite news|url=https://itrwrestling.com/news/the-undertaker-reveals-his-favourite-match-against-kane/|title=The Undertaker Reveals His Favourite Match Against Kane|access-date=January 23, 2022|work=Inside the Ropes|last=Goodwin|first=Jack|date=March 25, 2021}} running DDTs,{{cite news|url=https://www.essentiallysports.com/wwe-news-watch-when-undertaker-rose-to-the-heavens-after-a-casket-match-with-yokozuna-at-the-1994-royal-rumble/|title=WATCH: When Undertaker Rose to the Heavens After a Casket Match With Yokozuna at the 1994 Royal Rumble|access-date=January 28, 2022|work=EssentiallySports|last=Fulgado|first=Nathan|date=January 20, 2021}} ability to land on his feet poised and motionless if thrown from the ring, over-the-top-rope suicide dives{{cite news|url=https://books.google.com/books?id=rEfBDwAAQBAJ&dq=top+rope+undertaker+vs.+shawn+michaels+ground+zero&pg=PT30|title=The Main Event: The Moves and Muscle of Prowrestling|access-date=January 28, 2022|work=Lerner Publishing Group, Inc.|last=Jones|first=Patrick|date=January 1, 2013|isbn=9781512458039 }} (on one occasion, over the top rope and combined active flames during an Inferno match at In Your House Unforgiven), etc. During matches, Undertaker would also pay homage to Don Jardine by performing an arm twist ropewalk chop, dubbed "Old School".{{cite web |last=Matthews |first=Bobby |url=https://prowrestlingstories.com/pro-wrestling-stories/the-spoiler-don-jardine/ |title=The Spoiler Don Jardine: The Man Who Trained the Undertaker |date=May 20, 2017 |access-date=May 2, 2021 |work=Pro Wrestling Stories}}

Most famed for his Deadman Undertaker identity in particular, the role won Calaway the Wrestling Observer Newsletter awards for Best Gimmick a record-setting 5 years in a row (1990–1994). Calaway was highly protective of his Deadman public image: for the vast majority of his career while performing the gimmick, he was so private that he wasn't seen outside of character in the media. Calaway's approach of presenting only in character publicly was done in order to maintain the mystique of the Deadman and facilitate disbelief suspension.{{Cite web |url=http://411mania.com/wrestling/undertaker-character-today/|title=411MANIA|website=The Undertaker Discusses If Undertaker Character Would Be Successful If It Debuted Today, How Much He Did to Protect The Character}} However, during the last few years of his wrestling career, he allowed himself to be seen out of character, giving interviews as Mark Calaway and filming a documentary called The Last Ride.{{cite news |last1=Martínez |first1=Sebastián |title=Undertaker, sobre 'The Last Ride': 'Esta docuserie va a impresionar a la gente' |url=https://solowrestling.mundodeportivo.com/new/89444-undertaker-the-last-ride-docuserie-va-impresionar |access-date=March 14, 2022 |work=Solo Wrestling |date=May 8, 2020 |language=es}}

File:Varun Khanna and The Undertaker.jpg

The Undertaker has been named one of the greatest wrestlers of all time;{{cite web|url=https://www.skysports.com/wwe/news/14203/11516978/wwe-analysis-is-the-undertaker-the-greatest-of-all-time|title=WWE Analysis: Is The Undertaker the greatest of all time?|website=Sky Sports}} and the greatest character, and most iconic figure, in WWE history. He was voted the greatest WWE wrestler ever in a 2013 Digital Spy poll.{{cite web|title=The Undertaker voted greatest WWE Superstar of all time|url=http://www.digitalspy.co.uk/ustv/s216/wwe/news/a482978/the-undertaker-voted-greatest-wwe-superstar-of-all-time.html#~plW3SSuMcxWtpS|publisher=Digital Spy |access-date=August 21, 2015|date=May 20, 2013}} In naming him the second greatest wrestler ever, IGN described Undertaker as, "one of the most respected wrestlers, and characters, in the business; treated with actual reverence. Like a cherished, invaluable artifact".{{cite web |url=http://uk.ign.com/articles/2012/11/02/top-50-wrestlers-of-all-time?page=5|title=Top 50 Wrestlers of All Time|date=November 2, 2012|work=IGN}} Luis Paez-Pumar of Complex wrote that the Undertaker character is "easily the best gimmick in the history of professional wrestling".{{cite web |url=http://uk.complex.com/sports/2015/11/undertaker-10-best-matches-last-25-years/|title=The 10 Best Matches of 25 Years of the Undertaker |author=Luis Paez-Pumar |date=November 22, 2015|work=Complex}} Luke Winkie of Sports Illustrated listed Undertaker as the fifth greatest wrestler of all time.{{cite magazine |url=https://www.si.com/extra-mustard/2016/07/26/wwe-wcw-ecw-100-best-wrestlers-all-time|title=Ranking the top 101 wrestlers of all time |last=Winkie |first=Luke |magazine=Sports Illustrated|date=July 26, 2016|access-date=August 1, 2016}} His consecutive matches with Shawn Michaels at WrestleManias XXV and XXVI were met with critical acclaim, with both matches winning the Pro Wrestling Illustrated and Wrestling Observer Newsletter awards for Match of the Year in 2009 and 2010 respectively.{{cite web|url=http://www.pwi-online.com/pages/PWIawards.html|title=PWI Awards|work=Pro Wrestling Illustrated|publisher=Kappa Publishing Group|access-date=December 17, 2016|archive-date=January 21, 2016|archive-url=https://web.archive.org/web/20160121172943/http://www.pwi-online.com/pages/PWIawards.html|url-status=dead}}{{cite journal|last=Meltzer|first=Dave|author-link=Dave Meltzer|date=January 26, 2011|title=Biggest issue of the year: The 2011 Wrestling Observer Newsletter Awards Issue|periodical=Wrestling Observer Newsletter|location=Campbell, CA|pages=1–40|issn=1083-9593}} His Hell in a cell match with Triple H at WrestleMania XXVIII won the 2012 Slammy Award for the match of the year as well as being voted the match of the year on Pro Wrestling Illustrated.{{Cite web|url=https://www.wwe.com/shows/raw/2012-12-17/slammy-award-winner |title = 2012 WWE Slammy Awards and WWE.com Slammy Awards winners}}{{cite web |url=https://www.pwi-online.com/pages/PWIawards.html |title=PWI Awards |website=www.pwi-online.com |url-status=dead |archive-url=https://web.archive.org/web/20160121172943/http://www.pwi-online.com/pages/PWIawards.html |archive-date=January 21, 2016}}{{Cite web|url=https://solowrestling.mundodeportivo.com/new/96837-wwe-escoge-el-mejor-evento-estelar-de-wrestlemania|title = WWE escoge el Rock vs. Cena como el mejor main event de WrestleMania|date = March 15, 2021}}

Wrestler Big Show named The Undertaker as the greatest professional wrestler of all time,Archived at [https://ghostarchive.org/varchive/youtube/20211212/xfc79EMt2Io Ghostarchive]{{cbignore}} and the [https://web.archive.org/web/20160215031422/https://www.youtube.com/watch?v=xfc79EMt2Io&gl=US&hl=en Wayback Machine]{{cbignore}}: {{cite AV media|url=https://www.youtube.com/watch?v=xfc79EMt2Io&t=1m35s|title=Big Show Interview: On The Undertaker, Ultimate Warrior, leaving WWE, Hall of Fame|date=June 6, 2014|work=YouTube}}{{cbignore}} while Mark Henry and WWE chairman Vince McMahon have called him their favorite.{{cite web|url=http://www.wwe.com/classics/whos-your-favorite-wrestlers-favorite-wrestler/page-8|title=Who's your favorite wrestler's favorite wrestler?|work=WWE}}{{cite web|url=http://www.muscleandfitness.com/athletes-celebrities/interviews/wwe-chief-vince-mcmahon-still-making-gains?page=4&cc=GB|title=WWE Chief Vince McMahon Is Still Making Gains|work=Muscle & Fitness|date=July 6, 2015}} WWE Hall of Famer and former company executive, Jim Ross, said: "Without question, The Undertaker is the greatest big man in the history of wrestling... There is no greater WWE star ever than The Undertaker".{{cite web|url=http://www.wwe.com/classics/classic-lists/the-20-most-dangerous-superstars|title=The 20 most dangerous Superstars ever|last=Linder|first=Zach|publisher=WWE|access-date=April 2, 2016}}

Guinness World Records Gamer's Edition recognized Undertaker as having the most consecutive victories at WrestleMania in 2016.{{cite book|url=https://books.google.com/books?id=7s96CgAAQBAJ&q=undertaker+guinness+world+records&pg=PA174|title=Guinness World Records Gamer's Edition 2016|isbn=9781910561102|last1=Records|first1=Guinness World|date=September 10, 2015|publisher=Guinness World Records }} In November 2015, Telegraph journalist Tom Fordy called Undertaker "the world's greatest sportsman".{{Cite news|url=https://www.telegraph.co.uk/men/the-filter/why-the-undertaker-is-the-worlds-greatest-sportsman/ |archive-url=https://ghostarchive.org/archive/20220110/https://www.telegraph.co.uk/men/the-filter/why-the-undertaker-is-the-worlds-greatest-sportsman/ |archive-date=January 10, 2022 |url-access=subscription |url-status=live|title=Why the Undertaker is the world's greatest sportsman|first=Tom|last=Fordy|website=The Telegraph|date=November 22, 2015|access-date=December 19, 2019}}{{cbignore}} The Undertaker is also one of two wrestlers (the other being The Rock) that has main evented WrestleMania in four different decades: 1990s: 13 (1997); 2000s: XXIV (2008); 2010s: XXVI (2010), 33 (2017); 2020s: 36 (2020).

Undertaker's Deadman character in particular has been praised as one of the best in professional wrestling. He received the Wrestling Observer Newsletter's Best Gimmick award from 1990 to 1994. Tim Friorvant of ESPN named Undertaker "a character that has been a cornerstone of the WWE for more than three decades".{{cite web|url=http://www.espn.com/wwe/story/_/id/23293794|title=New Undertaker graphic novel set to dig deeper into career of one of WWE's biggest icons|date=April 23, 2018|website=ESPN.com}} Shawn Valentino of Pro Wrestling Torch said "The Undertaker may have been the greatest character in the history of professional wrestling".{{cite web|url=https://www.pwtorch.com/site/2017/05/05/magic-memories-mania-top-10-undertaker-matches-mankind-punk-michaels-triple-h-finished-first/|title=MAGIC, MEMORIES AND MANIA: Top 10 Undertaker Matches from Mankind to Punk to Michaels to Triple H, which finished first? -|last=Dr.Gonzo|date=May 5, 2017}}

A 12-minute match between Undertaker and Stone Cold Steve Austin drew a 9.5 rating on June 28, 1999. It stands as the highest-rated segment in Raw history.{{Cite web|url=https://uproxx.com/prowrestling/monday-night-raw-highest-rated-segment-all-time/|title=Revisit The Highest-Rated Segment In The History Of Monday Night Raw|date=September 28, 2016|website=UPROXX|access-date=November 24, 2019}}

File:Undertaker, broken.jpg in April 2014.]]

In contrast to the high praise The Undertaker received during the vast majority of his professional wrestling career, he was heavily criticized for continuing to perform throughout the latter part of his wrestling career, particularly after his first defeat at WrestleMania in 2014. Calaway would later reveal that after suffering a severe concussion in his WrestleMania match against Lesnar, he lost his confidence.{{Cite web|url=https://solowrestling.mundodeportivo.com/new/89497-the-undertaker-grave-conmocion-en-wrestlemania-30|title=The Undertaker: 'Una conmoción en un sólo combate destruyó mi confianza'|date=May 11, 2020|website=solowrestling.mundodeportivo.com}} At WrestleMania 33, after his second defeat against Roman Reigns, Luis Paez-Pumar of Rolling Stone said that Undertaker "should have retired when The Streak was broken" but "lived on to pass the rub on to Reigns in the sloppiest, saddest manner possible".{{cite web|last1=Paez-Pumar|first1=Luiz|title=7 'WrestleMania 33' Takeaways: What Comes Next for WWE Superstars|url=https://www.rollingstone.com/sports/7-wrestlemania-33-takeaways-what-comes-next-for-wwe-w474594|publisher=Rolling Stone|access-date=April 3, 2017|date=April 3, 2017}} Undertaker himself said he was disappointed by his performance against Reigns.{{Cite web|url=https://solowrestling.mundodeportivo.com/new/89447-undertaker-decepcion-roman-reigns-wrestlemania|title=The Undertaker revela su decepción por el combate contra Roman Reigns en WrestleMnaia 33|date=May 8, 2020|website=solowrestling.mundodeportivo.com}} After his match against John Cena at WrestleMania 34, IGN posted an article titled "Undertaker's return was awesome, but now he needs to retire".{{cite web|url=https://www.ign.com/articles/2018/04/09/undertakers-return-was-awesomebut-now-he-needs-to-retire|title=The Undertaker's WrestleMania Return Was Awesome...But Now He Needs to Retire|first=Matt|last=Fowler|date=April 9, 2018}} After his match at Crown Jewel in November 2018, Pro Wrestling Torch{{'}}s Wade Keller wrote that Undertaker looked "brittle"{{cite web|url=https://www.pwtorch.com/site/2018/11/02/wwe-crown-jewel-results-11-2-kellers-report-on-styles-vs-joe-strowman-vs-lesnar-world-cup-tournament-michaels-triple-h-vs-kane-undertaker/|title=WWE CROWN JEWEL RESULTS 11/2: Keller's report on Styles vs. Joe, Strowman vs. Lesnar, World Cup tournament, Michaels & Triple H vs. Kane & Undertaker|publisher=Pro Wrestling Torch|first=Wade|last=Keller|author-link=Wade Keller|date=November 2, 2018|access-date=November 2, 2018}} and Jason Powell of Pro Wrestling Dot Net said "they [Undertaker, Kane, Michaels and Triple H] need to accept their limitations, stop pretending they belong in main events, and stop acting like being in these main events isn't stealing the spotlight".{{cite web|last=Powell|first=Jason|title=Powell's WWE Crown Jewel live review: Brock Lesnar vs. Braun Strowman for the vacant WWE Universal Championship, AJ Styles vs. Samoa Joe for the WWE Championship, Undertaker and Kane vs. DX, World Cup tournament|url=https://prowrestling.net/site/2018/11/02/powells-wwe-crown-jewel-live-review-brock-lesnar-vs-braun-strowman-for-the-vacant-wwe-universal-championship-aj-styles-vs-samoa-joe-for-the-wwe-championship-undertaker-and-kane-vs-dx-wor/|work=Pro Wrestling Dot Net|access-date=November 2, 2018|date=November 2, 2018}} His subsequent match with Goldberg at Super ShowDown in June 2019 was also widely pilloried, with Bryan Rose of the Wrestling Observer Newsletter calling it "sad more than anything".{{cite web|url=https://www.f4wonline.com/wwe-results/wwe-super-showdown-live-results-undertaker-vs-goldberg-285506|title=WWE Super ShowDown live results: The Undertaker vs. Goldberg|first=Bryan|last=Rose|date=June 7, 2019|access-date=June 9, 2019|work=Figure Four Online}} In reviewing the show, Dave Meltzer of the same publication wrote that Goldberg "has juice left, while Undertaker doesn't".{{cite web |last1=Meltzer |first1=Dave |author-link1=Dave Meltzer |title=June 17, 2019 Observer Newsletter: Scary incidents in the ring, NJPW Dominion review |url=https://members.f4wonline.com/wrestling-observer-newsletter/june-17-2019-observer-newsletter-scary-incidents-ring-njpw-dominion |website=f4wonline.com |access-date=June 17, 2019}}{{subscription required}} Undertaker himself called the match "a disaster" in 2020.{{Cite web|url=https://solowrestling.mundodeportivo.com/new/89711-the-undertaker-last-ride-episodio-3-resumen|title=The Undertaker: 'El combate de WWE Crown Jewel 2018 fue un desastre'|date=May 22, 2020|website=solowrestling.mundodeportivo.com}}

Despite the media criticism, two of Undertaker's later matches—teaming with Roman Reigns against Drew McIntyre and Shane McMahon at Extreme Rules 2019, as well as his cinematic Boneyard match against AJ Styles at WrestleMania 36—were both widely praised, with critics citing both matches as his best performances in recent years. The former would be ranked #25 on WWE.com's 25 best matches of 2019, and the latter was ranked #1 on WWE.com's 25 best matches of 2020. The Boneyard match would also win WWE's Half-Year Award for best Cinematic Match, as well as winning the Slammy Award for 2020's Match of the Year.{{Cite web|title=The Top 25 Matches of 2019|url=https://www.wwe.com/article/top-25-matches-of-2019|website=WWE}}{{Cite web|url=https://www.wwe.com/article/25-best-matches-2020|title=What was the best match of 2020?|website=WWE|accessdate=March 17, 2023}}

{{cite news |last=Bixenspan |first=David |title=WrestleMania Still Happened Last Weekend. Without Fans. It Was Weird. |url=https://slate.com/culture/2020/04/wrestlemania-36-no-fans-audience-coronavirus-undertaker-john-cena.html |access-date=November 26, 2020 |work=Slate Magazine |date=April 7, 2020}}{{cite news |last=Mueller |first=The Doctor Chris |title=WWE WrestleMania 36 Results: Winners, Grades, Reaction and Highlights from Day 1 |url=https://bleacherreport.com/articles/2885079-wwe-wrestlemania-36-results-winners-grades-reaction-and-highlights-from-day-1 |access-date=November 26, 2020 |work=Bleacher Report |date=April 5, 2020}}

File:McCool & Undertaker 2019.jpg

Calaway married Jodi Lynn in 1989. They had a son in 1993 and divorced in 1999.{{cite web|url=https://www.ibtimes.co.in/undertakers-wife-michelle-mccool-reveals-first-ever-photo-their-daughter-722349|title=Undertaker's wife Michelle McCool reveals first-ever photo of their daughter|date=April 7, 2017|last=Maitra|first=Sayantan|access-date=February 19, 2018|work=International Business Times}} Calaway married Sara Frank in 2000, and she made televised appearances with WWE in 2001 as part of a feud between Calaway and Diamond Dallas Page, in which she was acknowledged as Calaway's wife. They had two daughters before divorcing in 2007. In 2010, Calaway married former professional wrestler Michelle McCool.{{cite web|url=https://www.wrestleview.com/wwe-news/15177-report-wwe-stars-wed-this-past-week/|url-status=live |archive-url=https://web.archive.org/web/20230204214523/https://www.wrestleview.com/wwe-news/15177-report-wwe-stars-wed-this-past-week/ |archive-date=February 4, 2023| last=Martin| first=Adam| title=Report: WWE stars wed this past week|work=WrestleView|date=June 29, 2010|access-date=July 5, 2010}} They have a daughter born in 2012 and an adopted son.{{cite web|url=https://sportprat.com/es/el-hijo-de-3-anos-de-the-undertaker-dice-su-primera-palabrota-y-todo-gracias-a-la-leyenda-millonaria-de-la-nfl/|archive-url=https://web.archive.org/web/20221024170844/https://sportprat.com/es/el-hijo-de-3-anos-de-the-undertaker-dice-su-primera-palabrota-y-todo-gracias-a-la-leyenda-millonaria-de-la-nfl/|url-status=dead|archive-date=October 24, 2022|title=El hijo de 3 años de The Undertaker dice su primera palabrota y todo gracias a la leyenda millonaria de la NFL|publisher=Sportprat|language=ES|date=August 8, 2022|access-date=October 24, 2022}}

In the 1990s, Calaway started a backstage "posse" called the Bone Street Krew which consisted of some of his best friends and fellow wrestlers Yokozuna, Savio Vega, Charles Wright, The Godwinns, and Rikishi. Each member had the initials "BSK" tattooed onto themselves, with Calaway's prominently marked across his stomach.{{cite web|url=http://www.wwe.com/inside/undertaker-bone-street-krew-bsk-history-28197200|title=The uncensored history of The Undertaker's locker room group: The Bone Street Krew|work=WWE|access-date=February 6, 2016|archive-date=January 30, 2016|archive-url=https://web.archive.org/web/20160130004225/http://www.wwe.com/inside/undertaker-bone-street-krew-bsk-history-28197200|url-status=dead}}

Calaway is a fan of boxing and mixed martial arts, which he incorporated into his onscreen character. He has practiced Brazilian jiu-jitsu and earned a black belt in 2011.{{Cite web|date=February 6, 2021|title=Did you know that WWE's The Undertaker has a Black Belt in Brazilian Jiu Jitsu?|url=https://bjjtribes.com/did-you-know-that-wwes-the-undertaker-has-a-black-belt-in-brazilian-jiu-jitsu/|access-date=April 19, 2021|website=BjjTribes}} He invests in real estate with his business partner, Scott Everhart. The two finished construction on a $2.7 million building in Loveland, Colorado, called "The Calahart" (a portmanteau of their last names), in 2007.{{cite web|url=http://www.wrestleview.com/news2006/1182096452.shtml|last=Martin|first=Adam|title=The Undertaker gets involved in real estate venture; his return to WWE|access-date=August 21, 2007|date=June 17, 2007|publisher=WrestleView}} A dog lover, Calaway and his ex-wife Sara established The Zeus Compton Calaway Save the Animals Fund at the Texas A&M College of Veterinary Medicine & Biomedical Sciences to help pay for lifesaving treatments for large dogs.{{Cite web|url=http://www.cvm.tamu.edu/zeusfund/index.shtml|title=The Zeus Compton Calaway Save the Animals Fund|access-date=December 19, 2019|archive-url=https://web.archive.org/web/20050204000948/http://www.cvm.tamu.edu/zeusfund/index.shtml|archive-date=February 4, 2005}}

In June 2020, Calaway expressed support for the Blue Lives Matter movement.{{cite news|url=https://popculture.com/sports/news/wwe-undertaker-taking-heat-blue-lives-matter-support/|title=WWE: Undertaker Taking Heat for Blue Lives Matter Support|access-date=February 21, 2022|work=Pop Culture|last=Newby|first=John|date=June 7, 2020}} Later that year, Dave Meltzer reported that Calaway had made several donations totaling $7,000 to Donald Trump's re-election campaign.{{cite web|last=Meltzer|first=Dave|authorlink=Dave Meltzer|date=October 30, 2020|title=November 2, 2020 Observer Newsletter: WWE Q3 financials, more|url=https://www.f4wonline.com/newsletters/wrestling-observer-newsletter/november-2-2020-observer-newsletter-wwe-q3-financials-more-323936|access-date=February 4, 2021|work=Wrestling Observer Newsletter|url-access=subscription}} In February 2021, Calaway stated that he would endorse fellow wrestler Dwayne Johnson if he were to ever run for president, expressing that he felt Johnson could be the great "uniter" and ease the American political divide.{{cite news|url=https://nypost.com/2021/02/23/dwayne-the-rock-johnson-endorsed-for-president/|title=Dwayne 'The Rock' Johnson endorsed for president by WWE's Undertaker|access-date=February 21, 2022|work=New York Post|last=Sparks|first=Hannah|date=February 23, 2021}} Calaway and Glenn Jacobs endorsed Trump in the 2024 United States presidential election, appearing in a TikTok with him which featured them calling out fellow wrestler Dave Bautista, who had been outspoken against Trump.{{Cite web |date=October 18, 2024 |title=Take Your Pick |url=https://www.tiktok.com/@realdonaldtrump/video/7427237451954965791 }}

Calaway made his acting debut as Hutch in the 1991 film Suburban Commando.{{cite web|url=https://www.rottentomatoes.com/m/suburban_commando/|title=Suburban Commando|website=Rotten Tomatoes|access-date=April 26, 2018}} He had guest roles on Poltergeist: The Legacy and Celebrity Deathmatch. In 2002, he appeared on the Canadian sports show Off the Record with Michael Landsberg.

On January 15, 2022, Donald Trump used The Undertaker's theme music as part of his "Save America" rally held in Florence, Arizona. The song that was played incorporates funeral bell tolls and was created by WWE composer Jim Johnston as an embellished remix of "Funeral March". During the rally, the song was accompanied by a music video playing on large screens, advancing through multitudes of scenes intended to alarm the public of looming danger resulting from the presidency of Trump's successor Joe Biden. The song continued to play out for 30 seconds following the attack ad against Biden, ending just short of Trump making his entrance. Other than his music being played, Calaway was not reported to have any association with the affair, though he had previously donated to Trump's campaign in 2020 and would later endorse him in 2024.{{cite news|url=https://www.businessinsider.com/trump-arizona-rally-walkout-song-wwe-wrestler-the-undertaker-2022-1|title=Trump was introduced at his Arizona rally with the walkout song for WWE wrestler The Undertaker|access-date=January 16, 2022|work=Business Insider|last=Vlamis|first=Kelsey|date=January 16, 2022}}{{cite news|url=https://trixabia.com/trump-was-featured-at-his-arizona-rally-with-wwe-wrestler-the-undertakers-exit-song/|title=Trump was featured at his Arizona rally with WWE wrestler The Undertaker's exit song|access-date=January 16, 2022|work=Trixabia|date=January 16, 2022|archive-date=January 16, 2022|archive-url=https://web.archive.org/web/20220116120735/https://trixabia.com/trump-was-featured-at-his-arizona-rally-with-wwe-wrestler-the-undertakers-exit-song/|url-status=dead}}

In 2025, he would appear in the documentary film Wrestlemania IX: The Spectacle. The documentary was released on Peacock on April 11, 2025.{{cite news|url=https://www.nbc.com/nbc-insider/wrestlemania-ix-becoming-a-spectacle-trailer|title=WWE's New Peacock Doc Reveals the Shocking Events Behind WrestleMania in 1993|first=Tyler|last=McCarthy|publisher=NBC News|date=April 2, 2025|accessdate=April 11, 2025}}{{cite web|url=https://www.wwe.com/shows/wrestlemania/article/wrestlemania-ix-becoming-a-spectacle-premieres-friday-april-11-on-peacock|title=WrestleMania IX: Becoming a Spectacle premieres Friday, April 11, on Peacock|publisher=WWE.com|date=April 2, 2025|accessdate=April 11, 2025}}

Calaway's WWE character has been included in numerous WWE video games, beginning with WWF Super WrestleMania (1992).{{cite web|url=https://segaretro.org/WWF_Super_WrestleMania|title=WWF Super WrestleMania|work=SegaRetro|access-date=May 30, 2019}} A special Undertaker-themed version of WWE 2K14 was released in 2013.{{cite web|url=https://www.polygon.com/2013/8/1/4579124/wwe-2k14-phenom-edition-undertaker-autograph-coffin#0|title=WWE 2K14 Phenom Edition puts Undertaker in tin coffin|last=Sarkar|first=Samit|date=August 1, 2013|access-date=May 30, 2019|work=Polygon}} The Undertaker is also the most featured wrestler in WWF/E's video game collection, having been presented on every game in the franchise.

File:The Undertaker Wins!.jpg World Heavyweight Champion.]]

• The Baltimore Sun
• Feud of the Year (2007) {{small|vs. Batista}}{{cite web|last=Eck|first=Kevin|title=2007 Awards|url=https://www.baltimoresun.com/bs-mtblog-2007-12-2007_awards-story.html|work=The Baltimore Sun|date=December 30, 2007|access-date=September 25, 2020|archive-date=October 26, 2020|archive-url=https://web.archive.org/web/20201026135318/https://www.baltimoresun.com/bs-mtblog-2007-12-2007_awards-story.html|url-status=dead}}
• Best Match of the Decade (2000s) {{small|vs. Shawn Michaels at WrestleMania 25}}{{cite web|last=Eck|first=Kevin|title=Best of the Decade awards|url=https://www.baltimoresun.com/bs-mtblog-2010-01-best_of_the_decade_awards-story.html|work=The Baltimore Sun|date=January 11, 2010|access-date=December 20, 2020|archive-date=February 4, 2021|archive-url=https://web.archive.org/web/20210204084558/https://www.baltimoresun.com/bs-mtblog-2010-01-best_of_the_decade_awards-story.html|url-status=dead}}
• Match of the Year (2009) {{small|vs. Shawn Michaels at WrestleMania 25}}{{cite web|last=Eck|first=Kevin|title=2009 Awards|url=https://www.baltimoresun.com/bs-mtblog-2010-01-2009_awards-story.html|work=The Baltimore Sun|date=January 27, 2010|access-date=September 25, 2020|archive-date=October 26, 2020|archive-url=https://web.archive.org/web/20201026135227/https://www.baltimoresun.com/bs-mtblog-2010-01-2009_awards-story.html|url-status=dead}}
• Match of the Year (2010) {{small|vs. Shawn Michaels in a career vs. streak match at WrestleMania XXVI}}{{cite web|last=Eck|first=Kevin|title=2010 Awards|url=https://www.baltimoresun.com/bs-mtblog-2011-02-2010_awards-story.html|work=The Baltimore Sun|date=February 14, 2011|access-date=September 25, 2020|archive-date=June 5, 2022|archive-url=https://web.archive.org/web/20220605095538/https://www.baltimoresun.com/bs-mtblog-2011-02-2010_awards-story.html|url-status=dead}}
• CBS Sports
• Worst Angle of the Year (2018) {{small|with Kane vs. Triple H and Shawn Michaels}}{{cite web|url=https://www.cbssports.com/wwe/news/the-man-comes-around-becky-lynch-breaks-out-for-wwe-as-the-2018-wrestler-of-the-year/|title=The Man comes around: Becky Lynch breaks out for WWE as the 2018 Wrestler of the Year|last=Silverstein|first=Adam|date=December 26, 2018|work=CBS Sports}}
• Pro Wrestling Illustrated
• Comeback of the Year (2015)
• Feud of the Year (1991) {{small|vs. The Ultimate Warrior}}
• Feud of the Year (2015) {{small|vs. Brock Lesnar}}
• Match of the Year (1998) {{small|vs. Mankind in a Hell in a Cell match at King of the Ring}}
• Match of the Year (2009) {{small|vs. Shawn Michaels at WrestleMania 25}}
• Match of the Year (2010) {{small|vs. Shawn Michaels in a career vs. streak match at WrestleMania XXVI}}
• Match of the Year (2012) {{small|vs. Triple H in a Hell in a Cell match at WrestleMania XXVIII}}
• Ranked No. 2 of the top 500 singles wrestlers in the PWI 500 in 2002{{cite web|url=http://profightdb.com/pwi-500/2002.html|title=Pro Wrestling Illustrated (PWI) 500 for 2002|publisher=The Internet Wrestling Database|access-date=August 25, 2015}}
• Ranked No. 21 of the top 500 singles wrestlers of the "PWI Years" in 2003{{cite web|url=http://www.willywrestlefest.fr/Ressources/PWI/PWI500_PWI_Years_2003.htm|title=PWI 500 of the PWI Years|access-date=January 16, 2019}}
• Sports Illustrated
• Ranked No. 6 of the 20 Greatest WWE Wrestlers Of All Time {{cite magazine |last1=Pullar III |first1=Sid |date=October 13, 2024 |title=20 Greatest WWE Wrestlers Of All Time |url=https://www.si.com/fannation/wrestling/features/10-greatest-wwe-wrestlers-of-all-time |magazine=Sports Illustrated |access-date=November 26, 2024}}
• United States Wrestling Association
• USWA Unified World Heavyweight Championship (1 time){{cite web | url=http://www.wrestling-titles.com/us/tn/uswa/uswa-uh.html | title=Unified World Heavyweight Title [United States Wrestling Association] | access-date=March 28, 2017 | work=Wrestling-Titles}}
• World Class Wrestling Association
• WCWA Texas Heavyweight Championship (1 time){{cite book| last1=Will | first1=Gary | first2=Royal | last2= Duncan | title=Wrestling Title Histories: professional wrestling champions around the world from the 19th century to the present | publisher=Archeus Communications | year=2000 | location=Pennsylvania | chapter=Texas: NWA Texas Heavyweight Title [Von Erich] | isbn=0-9698161-5-4 | pages=268–269}}{{cite web | url=http://www.wrestling-titles.com/us/tx/tx-h.html | title= NWA Texas Heavyweight Title | access-date=March 30, 2017 | work=Wrestling-Titles}}
• World Wrestling Federation / Entertainment / WWE
• WWF/WWE Championship (4 times)[http://www.wrestling-titles.com/wwe/wwf-h.html WWWF/WWF/WWE World Heavyweight Title history] At wrestling-titles.com
• World Heavyweight Championship (3 times)[http://www.wrestling-titles.com/wwe/wwe-world-h.html World Heavyweight Title (WWE Smackdown!) history] At wrestling-titles.com
• WWF Hardcore Championship (1 time)[http://www.wrestling-titles.com/wwe/wwf-hc.html WWF/WWE Hardcore Title history] At wrestling-titles.com
• WWF World Tag Team Championship (6 times) – with Stone Cold Steve Austin (1), Big Show (2), The Rock (1), and Kane (2)[http://www.wrestling-titles.com/wwe/wwf-t.html WWWF/WWF/WWE World Tag Team Title history] At wrestling-titles.com
• WCW Tag Team Championship (1 time) – with Kane{{Efn|Won during The Invasion}}[http://www.wrestling-titles.com/wcw/wcw-t.html WCW World Tag Team Title history] At wrestling-titles.com
• Royal Rumble (2007)
• WWE Hall of Fame (Class of 2022)
• Tuwaiq Mountain Trophy (2020)
• Undisputed WWF Championship #1 contender's Tournament (April 2002)
• Slammy Award (15 times)
• Best Entrance Music (1997){{cite web|url=http://www.prowrestlinghistory.com/supercards/usa/wwf/slammy.html#97|title=Slammy Awards — 1997|work=Pro Wrestling History|access-date=January 24, 2019}}
• Best Tattoo (1997)
• Match of the Year (2009, 2010, 2012, 2015, 2020) {{small|vs. Shawn Michaels at WrestleMania 25}}, {{small|vs. Shawn Michaels at WrestleMania XXVI}}, {{small|vs. Triple H in a Hell in a Cell match at WrestleMania XXVIII}}, {{small|vs. Brock Lesnar at Hell in a Cell}}, {{small|and vs. AJ Styles in a Boneyard match at WrestleMania 36}}.{{cite news|url=http://www.wwe.com/shows/raw/slammyawards09/|title=2009 Slammy Awards|archive-url=https://web.archive.org/web/20091217075351/http://www.wwe.com/shows/raw/slammyawards09/|archive-date=December 17, 2009|url-status=dead|access-date=April 28, 2018|publisher=WWE}}{{cite web|url=http://www.wwe.com/shows/raw/slammyawards10/|title=2010 Slammy Awards|archive-url=https://web.archive.org/web/20101218194038/http://www.wwe.com/shows/raw/slammyawards10/|archive-date=December 18, 2010|url-status=dead|access-date=April 28, 2018|publisher=WWE}}{{cite web|url=http://www.wwe.com/shows/raw/2012-12-17/slammy-award-winners|title=2012 WWE Slammy Awards and WWE.com Slammy Awards winners|access-date=April 28, 2018|publisher=WWE}}{{cite news|url=http://www.wwe.com/shows/raw/2015-12-21/2015-slammy-award-winners|title=2015 Slammy Award winners|date=December 16, 2015|access-date=April 27, 2018|newspaper=WWE}}
• Moment of the Year (2010) {{small|vs. Shawn Michaels at WrestleMania XXVI}}
• Most Intimidating (1994){{cite web|url=http://www.thewrestlinginsomniac.com/2015/11/wwf-1994-slammy-awards.html|title=WWF 1994 Slammy Awards|first=Michael J.|last=Labbe}}
• OMG Moment of the Year (2011) {{small|Kicking out of Triple H's Tombstone Piledriver at WrestleMania XXVII}}{{cite web|url=http://www.wwe.com/shows/raw/2011-12-12/exclusive-slammy-awards-2011|title=WWE.com Exclusive Slammy Awards 2011|access-date=April 28, 2018|publisher=WWE}}
• Rivalry of the Year (2015) {{small|vs. Brock Lesnar}}
• Star of the Highest Magnitude (1997)
• WWF's Greatest Hit (1996) {{small|Sucking Diesel into the abyss at In Your House 6: Rage in the Cage}}{{cite web|url=http://www.prowrestlinghistory.com/supercards/usa/wwf/slammy.html#96|title=Slammy Awards — 1996|work=Pro Wrestling History}}
• Moment of the Year (2020) {{small|The Undertaker's final farewell at Survivor Series}}
• WWE Network Documentary of the Year (2020) {{small|Undertaker: The Last Ride}}
• NXT Year-End Award
• Moment of the Year (2023 - appearing on the October 10 episode of NXT)
• WWE Bronze Statue (2022){{cite web|url=https://www.wwe.com/article/the-undertakers-statue-revealed-at-wrestlemania-axxess|title=The Undertaker's statue revealed at WrestleMania Axxess|publisher=WWE|date=March 31, 2022|access-date=April 15, 2022}}
• Wrestling Observer Newsletter
• Best Gimmick (1990–1994)
• Best Heel (1991)
• Feud of the Year (2007) {{small|vs. Batista}}
• Match of the Year (2009) {{small|vs. Shawn Michaels at WrestleMania 25}}
• Match of the Year (2010) {{small|vs. Shawn Michaels in a career vs. streak match at WrestleMania XXVI}}
• Worst Worked Match of the Year (2001) {{small|with Kane vs. KroniK at Unforgiven}}
• Worst Match of the Year (2018) {{small|with Kane vs. Triple H and Shawn Michaels at Crown Jewel}}{{cite web|url=https://www.postwrestling.com/2019/03/17/bonus-show-wrestling-observer-newsletter-awards/|title=BONUS SHOW: Wrestling Observer Newsletter Awards|date=March 17, 2019|access-date=March 23, 2019|work=Post Wrestling}}
• Most Overrated (2001)
• Readers' Least Favorite Wrestler (2001)
• Worst Feud of the Year (1993) {{small|vs. Giant González}}
• Most Disgusting Promotional Tactic (2005) {{small|Involvement in a terrorist angle that aired on day of London bombings}}
• Wrestling Observer Newsletter Hall of Fame (Class of 2004){{cite web|url=http://www.pwi-online.com/pages/hallofame.html|title=Wrestling Observer Newsletter Hall of Fame|access-date=January 24, 2019|archive-date=November 12, 2015|archive-url=https://web.archive.org/web/20151112104543/http://www.pwi-online.com/pages/hallofame.html|url-status=dead}}

• Eyegore Award (2000)Archived at [https://ghostarchive.org/varchive/youtube/20211212/3IqMaa4lKCw Ghostarchive]{{cbignore}} and the [https://web.archive.org/web/20160316003448/https://www.youtube.com/watch?v=3IqMaa4lKCw Wayback Machine]{{cbignore}}: {{cite AV media|url=https://www.youtube.com/watch?v=3IqMaa4lKCw|title=THE UNDERTAKER accepts 2000 Eyegore Horror Award with explosive arrival|date=March 8, 2013|via=YouTube}}{{cbignore}}{{Cite web|url=http://www.imdb.com/event/ev0001545/2000/1/|title=Eyegore Awards (2000)|website=IMDb}}

{{Main|The Streak (professional wrestling)}}

{{Notelist}}

{{reflist}}

{{Commons category|Mark Calaway|The Undertaker}}

• {{wwe superstar|name = The Undertaker}}
• [https://archive.org/search?query=undertaker The Undertaker] on the Internet Archive
• {{Facebook}}
• {{IMDb name|name=Mark Calaway}}
• {{Professional wrestling profiles}}

{{The Undertaker|state=expanded}}

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