Shawn Michaels#Personal life

Michael Shawn Hickenbottom was born in Chandler, Arizona, on July 22, 1965.{{harv|Michaels|Feigenbaum|2005|pp=12–13}}{{cite web|url=http://slam.canoe.com/Slam/Wrestling/Bios/michaels-shawn.html|archive-url=https://web.archive.org/web/20150522073938/http://slam.canoe.com/Slam/Wrestling/Bios/michaels-shawn.html|url-status=dead|archive-date=May 22, 2015|title=Slam! Sports biography|access-date= July 10, 2007|publisher=Canadian Online Explorer|work=Slam! Sports|date=March 12, 2005|last=Milner|first=John|author2=Jason Clevett }} He has an older sister named Shari and two older brothers named Randy and Scott. He was raised in a military family and briefly spent some of his early years in the English town of Reading, Berkshire, but grew up primarily in San Antonio, Texas. As a child, he disliked the name "Michael" and convinced his family and friends to address him by his middle name.{{Harv|Michaels|Feigenbaum|2005|pp=18–19}} Ever since, he has been referred to as Shawn. Additionally, Hickenbottom moved around frequently since his father was in the military. He knew he wanted to become a professional wrestler at the age of 12 and performed a wrestling routine at his high school's talent show, complete with fake blood.{{cite web|url=https://www.af.mil/News/Article-Display/Article/136347/professional-wrestler-visits-former-base-school-home/|title=Professional wrestler visits former base school, home|work=U.S. Air Force |date=August 6, 2004 }} He was a keen athlete while growing up, and his sporting career began at the age of six when he played football.{{Harv|Michaels|Feigenbaum|2005|p=15}} He was a stand-out linebacker at Randolph High School on Randolph Air Force Base and eventually became captain of the football team.{{cite web|url=http://www.wwe.com/superstars/halloffame/inductees/hbk/|title=Shawn Michaels' WWE Hall of Fame Profile|access-date=March 31, 2011|publisher=World Wrestling Entertainment}}{{Harv|Michaels|Feigenbaum|2005|p=30}} He attended Southwest Texas State University in San Marcos, Texas, but dropped out to pursue a career in professional wrestling.{{Harv|Michaels|Feigenbaum|2005|pp=43–49}} His cousin Matt Bentley is also a wrestler.{{cite web|first=John M.|last=Milner|author2=Jaya Roopansingh|url=http://slam.canoe.ca/Slam/Wrestling/Bios/bentley-matt.html|archive-url=https://archive.today/20120714011715/http://slam.canoe.ca/Slam/Wrestling/Bios/bentley-matt.html|url-status=usurped|archive-date=July 14, 2012|title=Matt Bentley|access-date=October 27, 2011|publisher=Canadian Online Explorer|work=Slam! Sports}}

{{Professional wrestling sidebar}}

Hickenbottom began to train under Mexican professional wrestler Jose Lothario.{{cite web |last=Roopansingh |first=Jaya |date=March 14, 2004 |title=Shawn Michaels, still the show-stopper |url=http://slam.canoe.com/Slam/Wrestling/Wrestlemania20/2004/03/14/381421.html |access-date=March 29, 2008 |work=Slam! Sports |publisher=Canadian Online Explorer|url-status=dead|archive-url=https://web.archive.org/web/20151223052750/http://slam.canoe.com/Slam/Wrestling/Wrestlemania20/2004/03/14/381421.html|archive-date=December 23, 2015}}{{harv|Michaels|Feigenbaum|2005|p=57}} During his training, Hickenbottom adopted the ring name, "Shawn Michaels". After his training with Lothario, he debuted as Shawn Michaels with the National Wrestling Alliance's (NWA) Mid-South Wrestling territory on October 16, 1984, against Art Crews, losing to Crews via swinging neckbreaker. Michaels's performance in his debut match impressed many veterans, including Terry Taylor. Michaels made his televised debut on October 20, 1984, teaming with Jim Hornet in a losing effort against the tag team of Hercules Hernandez and "Dr. Death" Steve Williams.{{Cite web |date=October 20, 2021 |title=On October 20, 1984 Shawn Michaels made his television debut in a match with Mid-South Wrestling as he and Jim Horner took on Hercules Hernandez and "Dr. Death" Steve Williams. Michaels had made his official debut with the Mid-South Wrestling territory on October 16, against Art Crews, losing to Crews via swinging neckbreaker. |url=https://www.facebook.com/Davenportsportsnetwork/videos/on-october-20-1984-shawn-michaels-made-his-television-debut-in-a-match-with-mid-/3155843098075906/ |access-date=September 9, 2023 |website=Facebook}}

In January 1985, he debuted for World Class Championship Wrestling (WCCW), the NWA territory in Dallas, Texas. In April 1985, Michaels went to work for another NWA territory in Kansas City called Central States Wrestling.{{Harv|Michaels|Feigenbaum|2005|pp=75–77}} There, he and tag team partner Marty Jannetty defeated The Batten Twins for the NWA Central States Tag Team Championship, later losing it back to the Battens.

After leaving Kansas City, he returned to Texas to wrestle for Texas All-Star Wrestling (TASW).{{cite video|date=2007|title=The Shawn Michaels Story: Heartbreak & Triumph|medium=DVD|publisher=WWE Home Video}} During his time with TASW, Michaels replaced Nick Kiniski in the American Breed tag team, teaming with Paul Diamond. Michaels and Diamond were awarded the TASW Tag Team Championship by Chavo Guerrero Sr. The team was later renamed American Force.{{harv|Michaels|Feigenbaum|2005|p=88}} While in TASW, Michaels and Diamond feuded with Japanese Force.{{citation needed|date=September 2024}}

Image:The Rockers, 1987.jpg in 1987, known together as "the (Midnight) Rockers" during their time as AWA World Tag Team Champions]]

Michaels made his national-level debut, as Sean Michaels, at the age of 20 in the American Wrestling Association (AWA), in a victory over Buddhakhan on ESPN. He was once again teamed with Marty Jannetty, billed as The Midnight Rockers. The Midnight Rockers won the AWA World Tag Team Championship, defeating Doug Somers and Buddy Rose.

In 1987, The Rockers were signed by a competing promotion: the World Wrestling Federation (WWF). They were fired from WWF two weeks later, for a bar incident (a misunderstanding, according to Michaels's autobiography). They then returned to AWA, where they won the AWA tag team titles for a second time, but were re-signed by WWF a year later.{{Harv|Michaels|Feigenbaum|2005|pp=116–118}}

{{Main|The Rockers}}

The Rockers redebuted at a WWF live event on July 7, 1988.{{Harv|Michaels|Feigenbaum|2005|p=133}} Due to WWF chairman Vince McMahon's desire to have his performers carry WWF-exclusive ring names, Michaels and Jannetty were renamed, as simply The Rockers. The team proved popular with both children and women and was a mid-card stalwart of television and pay-per-view shows for the next two years.{{Harv|Michaels|Feigenbaum|2005|pp=148–150}} During this time, Michaels headlined his first pay-per-view for the WWF when The Rockers were involved in the 4-on-4 Survivor Series match main event of Survivor Series on November 23, 1989, which they won.[http://www.thehistoryofwwe.com/89.htm Survivor Series 89 – Chicago, IL – Rosemont Horizon – November 23, 1989]. The History of WWE. Retrieved August 15, 2012.

On October 30, 1990, The Rockers unofficially won the WWF Tag Team Championship from The Hart Foundation (Bret Hart and Jim Neidhart), as Neidhart, half of the championship team, was in the process of negotiating his release from the company. The match was taped with The Rockers winning the title, but soon after Neidhart came to an agreement with management and was rehired. The championship was returned to the Hart Foundation, while the title change was never broadcast or even acknowledged on television (though The Rockers did have a successful title defense on November 3, 1990, against Power and Glory (Hercules and Paul Roma) before the title was returned to the Hart Foundation). When news spread, WWF explained that the original result was void due to a collapsed turnbuckle in the ring during the bout. A buckle had indeed broken, but not to a noticeable or dangerous extent during the match. The Rockers continued their partnership, eventually splitting on December 2, 1991, aired January 11, 1992, on Wrestling Challenge, during an incident on Brutus Beefcake's televised Barber Shop talk show promotional segment.{{Harv|Michaels|Feigenbaum|2005|pp=157–159}} Michaels superkicked Jannetty and threw him through a glass window on the set of Beefcake's talk show.{{cite web|url=http://sports.ign.com/articles/583/583410p1.html|title=IGN: Shawn Michaels Interview|last=Robinson|first=Jon|date=January 28, 2005|publisher=News Corporation|work=IGN Sports|access-date=August 6, 2008}} Jannetty returned to the WWF the following year and enjoyed moderate success before leaving the company in 1994, while Michaels became a prominent villain of the early to mid-1990s as "The Boy Toy".

{{See also|Two Dudes with Attitudes}}

At the suggestion of Curt Hennig, Michaels adopted the nickname "The Heartbreak Kid". Along with his new name came a new gimmick as a vain, cocky villain.{{cite journal|first=Steve|last=Anderson|title=7 Superstars Shining Brightly|journal=Wrestling Digest|date=February 2001}} He was put together with mirror-carrying manager, Sensational Sherri, who according to the storyline had become infatuated with him. Sherri even sang the first version of his new theme music, "Sexy Boy". During that period, after Michaels had wrestled his scheduled match at live events, his departure was announced with "Shawn Michaels has left the building", alluding to the phrase "Elvis has left the building".{{Harv|Michaels|Feigenbaum|2005|pp=165–166}}

File:Shawn and Diesel tag champs.jpg acted as Michaels's on-air bodyguard and tag team partner for two championship reigns.]]

At WrestleMania VIII on April 5, 1992, Michaels defeated Tito Santana in his first pay-per-view singles match after both men had simultaneously eliminated each other from that year's Royal Rumble.[http://www.wwe.com/shows/wrestlemania/8/results WrestleMania VIII: Full Event Results]. WWE. Retrieved June 14, 2011. Michaels subsequently became a contender to the promotion's singles titles and failed to win the WWF Championship from champion Randy Savage in his first opportunity to compete for that title at British event UK Rampage, held on April 19 at the Sheffield Arena and broadcast on Sky Movies Plus[http://www.prowrestlinghistory.com/supercards/usa/wwf/wwfuk.html#ramp92 UK Rampage 1992]. Pro Wrestling History. Retrieved May 30, 2011. (the match later aired in the US on the edition of June 15 of Prime Time Wrestling).[http://www.thehistoryofwwe.com/92.htm UK Rampage 92 – Sheffield, England – Arena – April 19, 1992]. The History of WWE. Retrieved January 27, 2015. Michaels was also unable to win the Intercontinental Championship from Bret Hart in the WWF's first ladder match at a Wrestling Challenge taping on July 21, which was subsequently made available on multiple Coliseum/WWE Home Video releases.[http://www.thehistoryofwwe.com/92.htm WWF @ Portland, ME – Civic Center – July 21, 1992]. The History of WWE. Retrieved May 30, 2011.{{Harv|Michaels|Feigenbaum|2005|pp=161–162}} However, he won the title from The British Bulldog on Saturday Night's Main Event XXXI, which aired on November 14.{{cite web|url=http://www.wwe.com/inside/titlehistory/intercontinental/|title=Title History: Intercontinental|access-date=July 17, 2008|publisher=World Wrestling Entertainment}} He faced Hart for the WWF Championship at Survivor Series on November 25, but lost the match.{{cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year= 2007|pages=90–91}} Originally the secondary main event, Michaels and Hart became the primary main event after The Ultimate Warrior was unable to compete and was replaced by Mr. Perfect (Curt Hennig) in the tag team match that involved Randy Savage against the team of Ric Flair and Razor Ramon.{{cite book|title=Wrestlecrap: The Very Worst of Pro Wrestling|last=Baer|first=Randy|author2=Reynolds, R.D.|publisher=ECW Press|year=2003|isbn=1-55022-584-7|page=[https://archive.org/details/wrestlecrapveryw00rdre/page/74 74]|url=https://archive.org/details/wrestlecrapveryw00rdre/page/74}} During this time, Michaels and Sherri split and he engaged himself in a feud with former tag team partner Marty Jannetty. Michaels lost the Intercontinental Championship to Jannetty on the May 17, 1993, episode of Raw, but regained it on June 6 with the help of his debuting "bodyguard" (and off-air friend) Diesel.

In September 1993, Michaels was suspended for testing positive for steroid – a charge he never admitted.{{Harv|Michaels|Feigenbaum|2005|p=182}} On WWF programs, his suspension was explained by his having neglected to defend the title often enough. After turning down World Championship Wrestling (WCW)'s advances, Michaels returned to the WWF and made several appearances in the United States Wrestling Association (USWA) during a WWF/USWA cross-promotion. He returned on November 24 at Survivor Series, substituting for Jerry Lawler, who was dealing with legal issues, in a match pitting himself and three of Lawler's "Knights" against the Hart brothers, Bret, Bruce, Keith and Owen.{{cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|pages=91–92}}

File:Shawn Michaels in 1994.jpg

In 1994, Michaels entered a rivalry with Razor Ramon, who had won the vacant Intercontinental Championship during Michaels's absence.{{Harv|Michaels|Feigenbaum|2005|pp=182–187}} Since Michaels had never been defeated in the ring for the title, he claimed to be the rightful champion and even carried around his old title belt. This feud culminated in a ladder match between the two on March 20 at WrestleMania X. Michaels lost the match, which featured both his and Ramon's championship belts suspended above a ladder in the ring. This match was voted by fans as "Match of the Year" by Pro Wrestling Illustrated. It also received a five-star rating from Wrestling Observer Newsletter editor Dave Meltzer, the first of nine WWF/E matches to do so. Over the next few months, Michaels battled various injuries and launched the Heartbreak Hotel television talk show segment, mainly shown on Superstars.{{Harv|Michaels|Feigenbaum|2005|p=190}}

On August 28, Michaels and Diesel won the WWF Tag Team Championship from The Headshrinkers (Samu and Fatu).{{Harv|Michaels|Feigenbaum|2005|p=195}} The next day at SummerSlam, Diesel lost the Intercontinental Championship to Ramon when Michaels accidentally superkicked Diesel. This triggered a split between the two, a storyline that was drawn out until Survivor Series on November 24.{{cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|pages=92–93}} Michaels won the Royal Rumble on January 22, 1995,{{Harv|Michaels|Feigenbaum|2005|pp=196–199}} which set up a championship grudge match on April 2 at WrestleMania XI against Diesel (who had gone on to win the WWF Championship from Bob Backlund). As part of the storyline, Michaels recruited Sid as his bodyguard for the build-up, lost the match{{cite news|last=Martin|first=Finn|title=Power Slam Magazine, issue 10|work=Tough luck Shawn (WrestleMania XI)|publisher=SW Publishing|date=April 24, 1995|pages=20–25}} and was attacked by Sid the following night.{{Harv|Michaels|Feigenbaum|2005|p=204}} This would result in him becoming a fan favorite.{{Harv|Michaels|Feigenbaum|2005|pp=203–204}} After this, Michaels took time off

{{Main|The Kliq}}

Michaels returned to the ring as a fan favorite in May 1995 and defeated Jeff Jarrett to win his third Intercontinental Championship on July 24 at In Your House 2: The Lumberjacks.{{Harv|Michaels|Feigenbaum|2005|p=209}} This led to a title defense against Razor Ramon on August 27 at SummerSlam in a ladder match, which Michaels won. Around this time, Michaels became the leader of a backstage group known as The Kliq. Critics perceive the group to have sufficient clout with WWF owner Vince McMahon, becoming dominant wrestling figures in the WWF for several years in the mid-1990s, causing friction with other wrestlers. Michaels disputes the perception, saying that McMahon pushed only deserving wrestlers.{{Harv|Michaels|Feigenbaum|2005|pp=206–208}} Michaels's fan base was later nicknamed "The Kliq" as an inside reference to the real "Kliq".{{Harv|Michaels|Feigenbaum|2005|p=230}} In October 1995, Michaels was the victim of a legit assault outside a bar in Syracuse, New York. Due to not being able to compete, Michaels was forced to forfeit the Intercontinental Championship to his original opponent Dean Douglas on October 22 at In Your House: Great White North,{{Harv|Michaels|Feigenbaum|2005|p=213}} who in turn Douglas lost the championship to Razor Ramon, another member of the Kliq.{{cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|page=94}} During a match with Owen Hart on a November episode of Raw, Hart performed an enzuigiri that struck the back of Michaels's head.{{Harv|Michaels|Feigenbaum|2005|p=215}} They continued the match, but Michaels collapsed in the ring, supposedly because he had suffered a concussion. The concussion was scripted, which was kept from most fans at the time. A retirement angle was written so that Michaels could take some time off after he came back from an injury too soon.

{{Main|D-Generation X}}

After teasing retirement, Michaels returned to the WWF at the Royal Rumble match on January 21, 1996, winning for the second year in a row to receive a WWF Championship match in the main event at WrestleMania XII.{{cite news |title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|page=95}} Around this time, Jose Lothario became Michaels's on-screen manager.{{Harv|Michaels|Feigenbaum|2005|p=219}} At WrestleMania XII on March 31, Michaels defeated WWF Champion Bret Hart in the overtime of their sixty-minute Iron Man match, which had ended in a scoreless tie. On May 19, Michaels and his fellow Kliq members were involved in the incident known as "Curtain Call". Diesel and Razor Ramon were about to leave WWF to company rival WCW. After Michaels won a match against Diesel, Ramon and Hunter Hearst Helmsley came to the ring and joined Michaels and Diesel in a group-hug.{{harv|Assael|Mooneyham|2002|p=156}} As Diesel and Helmsley were seen as villains at the time, in contrast to Michaels and Ramon, this constituted a breach of "kayfabe", as acting out of character, which was rare and controversial at the time. As WCW gained momentum due to the signings of Hall and Nash, Michaels held the championship for most of the year. At Survivor Series on November 17, Michaels lost the WWF Championship to Sycho Sid{{Harv|Michaels|Feigenbaum|2005|p=234}} but recaptured the title on January 19, 1997, at Royal Rumble.{{cite web|url=http://www.wwe.com/inside/titlehistory/wwechampionship/304454115|title=HBK's second WWE title reign|publisher=World Wrestling Entertainment|access-date=August 25, 2009|archive-date=February 11, 2012|archive-url=https://web.archive.org/web/20120211041505/http://www.wwe.com/inside/titlehistory/wwechampionship/304454115|url-status=dead}}

On a special episode of Raw dubbed Thursday Raw Thursday, Michaels vacated the WWF Championship. He explained to fans that he was informed by doctors that he had suffered a knee injury. Michaels contemplated thoughts of retirement and stated that he "had to find his smile again", which he had "lost" somewhere down the line.{{Harv|Michaels|Feigenbaum|2005|pp=239–240}} After consulting with Dr. James Andrews, who concluded that he did not need surgery, Michaels underwent four weeks of physical therapy and returned to in-ring action a few months later, briefly teaming with Stone Cold Steve Austin to win the WWF Tag Team Championship.{{cite web|url=http://www.wwe.com/inside/titlehistory/worldtagteam/304454132122112|title=Stone Cold & Shawn Michaels first World Tag Team title reign|access-date=July 12, 2007|publisher=World Wrestling Entertainment|archive-date=August 27, 2011|archive-url=https://web.archive.org/web/20110827143219/http://www.wwe.com/inside/titlehistory/worldtagteam/304454132122112|url-status=dead}} In his autobiography, Michaels discusses his real-life feud with Bret Hart, claiming that Hart did interviews on live television claiming that Michaels was faking his whole injury.{{Harv|Michaels|Feigenbaum|2005|pp=243–244}}

File:WWE- Birmingham 200997 (22).jpg

By the spring of 1997, the real-life backstage conflict between Michaels and Hart was reaching its height. Both men were going out on television and frequently making personal, true to heart remarks about one another. Michaels briefly left the WWF in June of that year after a real backstage fight with Hart, just hours before a Raw Is War show, which allegedly resulted from Michaels making an on-air remark, known as the "Sunny Days" comment, implying that Hart (who was married at the time) was having an affair with Tammy Sytch, a manager and valet who was signed to the WWF as Sunny. Michaels and Austin were still WWF Tag Team Champions at the time during an ongoing feud with the Hart Foundation and a tournament was made to decide new tag team champions. Michaels eventually returned that summer in July. At SummerSlam on August 3, Michaels officiated the WWF Championship match between WWF Champion The Undertaker and Bret Hart.{{Harv|Michaels|Feigenbaum|2005|pp=247–249}} The match ended controversially, with Michaels hitting The Undertaker with a chair (unintentionally, as he was aiming for Hart after he spat in his face). Michaels was then forced to award the championship to his nemesis, Bret Hart. The next night on Raw Is War, signs of a heel turn started to show as Michaels told the WWF fans what happened at SummerSlam was an accident and that he dealt with The Undertaker when the time came. At WWF One Night Only, held in Birmingham, England, on September 20, Michaels defeated The British Bulldog to capture the WWF European Championship.{{cite web |title=HBK's first European title reign |url=http://www.wwe.com/inside/titlehistory/euro/358418 |url-status=dead |archive-url=https://web.archive.org/web/20080224000439/http://www.wwe.com/inside/titlehistory/euro/358418 |archive-date=February 24, 2008 |access-date=July 11, 2007 |publisher=World Wrestling Entertainment}} The fans at the event were so upset at the result of the match they booed Michaels out of the building to the extent that they littered the ring with garbage, cementing his second heel turn.{{cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|pages=99–100}} With this win, Michaels became the first Grand Slam Champion. At In Your House: Badd Blood on October 5, Michaels defeated The Undertaker in the first Hell in a Cell match, during which Michaels fell off the side of the {{convert|15|ft|m|0|adj=on|disp=flip}} high structure through a table.{{Harv|Michaels|Feigenbaum|2005|pp=257–259}} The match received a 5-star rating from Dave Meltzer.{{cite web|url=https://www.thesportster.com/wwe-every-undertaker-vs-shawn-michaels-match-reviewed/|title=Every Undertaker Vs. Shawn Michaels Match, Definitely Reviewed|last=Kelly|first=Andrew|work=The Sportster|date=18 May 2024|access-date=20 January 2025}}

In the fall, Michaels joined forces with real-life friend Hunter Hearst Helmsley (later known as Triple H), Helmsley's then real-life girlfriend Chyna, and Rick Rude to form the stable D-Generation X (DX).{{Harv|Michaels|Feigenbaum|2005|p=252}} Michaels continued his rivalry with Bret Hart and his reformed Hart Foundation, which was now a pro-Canada stable. Michaels taunted the group and Canada by engaging in acts such as blowing his nose with and humping the Canadian Flag. Michaels later claimed the flag desecration was Hart's idea.{{Harv|Michaels|Feigenbaum|2005|pp=274–275}} Michaels's feud with the Hart Foundation culminated in a WWF Championship match at Survivor Series on November 9 against Hart. Michaels came out of this match, dubbed by fans the "Montreal Screwjob", as the WWF Champion.{{cite web|url=http://www.wwe.com/inside/titlehistory/wwechampionship/30445415 |title=HBK's third WWE title reign |access-date=July 13, 2007 |publisher=World Wrestling Entertainment |url-status=dead |archive-url=https://web.archive.org/web/20080105072205/http://www.wwe.com/inside/titlehistory/wwechampionship/30445415 |archive-date=January 5, 2008}} Michaels now held both the WWF and European championships at the same time. Michaels dropped the European Championship to DX member Hunter Hearst Hemsley in a farcical match.{{cite web|url=http://www.wwe.com/inside/titlehistory/euro/|title=Title History: European|access-date=July 16, 2008|publisher=World Wrestling Entertainment}}

On January 18, 1998, at the Royal Rumble, in a casket match against The Undertaker, Michaels took a back body drop to the outside of the ring and hit his lower back on the casket, causing him to herniate two discs and crush one completely.{{Harv|Michaels|Feigenbaum|2005|p=283}} Michaels went on to win the match but the injury rendered him unable to compete on the following month's No Way Out of Texas: In Your House as advertised, and forced him into retirement a night after losing the WWF Championship to Stone Cold Steve Austin on March 29 at WrestleMania XIV.{{Harv|Assael|Mooneyham|2002|p=202}}

After being away for nearly four months, Michaels made a surprise return to the WWF as a guest commentator on the July 13 episode of Raw Is War. Michaels continued to make non-wrestling appearances on WWF programming and on November 23 he replaced Sgt. Slaughter as the WWF Commissioner, eventually joining Vince McMahon's group of wrestlers called The Corporation.{{cite episode|title=Raw is War|series-link=WWE Raw|series=WWE Raw|network=USA Network|airdate=November 23, 1998|season=6|number=47}} Throughout late 1998 and early 1999, Michaels made regular television appearances on Raw, in which he scheduled matches, throwing around his authority, and sometimes even deciding the outcome of matches.{{cite episode|title=Raw is War|series-link=WWE Raw|series=WWE Raw|network=USA Network|airdate=November 30, 1998|season=6|number=48}}{{cite episode|title=Raw is War|series-link=WWE Raw|series=WWE Raw|network=USA Network|airdate=December 21, 1998|season=6|number=51}}{{cite episode|title= Raw is War|series-link=WWE Raw|series=WWE Raw|network=USA Network|airdate=December 28, 1998|season=6|number=52}} On the January 4, 1999, episode of Raw Is War, Michaels re-joined DX as a face, but disappeared from WWF television for a few weeks to have back surgery{{cite web|author=Mr. X|title=Foley win Rocks WWF|url=http://slam.canoe.ca/SlamWrestlingArchive/jan9_fol.html|archive-url=https://archive.today/20120714224925/http://slam.canoe.ca/SlamWrestlingArchive/jan9_fol.html|url-status=usurped|archive-date=July 14, 2012|publisher=Canadian Online Explorer|work=Slam! Sports|date=January 9, 1999|access-date=July 17, 2008|quote=Michaels, who brought Degeneration X along with him, was later betrayed by his comrades, when he was locked out of the building and pounded by the corporate thugs. That allows Michaels to be absent {{sic|for a|while|expected=for a while}} and he'll have back surgery.}} and by the time he returned DX was on the way of dissolving within the next couple of months.{{citation needed|date=September 2024}}

On November 23, 1999, Michaels made a special appearance for Frontier Martial-Arts Wrestling at the 10th Anniversary Show at the Yokohama Arena, serving as the guest referee for the H vs fake Hayabusa (Mr. Gannosuke) main event. He got involved in the match when Gannosuke delivered a low blow on him and he responded later on with Sweet Chin Music.{{cite web|url=http://fmwwrestling.us/FMWHistory3.html|title=FMW History Part 3|publisher=FMW World|access-date=March 25, 2013}}

Michaels made occasional appearances as the WWF Commissioner during the spring and summer of 1999, but remained absent from television after August until May 15, 2000, when he returned on Raw Is War to declare himself the special guest referee for The Rock and Triple H's Iron Man match at Judgment Day.{{cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|page=106}} One month later, Michaels briefly reappeared on Raw Is War to hand over the role of Commissioner to Mick Foley, and after another appearance in October did not make any in-arena appearances until mid-2002.{{cite episode|title=Raw is War|series-link=WWE Raw|series=WWE Raw|network=USA Network|airdate=June 26, 2000|season=8|number=26}} He appeared briefly on television to make a speech at WWF New York during Armageddon on December 10, 2000.{{cite web|first=John|last=Powell|url=http://www.canoe.com/SlamWrestlingPPV/dec11_wwfarm-can.html|title=Armageddon: WWF saves the worst for last|access-date=March 25, 2011|date=December 11, 2000|publisher=Canadian Online Explorer|work=Slam! Sports|url-status=dead|archive-url=https://web.archive.org/web/20010624185059/http://www.canoe.com/SlamWrestlingPPV/dec11_wwfarm-can.html|archive-date=June 24, 2001}}

On April 4, 2000, Michaels returned to wrestling for a one-night appearance defeating Paul Diamond in a bunkhouse brawl at Texas Wrestling Entertainment.{{cite web |title=Events Database - Texas Wrestling Entertainment|url=https://www.cagematch.net/?id=2&nr=796&page=4&year=2000&promotion=110|website=Cage Match |access-date=January 12, 2024|quote=4.4.2000}}{{Cite web |title=SHAWN MICHAELS' CAREER ENDING BACK INJURY IN 1998, THE MINOTAUR & ARACHNIMAN IN WCW AND MORE {{!}} PWInsider.com |url=https://www.pwinsider.com/article/187403/shawn-michaels-career-ending-back-injury-in-1998-the-minotaur-arachniman-in-wcw-and-more.html?p=1 |access-date=2024-09-11 |website=www.pwinsider.com}}

Believing that his wrestling career was over, Michaels was interested in training individuals who wanted to become professional wrestlers.{{Harv|Michaels|Feigenbaum|2005|pp=299–302}} He saw potential in using his name and opened the Shawn Michaels Wrestling Academy (later the Texas Wrestling Academy) in 1999, after his lawyer Skip McCormick suggested the idea. Michaels left the academy in 2002, giving co-founder Rudy Boy Gonzalez sole responsibility due to Michaels's new contract with WWE. Michaels was also a sportscaster for San Antonio's local news for a short period during his retirement.

On the June 3, 2002 episode of Raw, Michaels returned to WWE television after 18 months of absence when Kevin Nash announced him as a new member of the recently reformed New World Order (nWo). Michaels was the only nWo member to have never worked in WCW.{{cite book|first=Michael|last=McAvennie|title=WWE The Yearbook: 2003 Edition|publisher=WWE Books|date=April 2003|isbn=0-7434-6373-0|pages=140–141|quote=The Black and White seemed complete after Kevin Nash announced the New World Order's latest recruitment at the June 3 Raw: the king of WWE "Attitude," Shawn Michaels!}} After the nWo had disbanded, Triple H appeared to make amends with Michaels. This was solidified when Michaels pleaded Triple H to return to Raw. Later on, they came down to the ring sporting their DX music and attire. When the pair was about to perform their trademark "Suck It" taunt, Triple H turned on Michaels by performing a Pedigree on him.{{cite web|url=http://www.wrestleview.com/results/raw/83.shtml|title=WWE Raw Results – July 22, 2002|first=Adam|last=Martin|access-date=July 17, 2008|date=July 22, 2002|publisher=WrestleView.com}} Continuing the angle, in his first WWE match since WrestleMania XIV, Michaels defeated Triple H at SummerSlam on August 25, but was attacked by Triple H with a sledgehammer after the match.{{cite book|first=Michael|last=McAvennie| title=WWE The Yearbook: 2003 Edition|publisher=WWE Books|date=April 2003|isbn=0-7434-6373-0|page=212}} At Survivor Series on November 17, Michaels won the World Heavyweight Championship from Triple H in the first Elimination Chamber match.{{cite book|first=Michael|last=McAvennie|title=WWE The Yearbook: 2003 Edition|publisher=WWE Books|date=April 2003|isbn=0-7434-6373-0|page=314}} On December 15 at Armageddon, he lost the championship to Triple H in a Three Stages of Hell match.{{cite book|first=Michael|last=McAvennie|title=WWE The Yearbook: 2003 Edition|publisher=WWE Books|date=April 2003|isbn=0-7434-6373-0|page=330}}

Image:Jerichomichaels.jpg at WrestleMania XIX in March 2003 was his first match at a WrestleMania event since WrestleMania XIV in March 1998.]]

Michaels then began a rivalry with Chris Jericho, after Jericho claimed that he was the next Shawn Michaels.{{cite web|url=http://www.wrestleview.com/news/1048567703.shtml|title=Full WWE Raw Results – 3/24/03|last=Moore|first=Wesley|date=March 24, 2003| publisher=WrestleView.com|access-date=September 15, 2008}} On the January 13, 2003 episode of Raw, after Jericho won a battle royal to select his entry number for the Royal Rumble match, choosing number two in order to start the match with Michaels,{{cite web|first=Michael|last=Barrett|url=http://www.wrestleview.com/news/1042517288.shtml|title=WWE Raw Results – January 13, 2003|access-date=July 17, 2008|date=January 13, 2003|publisher=WrestleView.com}} who had already been named number one. At the Royal Rumble on January 19, Jericho, with the help of Christian, eliminated Michaels. Michaels later interfered in the match, causing Jericho to be eliminated.{{cite news|last= Hurley|first=Oliver|title=Power Slam Magazine, issue 104|work=Every Man for himself (Royal Rumble 2003)|publisher=SW Publishing| date=February 21, 2003|pages=16–19}} Michaels defeated Jericho on March 30 at WrestleMania XIX but was low-blowed after hugging Jericho.{{cite web|url=http://slam.canoe.ca/Slam/Wrestling/2003/03/31/55003.html|archive-url=https://archive.today/20120721000346/http://slam.canoe.ca/Slam/Wrestling/2003/03/31/55003.html|url-status=usurped|archive-date=July 21, 2012|title=WWE shines at WrestleMania XIX|first=John|last=Powell|access-date=June 13, 2008|date=March 31, 2003|publisher=Canadian Online Explorer|work=Slam! Sports}}

At Backlash on April 27, Michaels lost to the team of Jericho, Triple H and Ric Flair in a 6-man tag team. This led to a match between Michaels and Flair at Bad Blood on June 15, which Flair won. Following this, Michaels continued feuding with the members of Triple H's faction Evolution. He was unsuccessful in capturing the World Heavyweight Championship at SummerSlam on August 24 with Triple H retaining in the second Elimination Chamber match. He then lost to Randy Orton at Unforgiven on September 21. At Armageddon on December 14, Michaels defeated the group's enforcer Batista.{{cite web|url=https://www.thesportster.com/every-major-shawn-michaels-feud-rivalry-wwe-comeback-ranked-worst-best/|title=Every Major Shawn Michaels Feud Of His WWE Comeback, Ranked|last=King|first=Trevor|work=The Sportster|date=25 February 2023|access-date=20 January 2025}}

On the December 29 episode of Raw, Michaels seemingly defeated Triple H after a Sweet Chin Music for the World Heavyweight Championship in his hometown of San Antonio, Texas, with Eric Bischoff as the special guest referee (Earl Hebner originally refereed the match, only to be knocked out by Triple H in the middle of the match). However, Bischoff reversed the decision due to both men's shoulders being on the mat. Angered by this, Michaels attacked Ric Flair and Bischoff. He was subsequently fired by Bischoff but rehired by Stone Cold Steve Austin.{{Cite web |last=Greenslade |first=Mike |date=December 30, 2003 |title=WWE Raw Results – December 29, 2003 |url=https://www.wrestleview.com/results/raw/raw2003/1072765329.shtml |access-date=January 26, 2023 |publisher=WrestleView.com}}

As a part of an ongoing feud with Triple H, the two competed alongside Chris Benoit in the main event on March 14, 2004, at WrestleMania XX for the World Heavyweight Championship, which Benoit won.{{cite news|title=2007 Wrestling Almanac & Book of Dacts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|page=115}} The night before this, Michaels inducted Tito Santana in the WWE Hall of Fame. A triple threat WrestleMania rematch for the title took place on April 18 at Backlash, where Benoit successfully retained it after forcing Michaels to submit to a Sharpshooter.{{cite web |last=Martin |first=Adam |date=April 18, 2004 |title=Full WWE Backlash (Raw) PPV Results – 4/18/04 from Edmonton, Alberta, CA |url=http://www.wrestleview.com/news2004/1082342965.shtml |url-status=live |archive-url=https://web.archive.org/web/20080207231011/http://www.wrestleview.com/news2004/1082342965.shtml |archive-date=February 7, 2008 |access-date=February 15, 2008 |publisher=WrestleView.com}} Due to the "Montreal Screwjob" incident, the Edmonton crowd booed Michaels, with chants of "You screwed Bret!" being heard during his match at Backlash.{{cite web|first=John|last=Powell|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2004/04/19/427888.html|archive-url=https://archive.today/20120630080531/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2004/04/19/427888.html|url-status=usurped|archive-date=June 30, 2012|title=Feature bouts save Backlash|access-date=February 6, 2008|date=April 19, 2004|work=Slam! Sports|publisher=Canadian Online Explorer}} At Bad Blood on June 13, Michaels lost to Triple H in the longest Hell in a Cell match in history. Four months later, he lost a World Heavyweight Championship match against Triple H, after Edge interfered on October 19 at Taboo Tuesday, when the fans voted for him ahead of Edge and Chris Benoit to face Triple H one more time.{{cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|page=116}} Following this, Michaels was out of action for a few months with a legit torn meniscus.{{Harv|Michaels|Feigenbaum|2005|p=333}}

{{See also|D-Generation X#Shawn Michaels and Triple H (2006–present)|l1=D-Generation X reunion}}

At the Royal Rumble on January 30, 2005, after losing to Edge, Michaels competed in the Royal Rumble match and eliminated Kurt Angle. In seeking revenge, Angle re-entered the ring and eliminated Michaels, and thus placed him in an ankle lock submission hold, outside the ring.{{cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|page=117}} Michaels issued a challenge to Angle for a match at WrestleMania 21, which Angle accepted when he appeared on Raw to attack Michaels.{{cite web |date=February 28, 2005 |title=Dream match made |url=http://www.wrestleview.com/results/raw/raw2005/1109657210.shtml |access-date=July 17, 2008 |publisher=WrestleView.com}} The following week on Raw, Marty Jannetty and Michaels had a one time reunion as The Rockers and defeated La Résistance (Robért Conway and Sylvain Grenier).{{cite web|first=Hunter|last=Golden|url= http://www.wrestleview.com/results/raw/raw2005/1110863071.shtml|title=WWE Raw Results – March 14, 2005|access-date=July 17, 2008|date=March 14, 2005|publisher=WrestleView.com}} Three days later on SmackDown!, Angle defeated Jannetty, after Angle made Jannetty submit to the ankle lock.{{cite web|first=L. Anne|last=Carrington|url= http://www.wrestleview.com/results/smackdown/smackdown2005/1111123561.shtml|title=WWE SmackDown Results – March 17, 2005|access-date =July 17, 2008|date=March 17, 2005|publisher=WrestleView.com}} To send a "message" to Michaels, Angle also humiliated Michaels's former manager, Sensational Sherri, when he applied the ankle lock hold on her.{{cite web|first=L. Anne|last=Carrington|url= http://www.wrestleview.com/results/smackdown/smackdown2005/1111728681.shtml|title=WWE SmackDown Results – March 24, 2005|access-date =July 17, 2008|date=March 24, 2005|publisher=WrestleView.com}} At WrestleMania on April 3, Angle defeated Michaels by submission, again with an ankle lock.

{{multiple image

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The next night on Raw, Muhammad Hassan and Daivari came out to confront and assault Michaels.{{cite web|first=Paul|last=Nemer|url=http://www.wrestleview.com/results/raw/raw2005/1112670613.shtml|title=WWE Raw Results – April 4, 2005|access-date=July 17, 2008|date=April 4, 2005|publisher=WrestleView.com}} On the April 11 episode of Raw, Michaels approached General Manager Eric Bischoff, in which he demanded a handicap match with Hassan and Daivari. Bischoff refused to schedule such a match and instead told Michaels to find a partner. Michaels then made a plea for Hulk Hogan to come back and team with him.{{cite web|first=Hunter|last=Golden|url= http://www.wrestleview.com/results/raw/raw2005/1113279748.shtml|title=WWE Raw Results – April 11, 2005|access-date=July 17, 2008|date=April 11, 2005|publisher=WrestleView.com}} On the April 18 episode of Raw, Hassan again led an attack on Michaels until Hogan appeared to save Michaels and accept his offer.{{cite web|first=Hunter|last=Golden|url=http://www.wrestleview.com/results/raw/raw2005/1113883992.shtml|title=WWE Raw Results – April 18, 2005|access-date=July 17, 2008|date=April 18, 2005|publisher= WrestleView.com}} At Backlash on May 1, Hogan and Michaels defeated Hassan and Daivari.{{cite web|url=http://www.wwe.com/shows/backlash/history/backlash2005/results/ |title=WWE Backlash 2005 results |publisher=World Wrestling Entertainment |access-date=July 16, 2008 |url-status=dead |archive-url=https://web.archive.org/web/20071112123041/http://www.wwe.com/shows/backlash/history/backlash2005/results/ |archive-date=November 12, 2007}} Later, in a WrestleMania rematch, Michaels defeated Kurt Angle (who was drafted to Raw in the draft lottery) on June 26 at Vengeance.{{cite web|first=Chris|last=Sokol|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2005/06/27/1106996.html|archive-url=https://archive.today/20120718045558/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2005/06/27/1106996.html|url-status=usurped|archive-date=July 18, 2012|title=Batista retains with a Vengeance|access-date=February 3, 2011|date=June 27, 2005|publisher=Canadian Online Explorer|work=Slam! Sports}} On the July 4 episode of Raw, after defeating Carlito and Kurt Angle, Michaels hit Hogan with his Sweet Chin Music, knocking Hogan to the ground and turning heel for the first time since 1998.{{cite web|first=Hunter|last=Golden|url=http://www.wrestleview.com/results/raw/raw2005/1120520901.shtml|title=WWE Raw Results – July 4, 2005|access-date=July 17, 2008|date=July 4, 2005|publisher=WrestleView.com}} The following week on Raw, Michaels appeared on Piper's Pit where he superkicked Roddy Piper and then challenged Hogan to a match at SummerSlam, which Hogan accepted the following week.{{cite web|url=http://www.wrestleview.com/results/raw/raw2005/1121140355.shtml|title=Raw Results – July 11, 2005|last=Golden|first=Hunter|date=July 11, 2005|publisher=WrestleView.com|access-date=August 4, 2008}}{{cite web|first=Hunter|last=Golden|url=http://www.wrestleview.com/results/raw/raw2005/1121745844.shtml|title=WWE Raw Results – July 18, 2005|access-date=July 17, 2008|date= July 18, 2005|publisher=WrestleView.com}} Hogan defeated Michaels at SummerSlam on August 21, and after the match Michaels extended his hand to him, saying "I needed to know, and I found out" and he and Hogan shook hands. Michaels left the ring to allow Hogan to celebrate with the crowd, turning face once again.{{cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|page=118}} He became the first person to cleanly defeat Chris Masters on September 18 at Unforgiven with Sweet Chin Music.{{Cite web |last=Sokol |first=Chris |date=September 19, 2005 |title=Unforgiven marred by unfortunate ending |url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2005/09/19/1223557.html |url-status=usurped |archive-url=https://archive.today/20120630080516/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2005/09/19/1223557.html |archive-date=June 30, 2012 |access-date=January 26, 2023 |website=Slam! Sports |publisher=Canadian Online Explorer}} On the October 3 WWE Homecoming episode of Raw, he wrestled old rival Kurt Angle to a 2–2 draw in a 30-Minute Iron Man match. Afterwards, he challenged Angle to sudden-death overtime, but Angle refused and walked out.{{Cite web |last=Golden |first=Hunter |date=October 4, 2005 |title=RAW Results - 10/3/05 - Dallas, TX - (Homecoming to USA Network) |url=https://www.wrestleview.com/results/raw/raw2005/1128399622.shtml |access-date=January 26, 2023 |publisher=WrestleView.com}} He was part of Team Raw at Survivor Series on November 27, but lost the match to Team SmackDown!.{{Cite web |title=Team SmackDown def. Team RAW (Classic Survivor Series Match) |url=https://www.wwe.com/shows/survivorseries/2005/matches/134645811 |access-date=January 26, 2023 |publisher=WWE}}

On the December 26 episode of Raw, Vince McMahon lauded Michaels for his part in the "Montreal Screwjob". Michaels said he was only being loyal to his company, he had moved on, and McMahon should move on as well. McMahon then began setting unusual stipulations for Michaels' matches and interfering on behalf of Michaels' opponents.{{cite web|url=http://www.wwe.com/shows/raw/archive/01022006/|title=The Chamber awaits|access-date=July 16, 2008|date=January 2, 2006|publisher=World Wrestling Entertainment}} On January 29, 2006, at the Royal Rumble, McMahon made his way to the ring, and as Michaels stared at McMahon, Shane McMahon made a surprise appearance to eliminate Michaels.{{cite web|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2006/01/30/1418142.html|archive-url=https://archive.today/20120629143618/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2006/01/30/1418142.html|url-status=usurped|archive-date=June 29, 2012|title=Mysterio claims Rumble; Cena reigns again|last=Plummer|first=Dale|author2=Nick Tylwalk |date=January 30, 2006|work=Slam! Sports|publisher=Canadian Online Explorer|access-date=August 6, 2008}} On the February 13 episode of Raw, McMahon unsuccessfully forced Michaels to sign retirement papers. The following week, Michaels won a handicap match against the Spirit Squad (Kenny, Johnny, Mitch, Nicky and Mikey), after which Michaels's former partner, Marty Jannetty, saved him from the assault by the Spirit Squad. After the two reunited, McMahon offered Jannetty a contract if he "kissed his ass."{{cite web|url=http://www.wwe.com/shows/raw/archive/02202006/|title="Big Time" Pedigree|access-date=July 16, 2008|date=February 20, 2006|publisher=World Wrestling Entertainment}} The following week, Jannetty refused McMahon's offer and instead took Chris Masters's "Masterlock challenge."{{cite web|url=http://www.wwe.com/shows/raw/archive/02272006/|title=Joining the Club|access-date=July 16, 2008|date=February 27, 2006|publisher=World Wrestling Entertainment}} Michaels tried to help Jannetty, which ultimately resulted in Shane attacking Michaels and forcing him to kiss his father's behind. On March 18 at Saturday Night's Main Event XXXII, Shane defeated Michaels in a Street Fight after he applied a sharpshooter on Michaels, leading to McMahon ordering for the bell to be rung though Michaels did not submit, which was an allusion to the "Montreal Screwjob".{{cite news|title=Power Slam Magazine, issue 142|work=Looking at WWE: SNMW (March 18, 2006)|publisher=SW Publishing|date=April 20, 2006|page=25}} Despite interference from the Spirit Squad and Shane, Michaels defeated McMahon on April 2 at WrestleMania 22 in a No Holds Barred match.{{cite video|date=2006|title=WrestleMania 22|medium=DVD|publisher=WWE Home Video}} At Backlash on April 30, The McMahons (Vince and Shane) defeated Michaels and "God" with help from the Spirit Squad in a no disqualification tag team match.{{cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|page=121}} On the May 22 episode of Raw, the Spirit Squad was scripted to injure Michaels's knee.{{cite web|first=Louie|last=Dee|date=May 22, 2006|url=http://www.wwe.com/shows/raw/archive/05222006/|title=Apology Accepted?|access-date=July 16, 2008|publisher=World Wrestling Entertainment}} This angle was written so Michaels could have surgery on his knee, which had been legitimately injured for some time.{{cite journal|title=Injuries shelve Benoit, HBK|date=May 28, 2006|journal=Chicago Sun-Times|page=A70}}

File:D-Generation X.jpg and Michaels as DX in 2006]]In 2006, a series of events took place which suggested a reunion of Michaels and Triple H as DX. They began at WrestleMania 22, where both Michaels and Triple H performed the crotch chop during their matches. On Raw, the two continued to deliver chops, as Michaels feuded with Vince McMahon and Triple H went to challenge John Cena for the WWE Championship, repeatedly butting heads with Vince McMahon in the process. On the June 12 episode of Raw, DX officially reunited. During Triple H's gauntlet match, which had him compete against the Spirit Squad. Michaels came in to help Triple H, and the two did the DX "crotch chops."{{cite web|url=http://www.wrestleview.com/results/raw/raw2006/1150169113.shtml|title=Raw Results – 6/12/06 – Penn State University (DX returns & more)|last=Golden|first=Hunter|date=June 12, 2006|publisher=WrestleView.com|access-date=August 6, 2008}} On June 25 at Vengeance, DX defeated the Spirit Squad in a 5–on–2 handicap match.{{cite web|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2006/06/21/1646013.html|archive-url=https://archive.today/20120714045133/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2006/06/21/1646013.html|url-status=usurped|archive-date=July 14, 2012|title=DX returns with a Vengeance|first=Dale|last=Plummer|author2=Tylwalk, Nick |access-date=July 16, 2008|publisher=Canadian Online Explorer|work=Slam! Sports}} They also defeated the Spirit Squad on July 15 at Saturday Night's Main Event XXXIII in a 5-on-2 elimination match and defeated The McMahons on August 20 at SummerSlam.{{cite web|title=DX beats the odds|first=Jen|last=Hunt|url=http://www.wwe.com/shows/summerslam/history/2006/matches/29444901/results/|access-date=July 13, 2008|date=August 20, 2006|publisher=World Wrestling Entertainment}} At Unforgiven on September 17, DX defeated the McMahons and ECW World Champion The Big Show in a Hell in a Cell match, ending the feud.{{cite web|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2006/09/18/1857195.html|archive-url=https://archive.today/20120714050014/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2006/09/18/1857195.html|url-status=usurped|archive-date=July 14, 2012|title=Unforgiven just averages out|last=Elliott|first=Brian|date=September 18, 2006|work=Slam! Sports|publisher=Canadian Online Explorer|access-date=August 6, 2008}}

At Cyber Sunday on November 5, DX lost to Rated-RKO (Edge and Randy Orton) after fan-selected referee Eric Bischoff allowed the illegal use of a steel chair to give Rated-RKO the ill-gotten win and the plaudit of being the first tag team to defeat DX in a tag team match since their reformation in June 2006.{{cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007|page=122}} On November 26 at Survivor Series, Team DX emerged victorious against Team Rated-RKO in a clean sweep victory.{{cite web|first=Adam|last=Martin|title=Survivor Series Results|url=http://www.wrestleview.com/news2006/1164599352.shtml|publisher=WrestleView.com|access-date=July 16, 2008|date=November 26, 2006}} At New Year's Revolution on January 7, 2007, Triple H suffered a legit torn right quadriceps during their match with Rated-RKO.{{cite web|url=http://www.wwe.com/shows/newyearsrevolution/exclusives/triplehinjury|title=Triple H tears quadriceps tendon|access-date=July 16, 2008|date=January 8, 2007|publisher=World Wrestling Entertainment}} Rated-RKO claimed victory over DX, citing Triple H's injury, as the "end" of DX.{{cite web|first=Noah|last=Starr|url=http://www.wwe.com/shows/raw/archive/01082007/|title=Umaga spikes back|access-date=July 16, 2008|date=January 8, 2007|publisher=World Wrestling Entertainment}} On the January 15 episode of Raw, Michaels lived up to his word of "dealing" with Rated-RKO, from his comments the previous week before,{{cite web|last=Golden|first=Hunter|date=January 8, 2007|url=http://www.wrestleview.com/results/raw/raw2006/1168318587.shtml|title=Raw Results – 1/8/07 – St. Louis, MO – (Fallout from NY Revolution)|access-date=September 21, 2008|publisher=WrestleView.com}}{{cite web|url=http://www.wwe.com/shows/raw/archive/01082007/|title=Umaga spikes back|date=January 8, 2007|last=Starr|first=Noah|publisher=World Wrestling Entertainment|access-date=September 21, 2008}} when he took out Randy Orton with a con-chair-to after a handicap match against Edge and Orton.{{cite web|first=Noah|last=Starr|url=http://www.wwe.com/shows/raw/archive/01152007/|title=DX lives|access-date=July 16, 2008|date=January 15, 2007|publisher=World Wrestling Entertainment}} At the Royal Rumble on January 28, Michaels was the last man eliminated in the Royal Rumble match by the winner of the match, The Undertaker.{{Cite web |last=Dee |first=Louie |date=January 28, 2007 |title=A Phenom-enal Rumble |url=http://www.wwe.com/shows/royalrumble/history/2007/matches/35535102/results/ |access-date=January 26, 2023 |publisher=World Wrestling Entertainment}}

Image:Michaels-Cena.jpg on an episode of Raw in 2007]]

On the January 29 episode of Raw, Michaels captured the World Tag Team Championship with WWE Champion John Cena after defeating Rated-RKO.{{cite web|url=http://www.wwe.com/inside/titlehistory/worldtagteam/4065380 |title=John Cena & Shawn Michaels first World Tag Team title reign |access-date=July 12, 2007 |publisher=World Wrestling Entertainment |url-status=dead |archive-url=https://web.archive.org/web/20070716173509/http://www.wwe.com/inside/titlehistory/worldtagteam/4065380 |archive-date=July 16, 2007}} At WrestleMania 23 on April 1, Cena retained the WWE Championship against Michaels after making him submit to the STFU.{{cite web|first=Louie|last=Dee|title=Detroit, Champ City|date=April 1, 2007|url=http://www.wwe.com/shows/wrestlemania/history/wrestlemania23/matches/39161841/results/|publisher=World Wrestling Entertainment|access-date=July 16, 2008}} The next night on Raw, Michaels and Cena competed in two back-to-back ten team battle royals, winning the first and losing the World Tag Team Championship in the second to The Hardys (Matt and Jeff) when Michaels threw Cena over the top rope.{{cite web|url=http://www.wwe.com/shows/raw/archive/04022007/|title=HBK dumps Cena|first=Noah|last=Starr|access-date=April 5, 2007|date=April 2, 2007|publisher=World Wrestling Entertainment}} Michaels faced off with Cena, Edge and Randy Orton in a fatal four-way match on April 29 at Backlash for the WWE Championship, where Cena retained the title after Michaels performed Sweet Chin Music on Cena, causing him to fall on Orton for the pinfall.{{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=July 16, 2008}}

Michaels then entered a feud with Randy Orton when Orton claimed that he could beat Michaels.{{cite web |last=Golden |first=Hunter |date=May 14, 2007 |title=WWE Raw Results – May 14, 2007 |url=http://www.wrestleview.com/results/raw/raw2006/1179200969.shtml |access-date=July 17, 2008 |publisher=WrestleView.com}} The week before their scheduled match on May 20 at Judgment Day, after Michaels won a match against then-World Heavyweight Champion Edge, Orton attacked him by punting Michaels in the head. Orton assaulted Michaels again prior to their match at Judgment Day, interrupting Michaels's interview segment.{{cite web|first=Louie|last=Dee|url=http://www.wwe.com/shows/judgmentday/history/2007/exclusives/hbkconcussions|title=Is it over for HBK?|access-date=May 25, 2007|date=May 21, 2007|publisher=World Wrestling Entertainment}} Michaels collapsed during their match, causing Orton to win by referee stoppage. Orton continued the beating and performed an RKO to a fallen Michaels, who was removed out of the ring in a stretcher. During the feud, Michaels suffered a storyline concussion. This injury was used to keep Michaels out of action, as he required surgery for his knee.{{cite journal|first=John|last=Mihaly|title=The Showstopper Must Go On|journal=WWE Magazine|date=February 2008|pages=18–20}} Michaels made his return on the October 8 episode of Raw, performing Sweet Chin Music to newly crowned WWE Champion Randy Orton during his title ceremony at the end of the show and then celebrating over the knocked-out champion as Vince McMahon watched.{{cite web|first=Bryan|last= Robinson|url=http://www.wwe.com/shows/raw/archive/10082007/articles/hbkreturns|title=HBK shows Orton his 'appreciation'|access-date=October 9, 2007| date=October 8, 2007|publisher=World Wrestling Entertainment}} On October 28 at Cyber Sunday, Michaels was voted by the fans to face Orton for the WWE Championship, though he won via disqualification when Orton hit Michaels with a low blow, which resulted in Orton retaining the championship.{{cite web|url=http://www.wwe.com/shows/cybersunday/history/2007/matches/52676102/results/|title=Sweet Chin Grand Slam|first=Bryan|last=Robinson|date=October 28, 2007|publisher=World Wrestling Entertainment|access-date=July 16, 2008}} Michaels got another opportunity at the WWE Championship, when he was granted his rematch against Orton on November 18 at Survivor Series.{{cite web|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2007/11/18/4666920.html|archive-url=https://archive.today/20120629045655/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2007/11/18/4666920.html|url-status=usurped|archive-date=June 29, 2012|title=Survivor Series ends with an Edge|access-date=January 29, 2008|publisher=Canadian Online Explorer|work=Slam! Sports|date=November 19, 2007|first=Dale|last=Plummer|author2=Tylwalk, Nick }} In their match, Michaels was banned from using Sweet Chin Music upon request by Orton, referring to as Michaels superkicking Orton week after week.{{cite web|first=Bryan|last=Robinson|url=http://www.wwe.com/shows/survivorseries/history/2007/exclusives/hbkhandcuffed|title=The music is silenced|access-date=February 7, 2008|date=November 7, 2007|publisher=World Wrestling Entertainment}} Michaels lost the match, when Orton performed an RKO for the win, which ended their feud.

Image:Shawn Michaels at WrestleMania XXIV.jpg before his match with Ric Flair]]

Michaels defeated and ended Ric Flair's career in a Career Threatening match on March 30, 2008, at WrestleMania XXIV.{{cite web|first=Bryan|last=Robinson|url=http://www.wwe.com/shows/wrestlemania/history/2008/matches/6464438/results/|title=The End|access-date=March 31, 2008|date=March 30, 2008|publisher=World Wrestling Entertainment}} Afterwards, Batista confronted Michaels about his actions at WrestleMania, calling him selfish and egotistical.{{cite web|first= Mitch|last=Passero|url=http://www.wwe.com/shows/smackdown/archive/04042008/|title=Mixed Emotions|access-date=July 16, 2008|date=April 4, 2008|publisher=World Wrestling Entertainment}} On April 27 at Backlash, with Chris Jericho as the guest referee, Michaels defeated Batista.{{cite web|url=http://www.wrestleview.com/news2008/1209351283.shtml|title=Backlash PPV Results – 4/27 – Baltimore, MD ('New WWE Champion')|last=Martin|first=Adam|date=April 27, 2008|publisher=WrestleView.com|access-date=August 6, 2008}} Jericho then confronted Michaels, in which he admitted to faking a knee injury in order to defeat Batista.{{cite web|first=Andrew|last=Rote|url=http://www.wwe.com/shows/raw/archive/05122008/|title=No time wasted|access-date=July 16, 2008|date=May 12, 2008|publisher=World Wrestling Entertainment}} Michaels defeated Jericho on May 18 at Judgment Day.{{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|publisher=Canadian Online Explorer|work=Slam! Sports}} At One Night Stand on June 1, Michaels lost to Batista in a stretcher match.{{cite web|url=http://www.wwe.com/shows/onenightstand/matches/7117260/results/|access-date=July 16, 2008|title=Promise kept|publisher=World Wrestling Entertainment|date=June 1, 2008}} On the June 9 episode of Raw, Michaels was attacked by Chris Jericho during his talk show segment, The Highlight Reel, being thrown directly through a television screen.{{cite web|first=Aubrey|last=Sitterson|url=http://www.wwe.com/shows/raw/archive/06092008/|title=Cash and Burn|access-date=July 16, 2008|date=June 9, 2008|publisher=World Wrestling Entertainment}} The following week, it was revealed that, within the context of the storyline, Michaels had suffered a detached retina.{{cite web|url=http://www.wwe.com/shows/raw/archive/08042008/articles/michaelsinjuryupdate|title=Truth revealed: Michaels' double injury|access-date=August 12, 2008|date=August 4, 2008|publisher=World Wrestling Entertainment}} On July 20 at The Great American Bash, Jericho defeated Michaels by referee stoppage after assaulting Michaels's eyes.

At SummerSlam on August 17, Michaels announced his retirement from professional wrestling. That night, Jericho punched Michaels's wife in the face.{{cite web|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/08/17/6484406.html|archive-url=https://archive.today/20120730124909/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/08/17/6484406.html|url-status=usurped|archive-date=July 30, 2012|title=SummerSlam comes close to 'blockbuster' status|last=Plummer|first=Dale|author2=Nick Tylwalk |date=August 17, 2008|work=Slam! Sports|publisher=Canadian Online Explorer|access-date=July 28, 2009}} On the August 25 episode of Raw, Michaels renounced his retirement and challenged Jericho to an unsanctioned match at Unforgiven on September 7, which Jericho accepted.{{cite web|url=http://www.wwe.com/shows/raw/archive/08252008/|title=Championship Scramble scrambled|last=Sitterson|first=Aubrey|date=August 25, 2008|publisher=World Wrestling Entertainment|access-date=September 11, 2008}} The next week, they had a contract signing for the match and were involved in a brawl, causing a legit small triceps tear for Michaels.{{cite web|url=http://www.wwe.com/shows/raw/archive/09012008/articles/shawnmichaelsinjurestricep|title=Triceps injury won't stop HBK from going to Unforgiven|date=September 2, 2008|publisher=World Wrestling Entertainment|access-date=September 15, 2008}}{{cite news|url=http://weblogs.baltimoresun.com/sports/wrestling/blog/2008/09/|title=Unforgiven thoughts|last=Eck|first=Kevin|date=September 8, 2008|work=The Baltimore Sun|access-date=September 15, 2008}} He was medically cleared to compete at Unforgiven, and beat Jericho so severely that the referee called the match, making Michaels the winner.{{cite web|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/09/08/6698911.html|archive-url=https://archive.today/20120629151951/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/09/08/6698911.html|url-status=usurped|archive-date=June 29, 2012|title=Scramble matches make for wild Unforgiven|last=Bishop|first=Matt|date=September 8, 2008|work=Slam! Sports|publisher=Canadian Online Explorer|access-date=September 15, 2008}} Later that night, Jericho replaced CM Punk in the World Heavyweight Championship scramble match, and won the title. On October 5 at No Mercy, Michaels was defeated by Jericho in a ladder match for the World Heavyweight Championship.{{cite web |last=Golden |first=Hunter |date=September 15, 2008 |title=Raw Results – 9/15/08 – Memphis, TN (Jericho vs. Punk & 'No Mercy') |url=http://www.wrestleview.com/results/raw/raw2008/1221538363.shtml |access-date=March 24, 2009 |publisher=WrestleView.com}}

File:HBK & jbl.jpg in early 2009.]]In December 2008, having lost his family's savings due to the global recession, Michaels grudgingly accepted a one-year general employment contract from John "Bradshaw" Layfield (JBL).{{cite web|url=http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/12/14/7749336.html|archive-url=https://archive.today/20120629143628/http://slam.canoe.ca/Slam/Wrestling/PPVReports/2008/12/14/7749336.html|url-status=usurped|archive-date=June 29, 2012|title=Armageddon: Hardy finally breaks through|last=Bishop|first=Matt|date=December 14, 2008|work=Slam! Sports|publisher=Canadian Online Explorer|access-date= March 12, 2009}} After failing to help JBL win the World Heavyweight Championship from John Cena on January 25, 2009, at the Royal Rumble,{{cite web|url=http://www.wwe.com/shows/royalrumble/history/2009/matches/9029646/results/|title=Beating the odds|date=January 25, 2009|last=Sitterson|first=Aubrey|publisher=World Wrestling Entertainment|access-date=March 12, 2009}} and being derided for it, Michaels agreed to face JBL in "All or Nothing" match at No Way Out on February 15,{{cite news|url=http://www.wwe.com/shows/raw/archive/02022009/|title=Missouri loves company|last=Adkins|first=Greg|date=February 2, 2009|publisher=World Wrestling Entertainment|access-date=March 12, 2009}} which Michaels won thus letting him out of his contract early while still receiving full payment.{{cite web|url=http://www.wwe.com/shows/nowayout/matches/8281270/results/|title=Sweet Chin Music to our ears|last=Vermillion|first=James|publisher=World Wrestling Entertainment|access-date=March 12, 2009}}

On the March 2 episode of Raw, Michaels became the first person to defeat Vladimir Kozlov, and so earned a match with The Undertaker at WrestleMania 25 on April 5,{{cite web|url=http://www.wwe.com/shows/raw/archive/03022009/|title=Breaking the news|last=Sitterson|first=Aubrey|date=March 2, 2009|publisher=World Wrestling Entertainment|access-date=March 3, 2009}} which he lost thus extending The Undertaker's WrestleMania winning streak to 17–0.{{cite news |last=Matthews |first=Graham |date=March 25, 2011 |title=WrestleMania 25: The Most Disappointing WrestleMania of All Time |work=Bleacher Report |location= |url=https://bleacherreport.com/articles/645529-wrestlemania-25-the-most-disappointing-wrestlemania-of-all-time |access-date=February 19, 2022}}{{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=World Wrestling Entertainment}} Their match was highly acclaimed by critics and audiences alike and is now considered by many to be one of the greatest WrestleMania matches of all time.{{cite news |last=Dilbert |first=Ryan |date=March 8, 2013 |title=WrestleMania Classics: What Made Shawn Michaels vs. Undertaker so Great |work=Bleacher Report |location= |url=https://bleacherreport.com/articles/1558102-wrestlemania-classics-what-made-shawn-michaels-vs-undertaker-so-great |access-date=February 25, 2022}} After WrestleMania, Michaels took a four-month hiatus from WWE.{{cite web|url=https://www.wrestlinginc.com/news/2009/12/shawn-michaels-im-taking-time-off-after-wrestlemania-523917/|title=Shawn Michaels: I'm Taking Time Off After WrestleMania|work=Wrestling Inc.|date=10 December 2009|last=Clark|first=Ryan|access-date=20 January 2024}}

File:Bret vs HBK Jan 4 2010.jpg in January 2010.]]

Michaels returned to WWE programming in a series of segments that aired on the August 10, 2009, episode of Raw, where he had, in storyline, left the WWE. Triple H met with Michaels at an office cafeteria in Texas where he was working as a chef; throughout the segments, Triple H tried to convince Michaels to return to WWE and reform DX. After several incidents during the segments, Michaels agreed to team with Triple H to face The Legacy (Cody Rhodes and Ted DiBiase) at SummerSlam on August 23,{{cite web|url=http://www.wwe.com/shows/raw/results/ |title=North of disorder |date=August 10, 2009 |first=Greg |last=Adkins |access-date=August 10, 2009 |publisher=World Wrestling Entertainment |url-status=dead |archive-url=https://web.archive.org/web/20080514184356/http://www.wwe.com/shows/raw/results/ |archive-date=May 14, 2008}} where DX defeated Legacy.{{cite web|url=http://www.wwe.com/shows/summerslam/history/2009/matches/11196552/results/|title=Results: How DX won the war|last=Sitterson|first=Aubrey|date=August 23, 2009|access-date=August 24, 2009|publisher=World Wrestling Entertainment}} At TLC: Tables, Ladders and Chairs on December 13, DX defeated Jeri-Show (Chris Jericho and Big Show) to win the Unified WWE Tag Team Championship in a Tables, Ladders, and Chairs match (TLC).{{cite web|url= http://pwtorch.com/artman2/publish/PPV_Reports_5/article_37357.shtml|title=Caldwell's WWE TLC PPV Report 12/13: Complete PPV report on Cena vs. Sheamus, DX vs. JeriShow, Taker vs. Batista|last=Caldwell|first=James|date=December 13, 2009|publisher=Pro Wrestling Torch|access-date=December 14, 2009}} On the January 4, 2010, episode of Raw, Michaels buried the hatchet with long-time rival Bret Hart, as they shook hands and hugged in the ring. In contrast to the storylines featured on the show, this was in fact a legitimate reconciliation which laid to rest animosities surrounding the Montreal Screwjob. While some cast doubts on its sincerity, both men have confirmed that it was indeed genuine.{{cite web |url=https://calgaryherald.com/sports/Back+Ring/2425695/story.html |title=Back in the Ring: Hart seeks closure in comeback |work=Calgary Sun |first=Heath |last=McCoy |access-date=January 11, 2010 |date=January 10, 2010 |archive-url=https://web.archive.org/web/20100308020451/http://www.calgaryherald.com/sports/Back+Ring/2425695/story.html |archive-date=March 8, 2010 |url-status=dead}}{{cite web|url=http://weblogs.baltimoresun.com/sports/wrestling/blog/2010/03/qa_with_shawn_michaels_1.html|title=Q&A with Shawn Michaels|work=The Baltimore Sun|first=Kevin|last=Eck|date=May 16, 2007|access-date=April 4, 2010|archive-date=March 30, 2010|archive-url=https://web.archive.org/web/20100330074622/http://weblogs.baltimoresun.com/sports/wrestling/blog/2010/03/qa_with_shawn_michaels_1.html|url-status=dead}} DX lost the Unified WWE Tag Team Championship in a triple threat match to the team of The Miz and Big Show on the February 8 episode of Raw; the match also included The Straight Edge Society (CM Punk and Luke Gallows).{{cite web|first= Greg|last=Adkins|url=http://www.wwe.com/shows/raw/archive/02082010/|title=Raw's pit stomp|access-date=February 9, 2010|date=February 8, 2010| publisher=World Wrestling Entertainment}} On February 21 at Elimination Chamber, Michaels cost The Undertaker the World Heavyweight Championship in the main event.{{cite web| first=Greg|last=Adkins|url=http://www.wwe.com/shows/eliminationchamber/matches/13422574/results/|title=Heartbroken|access-date= February 21, 2010|date=February 21, 2010|publisher=World Wrestling Entertainment}} At WrestleMania XXVI on March 28, Michaels lost to The Undertaker and, as a result, he was forced to retire due to the match stipulation, the same way Michaels ended Ric Flair's career.{{cite web|first=Dale|last=Plummer|author2=Nick Tylwalk|url=http://slam.canoe.ca/Slam/Wrestling/WrestleMania26/2010/03/29/13391706.html|archive-url=https://archive.today/20120630024236/http://slam.canoe.ca/Slam/Wrestling/WrestleMania26/2010/03/29/13391706.html|url-status=usurped|archive-date=June 30, 2012|title=Undertaker ends Shawn Michaels' career in thrilling rematch to cap off Wrestlemania XXVI|access-date=October 29, 2010|date=March 29, 2010|publisher=Canadian Online Explorer|work=Slam! Sports}} The following night, on the March 29 episode of Raw, Michaels gave an emotional farewell speech, departing with the familiar sentence, "Shawn Michaels has left the building."{{cite web|url=http://slam.canoe.ca/Slam/Wrestling/2010/03/29/13402836.html|archive-url=https://archive.today/20120716233427/http://slam.canoe.ca/Slam/Wrestling/2010/03/29/13402836.html|url-status=usurped|archive-date=July 16, 2012|title=Raw: HBK says farewell to the WWE Universe|date=March 29, 2010|last=Plummer|first=Dale|access-date=March 30, 2010|work=Slam! Sports|publisher=Canadian Online Explorer}}

In an interview with Bill Simmons of ESPN.com shortly after his retirement, Michaels stated that his decision to retire came a month before WrestleMania 25, when a backstage employee asked about his son Cameron, and, in response to Shawn telling the employee that he'd just turned nine, the employee said that he was "halfway gone"; meaning that he was halfway to his eighteenth birthday, and after that, he'd be "gone". The statement affected Michaels deeply; he did not want to be absent when his son left home, so he decided that year would be his last year as an active wrestler.{{cite web |last=Simmons |first=Bill |date=August 13, 2010 |title=WWE News: Shawn Michaels explains why he retired and why he will not return for another match, comments on his relationship with Vince McMahon |url=http://www.prowrestling.net/artman/publish/WWE/article10013529.shtml |access-date=January 26, 2023 |website=Pro Wrestling Dot Net}}

On the December 13 episode of Raw, Michaels won the Slammy Award for Moment of the Year for his match against The Undertaker at WrestleMania XXVI and accepted it via satellite.{{cite web |title=2010 Slammy Awards |url=http://www.wwe.com/shows/raw/slammyawards10/ |access-date=December 14, 2010 |publisher=World Wrestling Entertainment}} Three days later, he announced a long-term deal with WWE, where he would serve in an ambassadorial role.{{cite news|first=Anthony|last=Castellano|url=http://www.newsday.com/sports/the-steel-cage-1.811995/shawn-michaels-announces-long-term-deal-with-wwe-1.2551687|title=Shawn Michaels announces "long-term" deal with WWE|access-date=December 22, 2010|date=December 18, 2010|work=Newsday}} Michaels made his in-person television return at the December 11 Tribute to the Troops taping, where he and Triple H had a one-night only DX reunion.{{cite web |last=Gerweck |first=Steve |date=December 12, 2010 |title=Spoilers: WWE 2010 Tribute to the Troops results |url=http://www.wrestleview.com/viewnews.php?id=1292171243 |access-date=December 21, 2010 |publisher=WrestleView.com}}File:Hall of fame 2011.jpg, with other 2011 WWE Hall of Fame inductees]]Michaels appeared on the January 10, 2011, episode of Raw, where he was announced as a WWE Hall of Fame class of 2011 inductee. After being ridiculed by Alberto Del Rio later that night, Michaels hit Del Rio with Sweet Chin Music.{{cite web|first=Greg|last=Adkins|url=http://www.wwe.com/shows/raw/results/16786978/|title=Tennessee titan|access-date=January 11, 2011|date=January 10, 2011|publisher=World Wrestling Entertainment}} On the March 28 episode of Raw, Michaels addressed Triple H and The Undertaker about their match at WrestleMania XXVII.{{cite web|first=Dale|last=Plummer|url=http://slam.canoe.ca/Slam/Wrestling/2011/03/28/17788296.html|archive-url=https://archive.today/20120715004938/http://slam.canoe.ca/Slam/Wrestling/2011/03/28/17788296.html|url-status=usurped|archive-date=July 15, 2012|title=Raw: One last push toward Wrestlemania|access-date=March 30, 2011|date=March 28, 2011|publisher=Canadian Online Explorer|work=Slam! Sports}} Michaels was inducted into the WWE Hall of Fame on April 2 by Triple H. They were also joined by fellow Kliq members Kevin Nash (who had returned to WWE for the Royal Rumble) and Sean Waltman.{{cite news|first=Kevin|last=Eck|url=http://weblogs.baltimoresun.com/sports/wrestling/blog/201/04/thoughts_on_wwe_hall_of_fame_ceremony_1.html|title=Thoughts on WWE Hall of Fame ceremony|access-date=October 30, 2011|date=April 3, 2011|work=The Baltimore Sun}} He returned on the June 27 episode of Raw, where he was confronted by CM Punk, and superkicked David Otunga and Michael McGillicutty. Later that night, when Diamond Dallas Page's special appearance was interrupted by Drew McIntyre, he superkicked McIntyre.{{cite web|first=Dale|last=Plummer|url=http://slam.canoe.ca/Slam/Wrestling/2011/06/27/18343201.html|archive-url=https://archive.today/20120716154004/http://slam.canoe.ca/Slam/Wrestling/2011/06/27/18343201.html|url-status=usurped|archive-date=July 16, 2012|title=Punk overshadows Raw Roulette|access-date=October 30, 2011|date=June 27, 2011|publisher=Canadian Online Explorer|work=Slam! Sports}}

In June 2011, Jim Ross, Michaels and Hart announced that the three were working on a DVD chronicling the careers of Hart and Michaels that the WWE was planning to release in October 2011. The subject of the DVD was their on-screen rivalry and real-life conflicts, with a particular focus on the Montreal Screwjob. In his tweet, Hart described working on the DVD as a "cathartic" experience, and Ross asserted that both Hart and Michaels had been very honest and emotional in their interviews. The DVD, Shawn Michaels vs Bret Hart: WWE's Greatest Rivalries, was released in November 2011.{{cite web |last=Byer |first=Matthew |date=November 6, 2011 |title=Bret vs Shawn DVD doesn't disappoint |url=https://slamwrestling.net/index.php/2011/11/06/bret-vs-shawn-dvd-doesnt-disappoint/ |access-date=January 26, 2023 |website=Slam! Wrestling |publisher=Canadian Online Explorer}}

On the February 13, 2012, episode of Raw SuperShow, Michaels confronted Triple H about accepting The Undertaker's challenge for a Hell in a Cell match on April 1 at WrestleMania XXVIII, and announced he would be the special guest referee for it.{{cite web |title=WWE Raw SuperShow: February 13, 2012 |url=https://www.wwe.com/shows/raw/2012-02-13 |access-date=February 13, 2012 |website= |publisher=WWE}} Michaels appeared on the August 6 episode of Raw where he was confronted by Brock Lesnar,{{cite web |last1=Herrera |first1=Tom |title=Raw results: Big Show KOs his foes; Shawn Michaels backs Triple H at SummerSlam |url=https://www.wwe.com/shows/raw/2012-08-06/wwe-raw-results |access-date=August 6, 2012 |website= |publisher=WWE}} who (kayfabe) broke Michaels's arm after putting it in a Kimura Lock the following week.{{cite web |last1=Herrera |first1=Tom |title=Raw results: Brock Lesnar unleashes a world of pain on Shawn Michaels |url=https://www.wwe.com/shows/raw/2012-08-13/wwe-raw-results |access-date=August 13, 2012 |website= |publisher=WWE}} On the April 1, 2013, episode of Raw, Michaels returned to offer to corner Triple H in his match with Brock Lesnar on April 7 at WrestleMania 29.{{cite web |last1=Benigno |first1=Anthony |title=Raw results: The Rock vows victory, HBK returns, and CM Punk strikes the heart of The Undertaker |url=https://www.wwe.com/shows/raw/2013-04-01/wwe-raw-results |access-date=April 1, 2013 |website= |publisher=WWE}} During that match, Michaels superkicked an interfering Paul Heyman, helping Triple H win and keep his job.{{cite web |last1=Melok |first1=Bobby |date=March 18, 2013 |title=Triple H def. Brock Lesnar (No Holds Barred Match; If Lesnar won, Triple H would have had to retire) |url=https://www.wwe.com/shows/wrestlemania/29/triple-h-brock-lesnar |access-date=April 7, 2013 |website= |publisher=WWE}}

At Hell in a Cell on October 27, Michaels served as the special guest referee for the vacant WWE Championship Hell in a Cell match between Daniel Bryan and Randy Orton, performing Sweet Chin Music on Bryan so Orton could win.{{Cite web |last=Benigno |first=Anthony |date=October 7, 2013 |title=Randy Orton def. Daniel Bryan |url=https://www.wwe.com/shows/hellinacell/2013/daniel-bryan-vs-randy-orton-wwe-championship-hell-in-a-cell-match |access-date=January 26, 2023 |publisher=WWE}} The next night on Raw, Michaels explained he was upset with Bryan for attacking Triple H during the match and degraded him for not showing him respect, turning heel for the first time since 2005. Bryan applied the "Yes!" Lock on Michaels to end the segment.{{Cite web |last=Nemer |first=Paul |date=October 29, 2013 |title=WWE RAW Results – 10/28/13 (WWE Title Celebration) |url=https://www.wrestleview.com/wwe-raw-results/44647-wwe-raw-results-10-28-13-wwe-title-celebration/ |access-date=January 26, 2023 |publisher=WrestleView.com}}

On April 3, 2016, at WrestleMania 32, Michaels, as a face, made an appearance during the event in his in-ring attire, confronting The League of Nations alongside Mick Foley and Stone Cold Steve Austin, where Michaels delivered Sweet Chin Music to Alberto Del Rio and King Barrett before celebrating with Foley, Austin and The New Day.{{Cite web |last=McAvennie |first=Michael |date=April 3, 2016 |title=The League of Nations def. The New Day (Non-Title Match) |url=https://www.wwe.com/shows/wrestlemania/32/new-day-league-nations-results |access-date=January 26, 2023 |publisher=WWE}} In late 2016, Michaels became a trainer at the WWE Performance Center.{{cite web |last=Currier |first=Joseph |date=August 15, 2016 |title=Shawn Michaels teaching class at WWE Performance Center |url=https://www.f4wonline.com/news/wwe/shawn-michaels-teaching-class-wwe-performance-center-218711 |access-date=January 26, 2023 |work=Wrestling Observer Newsletter}} According to Pro Wrestling Torch in 2017, Michaels along with Terry Taylor teach the finishing class at the Performance Center, the last of four levels of classes.{{cite web |last1=Radican |first1=Sean |date=September 6, 2017 |title=Update on newly signed former ROH talent at WWE's Performance Center |url=http://www.pwtorch.com/site/2017/09/06/update-newly-signed-roh-talent-wwes-performance-center-plans-dijak-rush-differ-oreilly-cole-fish/ |access-date=September 7, 2017 |website= |publisher=Pro Wrestling Torch}} He appeared on the January 9, 2017, episode of Raw to promote his new film. He was then confronted by Rusev, Lana and Jinder Mahal, before Enzo Amore and Big Cass came to Michaels's side, leading to a match between Big Cass and Mahal, which Cass won after Michaels superkicked Rusev at ringside, distracting Mahal.{{Cite web |last=Martin |first=Adam |date=January 9, 2017 |title=WWE RAW Results – 1/9/17 (Live from New Orleans, Undertaker and HBK return, Handicap U.S. Title Match) |url=https://www.wrestleview.com/wwe-raw-results/71612-wwe-raw-results-1917-live-new-orleans-undertaker-hbk-return-handicap-u-s-title-match/ |access-date=January 26, 2023 |publisher=WrestleView.com}} On the March 13 episode of Raw, Michaels gave Roman Reigns advice about The Undertaker for their match at WrestleMania 33, before Braun Strowman attacked Reigns on the entrance ramp.{{Cite web |last=Tedesco |first=Mike |date=March 13, 2017 |title=WWE RAW Results – 3/13/17 (Tag Title No. 1 Contenders Match) |url=https://www.wrestleview.com/wwe-raw-results/74332-wwe-raw-results-no-1-contenders-match/ |access-date=January 26, 2023 |publisher=WrestleView.com}} He was one of the many WWE legends who appeared on the January 22, 2018, episode of Raw 25 Years.{{Cite web |title=Raw 25 results, Jan. 22, 2018: Braun Strowman crushes the competition in brutal melee on Raw's epic 25th Anniversary |url=https://www.wwe.com/shows/raw/2018-01-22 |access-date=January 26, 2023 |publisher=WWE}}

At Super Show-Down on October 6, Michaels assisted Triple H in defeating The Undertaker, after which, he was attacked by The Undertaker and Kane.{{Cite web |last=Pappolla |first=Ryan |date=October 6, 2018 |title=Triple H def. The Undertaker |url=https://www.wwe.com/shows/wwe-super-show-down/2018-10-06/the-undertaker-triple-h-results |access-date=January 26, 2023 |publisher=WWE}} On the following episode of Raw, Michaels appeared with Triple H, announcing that he was coming out of retirement for one final match and reforming D-Generation X.{{Cite web |last=Powell |first=Jason |date=October 8, 2018 |title=10/08 Powell's WWE Raw Live TV Review: Shawn Michaels and Triple H respond to being attacked by Undertaker and Kane at WWE Super Show-Down, Trish Stratus appearance, two WWE Super Show-Down rematches |url=https://prowrestling.net/site/2018/10/08/10-08-powells-wwe-raw-live-tv-review-shawn-michaels-and-triple-h-respond-to-being-attacked-by-undertaker-and-kane-at-wwe-super-show-down-trish-stratus-appears-heading-into-her-match-with-alexa-bli/ |access-date=January 26, 2023 |website=Pro Wrestling Dot Net |language=en-US}} On November 2 at Crown Jewel, D-Generation X defeated The Brothers of Destruction.{{Cite web |last=Benigno |first=Anthony |date=November 2, 2018 |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 |access-date=January 26, 2023 |publisher=WWE}} The match was poorly received by fans and critics alike, winning the Wrestling Observer Newsletter's "Worst Match of the Year" award, although PWTorch's Wade Keller considered that "Michaels shows glimpses and didn't embarrass himself".{{Cite web |last=Keller |first=Wade |date=November 2, 2018 |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 |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/ |access-date=January 26, 2023 |publisher=Pro Wrestling Torch}}

File:2014-04-05 10-32-23 NEX-6 DSC08044 (13942380204) (cropped).jpg in 2014]]

In November 2018, Michaels announced he was officially working as a writer and producer on WWE's NXT brand and show, under former D-Generation X cohort Paul Levesque.{{Cite web |last=Windsor |first=William |date=November 26, 2018 |title=Shawn Michaels Reveals That He Helps Write NXT TV, Talks Getting Advice From Triple H For Talent |url=https://www.wrestlinginc.com/news/2018/11/shawn-michaels-reveals-that-he-helps-write-nxt-tv-648218/ |access-date=January 26, 2023 |website=Wrestling Inc.}} In April 2019, Michaels was inducted into the WWE Hall of Fame for a second time, this time as a member of D-Generation X.{{cite web |last=Fiorvanti |first=Tim |date=February 18, 2019 |title=D-Generation X to be inducted into WWE Hall of Fame |url=http://www.espn.com/wwe/story/_/id/26024475 |access-date=February 18, 2019 |publisher=ESPN}} He appeared at Survivor Series on November 22, 2020, during The Undertaker's retirement ceremony.{{Cite web |last=Powell |first=Jason |date=November 22, 2020 |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/ |access-date=January 27, 2023 |website=Pro Wrestling Dot Net}} In September 2021, Levesque stepped away from the brand after experiencing a "cardiac incident". Michaels, in his role as Vice President of Talent Development, took over responsibility for the running of the NXT shows.{{cite magazine |last=Barrasso |first=Justin |date=October 26, 2021 |title=Shawn Michaels Steps Up for Best Friend Triple H After Health Scare |url=https://www.si.com/wrestling/2021/10/26/wwe-nxt-shawn-michaels-triple-h-halloween-havoc |access-date=August 12, 2022 |magazine=Sports Illustrated}} In September 2022, his job title was confirmed as Senior Vice President of Talent Development Creative, responsible for both creative and development at NXT, and for the expansion of NXT UK into NXT Europe in 2023.

On January 23, 2023, at Raw is XXX, Michaels again reunited with D-Generation X (without Billy Gunn, as he was no longer under contract with WWE) until they and Kurt Angle were confronted by Imperium (Gunther, Ludwig Kaiser, and Giovanni Vinci).{{Cite web |last=Powell |first=Jason |date=January 24, 2023 |title=1/23 WWE Raw XXX results: Powell's live review of Austin Theory vs. Bobby Lashley in a No DQ match for the U.S. Title, The Usos vs. Dominik Mysterio and Damian Priest for the Raw Tag Team Titles, Becky Lynch vs. Bayley in a cage match, Sami Zay goes to Tribal Court, legends return, the brand's final push for the Royal Rumble |url=https://prowrestling.net/site/2023/01/23/1-23-wwe-raw-xxx-results-powells-live-review-of-austin-theory-vs-bobby-lashley-in-a-no-dq-match-for-the-u-s-title-the-usos-vs-dominik-mysterio-and-damian-priest-for-the-raw-tag-team-titles-bec/ |access-date=January 27, 2023 |website=Pro Wrestling Dot Net}}

Image:Shawn-Michaels-on-RAW-08.jpg

Widely regarded as one of the greatest professional wrestlers of all time,{{cite magazine |last1=Winkie |first1=Luke |date=July 26, 2016 |title=A definitive ranking of the top 101 wrestlers of all time |url=https://www.si.com/extra-mustard/2016/07/26/wwe-wcw-ecw-100-best-wrestlers-all-time |access-date=November 25, 2020 |magazine=Sports Illustrated |publisher=}} Michaels received praise for several matches, including 15 Match of the Year awards between Pro Wrestling Illustrated and Wrestling Observer Newsletter. Also, his match at WrestleMania 24 against Ric Flair was named Match of the Decade by the Pro Wrestling Illustrated. Dave Meltzer gave him two 5 stars matches (the Ladder match against Razor Ramon at WrestleMania X and the first Hell in a Cell against The Undertaker at Bad Blood 1997). After several acclaimed matches at WrestleMania, Michaels has been known as Mr. WrestleMania.{{Cite web |last=Campbell |first=Brian |date=March 30, 2017 |title=Is Shawn Michaels WWE's real 'Mr. WrestleMania?' Ranking the 15 best |url=https://www.cbssports.com/wwe/news/is-shawn-michaels-wwes-real-mr-wrestlemania-ranking-the-15-best/ |access-date=January 26, 2023 |website=CBS Sports}}{{Cite web |last=Lake |first=Jefferson |date=December 28, 2017 |title=Kevin Owens: Shawn Michaels inspired me to become a wrestler |url=https://www.skysports.com/wwe/news/14203/11187125/kevin-owens-shawn-michaels-inspired-me-to-become-a-wrestler |access-date=January 26, 2023 |website=Sky Sports}} Sumit Rehal of Independent UK in his top 10 WrestleMania matches listed Michaels 3 times (vs Razor Ramon at WrestleMania X, vs Bret Hart at WrestleMania XII and vs The Undertaker at WrestleMania XXV).{{Cite web |last=Rehal |first=Sumit |date=April 5, 2014 |title=WrestleMania 30: Top ten WrestleMania matches of all time |url=https://www.independent.co.uk/sport/general/wwe-mma-wrestling/wrestlemania-30-top-ten-wrestlemania-matches-of-all-time-9241050.html |access-date=January 26, 2023 |website=Independent.co.uk}} In 2016, Dave Richard of CBS Sports ranked his match against Steve Austin at WrestleMania XIV as the best main event in WrestleMania history.{{Cite web |last=Richard |first=Dave |date=April 3, 2016 |title=Ranking every WWE WrestleMania main event match from worst to best |url=https://www.cbssports.com/general/news/ranking-every-wwe-wrestlemania-main-event-match-from-worst-to-best/ |access-date=January 26, 2023 |website=CBS Sports}}

His rivalry with Bret Hart has been named one of the best rivalries in WWE history.{{Cite web |last=Shoemaker |first=David |date=November 7, 2011 |title=Bret Hart vs. Shawn Michaels: Behind One of WWE's Greatest Rivalries |url=https://grantland.com/features/one-wwe-greatest-rivalries/ |access-date=January 26, 2023 |website=Grantland}}

His near hourlong match with John Cena on the April 23, 2007, edition of WWE's longest weekly episodic show Raw is widely regarded as the greatest match in the Raw's history.{{cite web | url=https://tjrwrestling.net/feature/match-review-john-cena-shawn-michaels-raw/ | title=(Almost) 5-Star Match Reviews: John Cena vs. Shawn Michaels - RAW, April 23rd, 2007 – TJR Wrestling | date=January 25, 2023 }}{{cite web | url=https://www.digitalspy.com/tv/ustv/a604970/win-john-cenas-greatest-rivalries-on-blu-ray-signed-by-the-man-himself/ | title=Win a signed John Cena WWE Blu-ray | website=Digital Spy | date=October 21, 2014 }}{{cite magazine | url=https://www.rollingstone.com/culture/culture-lists/top-5-all-time-great-inter-generational-wrestling-showdowns-128721/ | title=Top 5 All-Time Great Inter-Generational Wrestling Showdowns | magazine=Rolling Stone | date=November 7, 2017 }}{{cite web | url=https://superluchas.com/shawn-michaels-recuerda-su-lucha-de-una-hora-con-john-cena-en-wwe-raw/ | title=Shawn Michaels recuerda aquella lucha con John Cena | date=January 24, 2023 }}

Michaels is cited as an inspiration for many wrestlers such as Chris Jericho,{{Cite book|last1=Jericho|first1=Chris|url=http://archive.org/details/lionstalearoundt00jeri|title=A lion's tale : around the world in spandex|last2=Fornatale|first2=Peter T.|date=2007|publisher=New York : Grand Central Pub.|others=Internet Archive|isbn=978-0-446-58006-9}} Kevin Owens, Seth Rollins,{{Cite web |last=Paddock |first=Matty |date=January 11, 2018 |title=Seth Rollins: I want Shawn Michaels match |url=https://www.skysports.com/more-sports/wwe/news/14203/11541746/seth-rollins-i-want-shawn-michaels-match |access-date=December 22, 2021 |website=Sky Sports}} Johnny Gargano,{{cite web | url=https://www.si.com/wrestling/2018/11/16/johnny-gargano-interview-nxt-takeover-wargames-aleister-black | title=Q&A: Johnny Gargano on NXT, the Browns and much more | date=November 16, 2018 }} Adam Cole and numerous other wrestlers.{{Cite web |last=Wilkinson |first=Matthew |date=December 6, 2021 |title=Adam Cole Comments On Relationship With Shawn Michaels Following WWE Departure |url=https://www.wrestlinginc.com/news/2021/12/adam-cole-comments-on-relationship-with-shawn-michaels-following-wwe-departure/ |access-date=January 26, 2023 |website=Wrestling Inc.}}

Hickenbottom's first marriage, to Theresa Wood, soon ended in an amicably settled divorce.{{Harv|Michaels|Feigenbaum|2005|p=194}} He married Rebecca Curci, a former WCW Nitro Girl known as Whisper, at the Graceland Wedding Chapel in Las Vegas on March 31, 1999.{{Harv|Michaels|Feigenbaum|2005|p=296}} Only the couple and an Elvis impersonator were present. They have a son named Cameron Kade (born January 15, 2000) and a daughter named Cheyenne (born August 19, 2004).{{Harv|Michaels|Feigenbaum|2005|p=304}}{{Harv|Michaels|Feigenbaum|2005|p=329}}

In 1996, Hickenbottom posed for a non-nude layout in Playgirl. Only after he posed did he discover Playgirl has a mostly homosexual readership, for which some of his fellow wrestlers teased him.{{Harv|Michaels|Feigenbaum|2005|p=233}}

Hickenbottom is ambidextrous, using his left hand for writing and his right hand for drawing. As a wrestler, he typically kicked with his right leg when performing his finishing move, but used either arm for his signature elbow drop. He had trouble differentiating between right and left, which affected his football games as a child.

In 1987, Hickenbottom developed a pattern of "heavy" substance abuse, which eventually alienated some of his closest friends, and may have explained his reputation for being difficult to work with during the 1990s.{{Cite web |last= |date=May 24, 2012 |title=HBK Talks About Being Difficult To Work With In The 90's |url=https://www.sescoops.com/news/shawn-michaels-talks-about-being-difficult-to-work-with-in-the-90s |access-date=May 30, 2023 |website=SE Scoops |language=en}}{{Cite web |title=Shawn Michaels Reflects On His Behavior In The 90s, Addresses How He'd Handle Such A Troubled Talent |url=https://www.fightful.com/wrestling/shawn-michaels-reflects-his-behavior-90s-addresses-how-he-d-handle-such-troubled-talent |access-date=May 30, 2023 |website=Fightful News |language=en}}{{Cite web |last=Zarka |first=J. P. |date=November 29, 2019 |title=Shawn Michaels and Vader {{!}} How HBK Sabotaged Vader's WWF Career |url=https://prowrestlingstories.com/pro-wrestling-stories/shawn-michaels-vader/ |access-date=May 30, 2023 |website=Pro Wrestling Stories |language=en-US}} He contemplated suicide in the late 1980s, and suggested that psychological intervention was "probably sorely needed" by the late 1990s. His wife Rebecca observed, "There was something in him that he despised, and he was self-destructing." He abandoned his drink-and-drugs lifestyle out of fear that he would negatively influence his young son.

Hickenbottom became a born-again Christian on April 24, 2002.{{cite episode|title=Shawn Michaels|series=Off the Record with Michael Landsberg|series-link=Off the Record with Michael Landsberg|network=TSN|date=March 24, 2003}} He was raised a Catholic, but became a non-denominational Christian because of his wife. His later ring attire often incorporated cross symbols and he made a praying gesture on his knees during ring entrances. He was in the audience for a televised service of John Hagee's Cornerstone Church in his hometown of San Antonio, where he is also a Bible teacher. In 2008, he appeared on a Trinity Broadcasting Network program with fellow wrestler Sting.{{cite web|url=http://www.tbn.org/about/newsletter/index.php/793.html|title=TBN Newsletter|access-date=July 17, 2008|publisher=Trinity Broadcasting Network|archive-date=November 21, 2008|archive-url=https://web.archive.org/web/20081121234502/http://www.tbn.org/about/newsletter/index.php/793.html|url-status=dead}}

Hickenbottom is also a long time fan of the San Antonio Spurs, he's attended home games since the late 1970's and had season tickets for the 1998-1999 lockout shortened National Basketball Association season as the Spurs won their first NBA Championship in franchise history during that time.

Michaels was the host of the outdoor television show, Shawn Michaels' MacMillan River Adventures, in which he and his longtime friend, Keith Mark, owner and operator of the original MacMillan River Adventures camp in Yukon, Canada, hunted big-game animals around the world. This series aired on CarbonTV.{{Cite web|title = Watch the best outdoor shows for free on CarbonTV|url = http://www.carbontv.com/shows/shawn-michaels-mra/|website = CarbonTV|access-date = February 8, 2016}}

During their 2015–16 season, the Pittsburgh Penguins of the National Hockey League named a line, consisting of Carl Hagelin, Nick Bonino and Phil Kessel, the "HBK Line" due to the fact that the trio's first initials, of their last names, recall Michaels's "Heartbreak Kid" moniker.{{cite news |last=Bombulie |first=Jonathan |date=May 18, 2016 |title='HBK' line shines as Penguins take series lead against Lightning |newspaper=Pittsburgh Tribune-Review |url=http://triblive.com/sports/penguins/10481193-74/game-penguins-hagelin |access-date=January 26, 2023}} Pens' game-day staff would regularly play Michaels's theme "Sexy Boy" over the Consol Energy Center PA system after goals or excellent shifts by line members.

After weeks of having fun with Penguins fans on Twitter, the team officially invited Michaels for their Eastern Conference Finals Game 5 matchup with the Tampa Bay Lightning (whose fanbase contains a sizable number of pro wrestlers, including Hulk Hogan and Titus O'Neil, due to Tampa long being a home base for many wrestlers), upon which Michaels accepted. Michaels met with Penguins' owner Mario Lemieux and sat with former Pittsburgh Steelers's defensive lineman Brett Keisel during the game. Keisel also gave Michaels a tour of the city including at the Steelers headquarters and having lunch at Primanti Brothers in the city's Strip District.{{cite magazine|url=https://www.si.com/nhl/2016/05/22/shawn-michaels-pittsburgh-penguins-hbk-line-mario-lemieux-primanti-bros|title=Wrestler Shawn Michaels takes in Game 5 of Penguins-Lightning|magazine=Sports Illustrated|last=Marraza|first=Dan|date=May 22, 2016|access-date=May 31, 2016}} The Penguins lost the game in overtime 4–3 but went on to defeat the Lightning in the series and advance to the Stanley Cup Finals, eventually defeating the San Jose Sharks for the Stanley Cup.

Outside of his numerous appearances with WWE, it was not Michaels first visit to Pittsburgh. In 2013, he appeared at the opening of the first Field & Stream store in suburban Cranberry Township.{{cite web |date=June 11, 2014 |title=WWE Hall of Famer Shawn Michaels 'like kid in a candy store' at new Field & Stream |url=http://www.wtae.com/news/local/butler/wwe-hall-of-famer-shawn-michaels-like-kid-in-a-candy-store-at-new-field-stream/-/10928542/21510198/-/29viiwz/-/index.html |url-status=dead |archive-url=https://web.archive.org/web/20131010070840/http://www.wtae.com/news/local/butler/wwe-hall-of-famer-shawn-michaels-like-kid-in-a-candy-store-at-new-field-stream/-/10928542/21510198/-/29viiwz/-/index.html |archive-date=October 10, 2013 |work=WTAE}}

While the Penguins successfully defended their Stanley Cup championship the following year, the HBK Line was broken up when Kessel was moved to the 2nd line with Evgeni Malkin and Bonino left the team in free agency.

On February 10, 2015, Hickenbottom published an autobiography entitled Wrestling for My Life: The Legend, the Reality, and the Faith of a WWE Superstar. It was co-written by David Thomas.{{cite news |last=Schwartz |first=Nick |date=February 10, 2015 |title=Shawn Michaels opens up on life after wrestling in revealing new book |newspaper=USA Today |url=http://ftw.usatoday.com/2015/02/wwe-shawn-michaels-book-wrestling-for-my-life |access-date=January 26, 2023}}

• The Unauthorized History of DX. Triple H; Shawn Michaels; Aaron Williams (2009). WWE Books.

File:WWE - Wembley Arena 140994 (12).jpg during his reign with Diesel]]

• American Wrestling Association
• AWA World Tag Team Championship (2 times) – with Marty Jannetty
• The Baltimore Sun
• Feud of the Year (2008) {{small|vs. Chris Jericho}}{{cite web|last=Eck|first=Kevin|title=2008 Awards|url=https://www.baltimoresun.com/bs-mtblog-2009-01-2008_awards_1-story.html|work=The Baltimore Sun|date=January 2, 2009|access-date=September 25, 2020|archive-date=February 4, 2021|archive-url=https://web.archive.org/web/20210204084430/https://www.baltimoresun.com/bs-mtblog-2009-01-2008_awards_1-story.html|url-status=dead}}
• Match of the Year (2007) {{small|vs. John Cena on Raw}}{{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}}
• Match of the Year (2008) {{small|vs. Ric Flair at WrestleMania XXIV}}
• Match of the Year (2009) {{small|vs. The Undertaker 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. The Undertaker 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}}
• Wrestler of the Year (2008)
• Cauliflower Alley Club
• Art Abrams Lifetime Achievement/Lou Thesz Award (2018){{cite web|last=Lee|first=Joseph|title=Shawn Michaels To Be Honored By Cauliflower Alley Club This April|url=https://411mania.com/wrestling/shawn-michaels-honored-cauliflower-alley-club-april/|work=411Mania|date=February 10, 2018|access-date=September 27, 2020}}
• CBS Sports
• Worst Angle of the Year (2018) {{small|with Triple H vs. The Undertaker and Kane}}{{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}}
• Central States Wrestling
• NWA Central States Tag Team Championship (1 time) – with Marty Jannetty
• Continental Wrestling Association
• AWA Southern Tag Team Championship (2 times) – with Marty Jannetty{{cite book | first1=Royal |last1=Duncan |first2=Gary |last2=Will | title=Wrestling title histories: professional wrestling champions around the world from the 19th century to the present |location=Waterloo, Ontario |orig-year=2000.|chapter= (Memphis, Nashville) Tennessee: Southern Tag Team Title [Roy Welsch & Nick Gulas, Jerry Jarrett from 1977] | pages= 185–189| publisher=Archeus Communications |year=2006 | isbn=0-9698161-5-4}}{{cite web | url=http://www.wrestling-titles.com/us/tn/cwa/awa-s-t.html | title=Southern Tag Team Title | work=Wrestling-Titles | access-date=January 19, 2020}}
• Pro Wrestling Illustrated
• Feud of the Decade (2000–2009) vs. Chris Jericho
• Feud of the Year (2008) vs. Chris Jericho
• Match of the Decade (2000–2009) vs. Ric Flair at WrestleMania XXIV
• Match of the Decade (2010–2019) vs. The Undertaker at WrestleMania XXVI
• Match of the Year (1993) vs. Marty Jannetty on Monday Night Raw on May 17
• Match of the Year (1994){{cite journal|title=PWI Awards|year=1996|journal=1996 Wrestling Almanac & Book of Facts}} vs. Razor Ramon in a ladder match at WrestleMania X
• Match of the Year (1995) vs. Diesel at WrestleMania XI
• Match of the Year (1996) vs. Bret Hart in an Iron Man match at WrestleMania XII
• Match of the Year (2004){{cite web|first=Chris |last=Olds |url=http://blogs.orlandosentinel.com/sports_sportsstuff/2008/03/24-days-of-w-17.html |title=24 days of WrestleMania Memorabilia Countdown: No. 7, Shawn Michaels |access-date=August 6, 2008 |date=March 24, 2008 |work=Orlando Sentinel |archive-url=https://web.archive.org/web/20090501174402/http://blogs.orlandosentinel.com/sports_sportsstuff/2008/03/24-days-of-w-17.html |archive-date=May 1, 2009 |url-status=dead}} vs. Chris Benoit and Triple H at WrestleMania XX
• Match of the Year (2005) vs. Kurt Angle at WrestleMania 21
• Match of the Year (2006) vs. Vince McMahon in a No Holds Barred match at WrestleMania 22
• Match of the Year (2007) vs. John Cena on Raw on April 23
• Match of the Year (2008) vs. Ric Flair at WrestleMania XXIV
• Match of the Year (2009){{cite journal|year=2010|journal=Pro Wrestling Illustrated|volume=31|issue=3|pages=78–79|title=PWI Award: Match of the year}} vs. The Undertaker at WrestleMania 25
• Match of the Year (2010) vs. The Undertaker in a career vs. streak match at WrestleMania XXVI
• Most Inspirational Wrestler of the Decade (2000–2009)
• Most Inspirational Wrestler of the Year (2010){{cite web|url=http://prowrestlingillustrated.blogspot.com/2011/01/achievement-awards-inspirational.html|title=Achievement Awards: Inspirational|date=January 4, 2010|access-date=January 5, 2010|work=Pro Wrestling Illustrated}}
• Most Popular Wrestler of the Year (1995, 1996)
• Ranked No. 1 of the top 500 singles wrestlers in the PWI 500 in 1996{{cite journal|title=PWI Awards|year=2008|journal=2008 Wrestling Almanac & Book of Facts|volume=29|issue=5|page=32|id= 1043-7576}}
• Ranked No. 10 of the top 500 singles wrestlers of the PWI Years in 2003
• Ranked No. 33 and No. 55 of the top 100 tag teams of the PWI Years with Marty Jannetty and Diesel, respectively, in 2003
• Professional Wrestling Hall of Fame
• Class of 2017
• Sports Illustrated
• Ranked No. 8 of the 20 Greatest WWE Wrestlers Of All Time {{cite magazine |last1=Pullar III |first1=Sid |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 |date=September 30, 2024 |access-date=26 November 2024}}
• Texas All-Star Wrestling
• TASW Texas Tag Team Championship (2 times) – with Paul Diamond
• TASW Six-Man Tag Team Championship (1 time) – with Paul Diamond & DJ Peterson{{Cite web|url=http://www.wrestling-titles.com/us/tx/c/taw/tas-6.html|title=TASW Texas 6-man Tag Team Title (Texas)|website=Wrestling-Titles.com}}
• Texas Wrestling Alliance
• TWA Heavyweight Championship (1 time){{cite web |last=Johnson |first=Mike |date=April 4, 2013 |title=4/4 This Day in History |url=https://www.pwinsider.com/article/76554/44-this-day-in-history.html?p=1 |access-date=June 25, 2019 |website= |publisher=Pro Wrestling Insider}}
• World Wrestling Federation / Entertainment / WWE
• WWF Championship (3 times)
• World Heavyweight Championship (1 time)
• WWF Intercontinental Championship (3 times)
• WWF European Championship (1 time)
• WWE Tag Team Championship (1 time){{cite web |title=WWE: Inside WWE > Title History > WWE Tag Team |url=http://www.wwe.com/inside/titlehistory/wwetag/ |access-date=April 4, 2010 |publisher=World Wrestling Entertainment}} – with Triple H
• WWF/World Tag Team Championship (5 times){{cite web |title=WWE: Inside WWE > Title History > World Tag Team |url=http://www.wwe.com/inside/titlehistory/worldtagteam/ |access-date=April 4, 2010 |publisher=World Wrestling Entertainment}} – with Diesel (2), Stone Cold Steve Austin (1), John Cena (1), Triple H (1)
• Royal Rumble (1995, 1996)
• First Grand Slam Champion
• Fourth Triple Crown Champion
• Slammy Award (15 times)
• Best Finisher (1997)
• Best Slammin' Jammin' Entrance (1996)
• Best Tag Team (1994) – with Diesel
• Best Threads (1996)
• Double-Cross of the Year (2013) – For turning on Daniel Bryan and costing him the WWE Championship at Hell in a Cell.
• Leader of the New Generation (1996)
• Master of Mat Mechanics (1996)
• Match of the Year (1994, 1996, 1997, 2008, 2009) – vs. Razor Ramon in a ladder match at WrestleMania X; vs. Razor Ramon in a ladder match at SummerSlam; vs Bret Hart at WrestleMania XII; vs The Undertaker at Badd Blood: In Your House; vs Ric Flair at WrestleMania XXIV; vs The Undertaker at WrestleMania 25
• Moment of the Year (2010) – vs. The Undertaker at WrestleMania XXVI
• Squared Circle Shocker (1996) – Won for collapsing; Owen Hart accepts the award for making Michaels collapse
• Worst Tag Team (1994) – with Diesel
• WWE Hall of Fame (2 times)
• Class of 2011 – individually
• Class of 2019 – as a member of D-Generation X
• Wrestling Observer Newsletter
• Best Babyface (1996){{cite news|last=Meltzer|first=Dave|date=February 1, 2010|title=2009 Wrestling Observer Newsletter Awards|periodical=Wrestling Observer Newsletter|location=Campbell, CA|pages=1–12|issn=1083-9593}}
• Feud of the Year (2004) vs. Chris Benoit and Triple H
• Feud of the Year (2008) vs. Chris Jericho
• Match of the Year (1994) vs. Razor Ramon in a ladder match at WrestleMania X
• Match of the Year (2008) vs. Chris Jericho in a ladder match at No Mercy
• Match of the Year (2009) vs. The Undertaker at WrestleMania 25
• Match of the Year (2010) vs. The Undertaker at WrestleMania XXVI{{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}}
• Worst Match of the Year (2018) with Triple H vs. The Undertaker and Kane at Crown Jewel
• Best Pro Wrestling DVD (2011) Greatest Rivalries: Shawn Michaels vs. Bret Hart
• Most Charismatic (1995, 1996)
• Tag Team of the Year (1989) with Marty Jannetty as The Rockers
• Worst Feud of the Year (2006) with Triple H vs. Shane and Vince McMahon
• Wrestling Observer Newsletter Hall of Fame (Class of 2003){{cite magazine|url=http://www.pwi-online.com/pages/hallofame.html|title=Wrestling Observer Hall of Fame|access-date=February 2, 2010|magazine=Pro Wrestling Illustrated|archive-date=July 14, 2008|archive-url=https://web.archive.org/web/20080714111434/http://pwi-online.com/pages/hallofame.html|url-status=dead}}

{{Reflist|refs=

• {{cite web|url=https://tribune.com.pk/story/1470551/5-wwe-dream-matches-never-happenned/|title=5 WWE dream matches that never happened|last=Aijaz|first=Rahul|date=July 31, 2017|website=The Express Tribune|access-date=August 7, 2017|quote=Michaels, often considered the greatest in-ring talent ever...}}
• {{cite web|url=http://411mania.com/wrestling/from-the-bowery-wwe-top-50-superstars-of-all-time-disc-1/|title=From the Bowery: WWE Top 50 Superstars of All Time (Disc 1)|last=Leighty|first=Robert Jr.|date=February 2, 2011|website=411Mania|access-date=September 22, 2016|quote=This list was voted on by current WWE Super Stars. They asked every Super Star to rate their favorite performers of all time... 1) Shawn Michaels.}}
• {{cite web|url=http://www.pwtorch.com/site/2016/10/19/magic-memories-mania-j-styles-case-best-wrestler-since-shawn-michaels/|title=MAGIC, MEMORIES AND MANIA: A.J. Styles, the case for him being the best wrestler since Shawn Michaels|last=Valentino|first=Shawn|date=October 19, 2016|website=Pro Wrestling Torch|access-date=August 24, 2017|quote=Michaels was the greatest all-around wrestler of all time.}}

}}

• {{Cite book|title=Sex, Lies, and Headlocks: The Real Story of Vince McMahon and World Wrestling Entertainment|first1=Shaun|last1=Assael|first2=Mike|last2=Mooneyham|publisher=Crown|year=2002|isbn=1-4000-5143-6|author1-link=Shaun Assael}}
• {{Cite book|title=Heartbreak & Triumph: The Shawn Michaels Story|first1=Shawn|last1=Michaels|first2=Aaron|last2=Feigenbaum|publisher=WWE Books (Pocket Books)|year=2005|location=New York, New York|isbn=978-0-7434-9380-2|url=https://archive.org/details/isbn_9780743493802}}

• {{Cite news|title=2007 Wrestling Almanac & Book of Facts|work=Wrestling's Historical Cards|publisher=Kappa Publishing|year=2007}}

{{Commons category}}

{{Wikiquote}}

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