Timothy Olyphant

Olyphant was born in Honolulu, Hawaii, but moved to Modesto, California at the age of two.{{cite news|url=http://entertainment.ie/movie/feature/Interview-With-Timothy-Olyphant/202/352.htm|title=Movie – Interview With Timothy Olyphant – entertainment.ie|work=entertainment.ie|access-date=May 9, 2016|archive-url=https://web.archive.org/web/20180630111321/http://entertainment.ie/movie/feature/Interview-With-Timothy-Olyphant/202/352.htm|archive-date=June 30, 2018|url-status=dead}} His parents are Katherine (née Gideon) and John Vernon Bevan Olyphant, who worked as vice president of production at Gallo Winery.{{cite news|url=https://newspaperarchive.com/oakland-tribune/1963-12-30/page-7|work=Oakland Tribune Newspaper |title=Archives|date=December 30, 1963|page= 7 }}{{cite web|url=http://www.tmcnet.com/usubmit/2009/09/06/4356873.htm |title=The Arizona Daily Star, Tucson, Gerald M. Gay column: Remote Controlled : Future FX series has a couple of Tucson ties |website=Tmcnet.com |access-date=May 1, 2012}}{{cite web |url=http://www.arizonafiji.org/fraternity_honored/john-olyphant |title=John Vernon Bevan Olyphant '63; Upsilon Alpha of Phi Gamma Delta |website=Arizonafiji.org |date=April 25, 1941 |access-date=May 1, 2012 |url-status=dead |archive-url=https://web.archive.org/web/20120425155207/http://www.arizonafiji.org/fraternity_honored/john-olyphant |archive-date=April 25, 2012 |df=mdy-all }}{{cite news |last=Zimmerman |first=Paul |title=A Life Less Ordinary |magazine=If |date=April 4, 1999 }} He has an older brother, Andrew, and a younger brother, Matthew.{{cite web|url=http://www.lyncmigration.com/news/2013/01/07/6833977.htm|title=Former Modesto resident hits new peak in acting career|website=lyncmigration|access-date=May 9, 2016}} His parents divorced when he was a teenager; both remarried.California Divorce Index, 1966–1984 : "J V Olyphant vs Katherin G, Stanislaus County, 26 Sep 1983{{cite web|url=https://www.popmatters.com/article/timothy-olyphant-becomes-a-hitman/|title=Timothy Olyphant becomes a 'Hitman'|website=PopMatters|access-date=May 9, 2016}}{{cite news|url=https://books.google.com/books?id=s2IEAAAAMBAJ&q=My%20friends%20were%20everything%20in%20college.%20I%20was%20feeling%20alienated%20with%20my%20parents%20going%20through%20a%20divorce.%20My%20roommates%20and%20I%20smoked%20a%20lot%20of%20weed%20together.%20It%20was%20very%20therapeutic&pg=PA31|title=Hearts Club|work=The Advocate|first=Dennis|last=Hensley|date=June 6, 2000|pages=31–|access-date=May 9, 2016}} He is of English, German, Scottish, Dutch, Irish, and one-eighth Russian-Jewish ancestry.{{Cite web|url=https://www.imdb.com/name/nm0648249/bio/|title=Timothy Olyphant - Biography|website=IMDb}}Stated at 2:01 at https://www.youtube.com/watch?v=J6rlmTWVOi0

Olyphant is a descendant of the Vanderbilt family of New York. His paternal fourth great-grandfather was family patriarch Cornelius Vanderbilt.{{Cite web|url=https://www.britannica.com/biography/Timothy-Olyphant|title=Timothy Olyphant |date=April 17, 2024|website=Britannica}} The surname Olyphant is of Scottish origin. Another paternal fourth great-grandfather, Dr. David Olyphant, was born in Scotland and served as director-general of the Southern hospitals during the American Revolutionary War.[http://fultonhistory.com/Newspapers%25207/New%2520York%2520NY%2520Times/New%2520York%2520NY%2520Times%25201916%2520Jun%252016-30%2520Grayscale/New%2520York%2520NY%2520Times%25201916%2520Jun%252016-30%2520Grayscale%2520%28244%29.pdf New York NY Times 1916 Jun 16–30]{{dead link|date=June 2016}} His third great-grandfather, David Olyphant, and great-great-grandfather, Robert Morrison Olyphant, were both prominent businessmen.{{cite news|url=https://www.nytimes.com/1998/11/07/classified/paid-notice-deaths-emery-adele-hammond-olyphant.html|title=Paid Notice: Deaths EMERY, ADELE HAMMOND OLYPHANT|date=November 7, 1998|work=The New York Times|access-date=May 9, 2016}}{{cite news|url=https://www.nytimes.com/1988/10/23/style/tatyana-doughty-becomes-a-bride.html|title=Tatyana Doughty Becomes a Bride|date=October 23, 1988|work=The New York Times|access-date=May 9, 2016}}{{cite news|url=https://query.nytimes.com/gst/abstract.html?res=9C00E3DD103BEE3ABC4C53DFB3668383609EDE|title=ROBERT M. OLYPHANT DIES AT 93 YEARS – Ex-President of Delaware and amp – Hudson Railroad Was the Oldest Alumnus of Columbia. |date=May 4, 1918|work=The New York Times |access-date=May 9, 2016}}

Olyphant attended Modesto's Fred C. Beyer High School.{{cite news |last=Millegan |first=Lisa |title=Olyphant back with a badge |newspaper=Modesto Bee |date=March 17, 2010 |url=http://www.modbee.com/2010/03/14/1087067/olyphant-back-with-a-badge.html |access-date=June 6, 2010 |archive-url=https://web.archive.org/web/20100501233615/http://www.modbee.com/2010/03/14/1087067/olyphant-back-with-a-badge.html |archive-date=May 1, 2010 |url-status=dead }} Growing up, he was "embarrassed" by the idea of acting, but enjoyed art and drawing.{{cite news|url=https://www.theguardian.com/tv-and-radio/2010/apr/29/timothy-olyphant-justified|title=Timothy Olyphant: A law unto himself|author= Patterson, John|work=The Guardian|access-date=May 9, 2016}}{{cite news|url=http://sharpmagazine.com/2015/04/14/a-man-worth-listening-to-timothy-olyphant/|title=A Man Worth Listening To: Timothy Olyphant|work=Sharp Magazine|access-date=May 9, 2016}} He swam competitively throughout his childhood and was a finalist at the 1986 Nationals, in the 200m Individual Medley.{{cite web|url=https://swimswam.com/celebrity-swim-tuesday-timothy-olyphant/|title=» Celebrity Swim Tuesday: Timothy Olyphant|website=SwimSwam|date=March 13, 2012 |access-date=May 9, 2016}}{{cite web|url=http://www.thetvaddict.com/2012/02/21/timothy-olyphant-justified-interview/|title=Q&A: Timothy Olyphant Tips His Hat to the Cool Cowboy World of JUSTIFIED|author= Vogt, Tiffamy|website=TVaddict|date=February 21, 2012 |access-date=May 9, 2016}} He was then recruited to the University of Southern California by USC Trojans swimming coach Peter Daland.{{cite web|url=http://www.usctrojans.com/sports/m-swim/spec-rel/091911aab.html|title=Former Swimmer Olyphant Emmy Nominee|website=usctrojans|access-date=May 9, 2016|archive-date=May 30, 2016|archive-url=https://web.archive.org/web/20160530101540/http://www.usctrojans.com/sports/m-swim/spec-rel/091911aab.html|url-status=dead}}{{cite news|url=https://www.straight.com/article/olyphant-finds-magic-in-film-collaborations|title=Olyphant finds magic in film collaborations|work=Georgia Straight Vancouver's News & Entertainment Weekly|access-date=May 9, 2016}} When Olyphant first visited the campus as part of a recruitment trip, he hoped to study architecture but was told it would be unmanageable with his training schedule.{{cite news|url=http://www.lamag.com/lastory/timothy-olyphant/|title=Timothy Olyphant|author= St. Pierre Julia |date=April 1, 2012|work=Los Angeles Magazine|access-date=May 9, 2016}}{{cite news|url=https://www.latimes.com/archives/la-xpm-2007-nov-22-gd-fav22olyphant-story.html|title=Timothy Olyphant|work=Los Angeles Times|access-date=May 9, 2016}}

Instead, he opted to earn a Bachelor of Fine Arts. However, Olyphant left university one elective shy of a degree; he returned to finish the degree 30 years later, taking an online course during the COVID-19 pandemic.{{cite web |title=Timothy Olyphant Full Interview |url=https://www.youtube.com/watch?v=lGR0M9vDlcI | archive-url=https://ghostarchive.org/varchive/youtube/20211030/lGR0M9vDlcI| archive-date=2021-10-30|website=CONAN |access-date=May 18, 2021|date=May 17, 2021}}{{cbignore}} In 1990, he planned to finish his degree and apply for a master's degree in fine arts and half-heartedly considered a career in commercial art.{{cite news|url=http://nerdist.com/nerdist-podcast-timothy-olyphant/|title=Nerdist Podcast: Timothy Olyphant|work=Nerdist|access-date=May 9, 2016|archive-url=https://web.archive.org/web/20160129044343/http://nerdist.com/nerdist-podcast-timothy-olyphant/|archive-date=January 29, 2016|url-status=dead|df=mdy-all}} While working as a swimming coach at Irvine Novaquatics,{{cite news|url=https://www.latimes.com/archives/la-xpm-1991-12-25-vw-929-story.html|title=Adults Have the Last Lap : * Masters programs give structured workouts with the guidance of a coach—the same benefits found in schools.|work=Los Angeles Times|access-date=May 9, 2016}}{{cite news|url=https://www.hollywoodreporter.com/news/drama-actor-roundtable-195219|title=The Drama Actor Roundtable|author1=Belloni, Matthew |author2=Hunt Stacey Wilson |date=June 8, 2011|work=The Hollywood Reporter|access-date=May 9, 2016}} Olyphant decided to move to New York to explore other options. He initially performed stand-up comedy: "I'd dabbled [before] and then there was a six-month period where I did it with a certain commitment. Then I'd occasionally go back."{{cite news|url=http://www.mtv.com/news/2560076/mindy-kaling-timothy-olyphant/|archive-url=https://web.archive.org/web/20160214134951/http://www.mtv.com/news/2560076/mindy-kaling-timothy-olyphant/|url-status=dead|archive-date=February 14, 2016|title=Mindy Kaling Gushes Over Timothy Olyphant's 'Mindy Project' Cameo|work=MTV News|access-date=May 9, 2016}}{{cite AV media|url=https://www.youtube.com/watch?v=eZMppksJbBw| archive-url=https://web.archive.org/web/20200418002118/https://www.youtube.com/watch?v=eZMppksJbBw&gl=US&hl=en| archive-date=2020-04-18|title=Timothy Olyphant on O&A (01-25-2007)|date=December 4, 2013|access-date=May 9, 2016|via=YouTube}} Ultimately, he decided to become an actor. In his final year of college, he had taken an acting class as an elective at UC Irvine and found it "really enjoyable".{{cite news|url=http://www.dispatch.com/content/stories/life_and_entertainment/2013/01/21/actor-helps-justified-find-edges-of-humor-violence.html|title=Timothy Olyphant helps 'Justified' find edges of humor, violence|author=Beale, Lewis|work=The Columbus Dispatch|access-date=May 9, 2016}} He completed a two-year acting program at New York's William Esper Studio and began auditioning for roles.{{Cite episode |title=Timothy Olyphant |url=https://www.pbs.org/kcet/tavissmiley/archive/201004/20100412_olyphant.html |series=The Tavis Smiley Show |series-link=The Tavis Smiley Show |credits=Tavis Smiley, host |network=PBS |airdate=April 12, 2010 |access-date=September 16, 2017 |archive-date=June 16, 2010 |archive-url=https://web.archive.org/web/20100616091654/http://www.pbs.org/kcet/tavissmiley/archive/201004/20100412_olyphant.html |url-status=dead }}{{cite web|url=http://www.blogtalkradio.com/robin-milling/2011/06/24/milling-about-flashback-with-timothy-olyphant|title=Milling About Flashback with Timothy Olyphant|date=June 24, 2011|website=BlogTalkRadio|access-date=May 9, 2016}}{{cite news|url=https://www.hollywoodreporter.com/news/25-best-drama-schools-a-797949|title=The 25 Best Drama Schools for a Masters in Fine Arts|author= Appelo, Tim|date=May 29, 2015|work=The Hollywood Reporter|access-date=May 9, 2016}}

Olyphant's first paid acting job was in a 1995 WB television pilot based on 77 Sunset Strip. Phyllis Huffman cast him in the role but he did not have an opportunity to meet the show's producer, Clint Eastwood, who quit days before filming began.{{cite web|url=http://www.wbur.org/npr/134629395/timothy-olyphant-justified-in-laying-down-the-law|title=Timothy Olyphant: 'Justified' In Laying Down The Law|date=March 28, 2011|work=wbur|access-date=May 9, 2016}}{{cite web|url=http://metro.co.uk/2013/05/03/timothy-olyphant-it-means-a-great-deal-that-elmore-leonard-has-watched-justified-3711208/|title=Timothy Olyphant: It means so much that Elmore Leonard likes Justified – Metro News|author=Williams, Andrew|date=May 3, 2013|work=Metro|access-date=May 9, 2016}} Later that year, he made his professional Off Broadway debut in the Playwrights Horizons' production of The Monogamist{{cite web|url=http://www.nydailynews.com/archives/nydn-features/monogamist-stays-faithful-characters-exciting-new-play-poet-wife-rhyme-reason-affairs-article-1.698323|title='Monogamist' Stays Faithful to Its Characters in an Exciting New Play, A Poet & Wife Try to Make Rhyme & Reason of Their Affairs|first=Howard|last=Kissel|date=November 10, 1995|work=New York Daily News|access-date=May 9, 2016}}{{cite web|url=https://apnews.com/2732a2bf592b37477d37fd821f1ac5d7|title='The Monogamist,' A Comedy by Christopher Kyle, Opens Off-Broadway|website=Associated Press |access-date=May 9, 2016}} and received the Theatre World Award for Outstanding Debut Performance.{{cite web |author=Marx, Rebecca Flint |title=Timothy Olyphant > Overview |url=https://www.allmovie.com/artist/timothy-olyphant-232835 |work=Allmovie |access-date=June 7, 2010 }} He starred in the world premiere of The SantaLand Diaries (1996) at the Atlantic Theater Company, a one-man play based on David Sedaris' essay about working as a Macy's department store Christmas elf.{{cite magazine|url=https://www.ew.com/article/1996/12/13/david-sedaris-santaland-diaries|title=David Sedaris' "SantaLand Diaries"|magazine=Entertainment Weekly|access-date=May 9, 2016}} Ben Brantley of The New York Times felt the "charming" Olyphant did "a wonderful job" when imitating other characters but had "a harder time finding a convincing style for the running narrative".{{cite news|url=https://www.nytimes.com/reviews/theater|title=Theater Reviews|newspaper=The New York Times |date=June 2, 2022 }} Howard Kissell of The New York Daily News remarked that he delivered "all the drollery with a perfect deadpan and a twinkle"{{cite news |last=Kissell |first=Howard |title=Santaland |date=November 8, 1996 |url=http://www.nydailynews.com/archives/entertainment/1996/11/08/1996-11-08__santaland___actor_gets_his_.html |newspaper=Daily News |access-date=June 7, 2010 }}{{dead link|date=September 2017 |bot=InternetArchiveBot |fix-attempted=yes }} while David Patrick Stearns of USA Today described him as "an excellent young actor who successfully projects the world-weariness of a young 20-something who slowly evolves into somebody who just might believe in Christmas."{{cite news|last1=Stearns|first1=David Patrick|title=Strange holidays; strained Hellman|work=USA Today|date=November 13, 1996}}

Olyphant made his feature film debut in The First Wives Club (1996) as an eager young director who attempts to cast Elise Elliot (Goldie Hawn) – who thinks she will be playing the leading lady – in the role of the elderly mother.{{cite web|url=http://movieline.com/2000/09/01/timothy-olyphant/|title=Timothy Olyphant|work=Movieline|date=September 2000 |access-date=May 9, 2016}} Airing on the same day of that film's release, he made his television debut in the pilot of the CBS spy series Mr. & Mrs. Smith.{{cite news |last=Shales |first=Tom |title='Mr. and Mrs.': Smith by a Mile |date=September 20, 1996 |url=https://www.washingtonpost.com/wp-srv/style/daily/tv/smith.htm |newspaper=The Washington Post |access-date=June 11, 2010 }}{{cite web|url=http://www.mademan.com/timothy-olyphants-justified-end/|title=Timothy Olyphant's Justified End|work=Made Man|date=January 26, 2015 |access-date=May 9, 2016}} In 1997, Olyphant made a guest appearance as Officer Brett Farraday in three episodes of the ABC police drama High Incident{{cite web|url=https://variety.com/1997/film/news/olyphant-ready-to-scream-1116679247/|title=Olyphant ready to 'Scream'|first=Monica|last=Roman|work=Variety|date=June 23, 1997 |access-date=May 9, 2016}} and returned to New York's Playwrights Horizons to play a supporting role in Plunge.{{cite web|url=http://www.curtainup.com/plunge.html|title=Plunge, a CurtainUp review|author=Elyse Sommer|work=CurtainUp|access-date=May 9, 2016}} He also had minor roles in the romantic comedy A Life Less Ordinary{{cite web|url=https://collider.com/timothy-olyphant-interviewed-catch-and-release/|title=Timothy Olyphant Interviewed – 'Catch and Release'|date=January 17, 2007|work=Collider|access-date=May 9, 2016}} and the CBS television film Ellen Foster.{{cite web|url=https://variety.com/1997/film/reviews/ellen-foster-4-1200452351/|title=Ellen Foster – Variety|first=Tony|last=Scott|work=Variety|date=December 8, 1997 |access-date=May 9, 2016}} Olyphant's most high-profile role of 1997 was as a film student later revealed as one of the killers in the successful horror film Scream 2, bringing "a degree of wild-eyed flair to the role," according to HitFix{{'}}s Chris Eggertsen.{{cite web|url=http://www.hitfix.com/news/the-definitive-ranking-of-every-scream-character|title=The Definitive Ranking of Every Scream Character|work=HitFix|access-date=May 9, 2016}}{{cite web|url=https://variety.com/2015/tv/features/timothy-olyphant-on-scream-2-and-saying-goodbye-to-justified-1201435776/|title=Timothy Olyphant on 'Scream 2' and Saying Goodbye to 'Justified'|first=Debra|last=Birnbaum|work=Variety|date=February 19, 2015 |access-date=May 9, 2016}} He later described the role as "a gift. I had virtually nothing on my resume at that point. I'm sure some of it was made up."

Olyphant returned to television in 1998 for a guest starring role in an episode of the HBO sitcom Sex and the City, playing a love interest for Carrie Bradshaw. Sarah Jessica Parker later said the episode, "Valley of the Twenty Something Guys", was her favorite of the series.{{cite web|url=https://www.huffpost.com/entry/sarah-jessica-parker-sex-and-the-city_n_4470936|title=Sarah Jessica Parker Reveals Favorite 'Sex And The City' Episode|work=HuffPost|date=December 19, 2013 |access-date=February 23, 2020}} Also that year, he had supporting roles in the HBO war film When Trumpets Fade{{cite web|url=https://people.com/archive/picks-and-pans-review-when-trumpets-fade-vol-49-no-24/|title=Picks and Pans Review: When Trumpets Fade|work=People|access-date=February 23, 2020}} and the independent ensemble drama 1999.{{cite press release|url=http://www.prnewswire.com/news-releases/no-aliens-no-armageddon-just-angst-humor-and-the-party-movie-of-the-millennium-1999-is-now-on-sale-77277792.html|title=No Aliens, No Armageddon, Just Angst, Humor and the Party Movie of The Millennium; '1999' Is Now on|date=November 19, 1999|publisher=Vinegar Films|access-date=May 9, 2016}}{{cite magazine|url=https://www.ew.com/article/1999/03/05/1999|title=1999|magazine=Entertainment Weekly|access-date=May 9, 2016}} Two little-seen films were released in 1999: the drama Advice from a Caterpillar, in which Olyphant played the bisexual love interest of Cynthia Nixon's character,{{cite web|url=http://www.playbill.com/news/article/cynthia-nixon-to-take-advice-from-a-caterpillar-in-indie-film-76326|title=Cynthia Nixon to Take Advice From a Caterpillar in Indie Film|work=Playbill|access-date=May 9, 2016}}{{cite magazine|url=https://www.ew.com/article/2007/02/02/advice-caterpillar|title=Advice From a Caterpillar|author=Douglas Carter Beane|magazine=Entertainment Weekly|access-date=May 9, 2016}} and the offbeat ensemble comedy No Vacancy, in which he starred with Christina Ricci.{{cite web|url=https://variety.com/1999/film/reviews/no-vacancy-3-1200457209/|title=No Vacancy – Variety|first=Todd|last=McCarthy|work=Variety|date=April 21, 1999 |access-date=May 9, 2016}} Olyphant received positive notices for portraying a drug dealer in the cult comedy Go (1999).{{cite web|url=https://www.nytimes.com/2012/01/08/arts/television/timothy-olyphant-in-elmore-leonards-justified-on-fx.html|title=Defined by a Smile and a Drawl|date=January 8, 2012|work=The New York Times|access-date=May 9, 2016}} Janet Maslin of The New York Times noted that the role was "played with offbeat flair"{{cite news|url=https://www.nytimes.com/1999/04/09/movies/film-review-pulp-friction-with-drugs-energy-and-attitude.html|title=FILM REVIEW: Pulp Friction, With Drugs, Energy and Attitude |newspaper=The New York Times|date=April 9, 1999 |last1=Maslin |first1=Janet }}{{cite web|url=https://www.huffpost.com/entry/go-15th-anniversary_n_5107394|title=15 Years Later, John August Looks Back On 'Go'|work=HuffPost|date=April 9, 2014 |access-date=May 9, 2016}} while Todd McCarthy of Variety described it as a "deftly etched" performance.{{cite web|url=https://variety.com/1999/film/reviews/go-1200456715/|title=Go|first=Todd|last=McCarthy|work=Variety|date=February 2, 1999 |access-date=May 9, 2016}} He was set to star in the fantasy film Practical Magic, but he was replaced by Aidan Quinn.{{cite web|url=https://variety.com/1998/voices/columns/with-eyes-wound-kidman-gets-practical-1117863197/|title=With 'Eyes' wound, Kidman gets 'Practical'|first=Army|last=Archerd|work=Variety|date=January 21, 1998 |access-date=May 9, 2016}}{{cite magazine|url=https://www.ew.com/article/2013/03/12/timothy-olyphant-jimmy-fallon-practical-magic|title=Timothy Olyphant talks getting fired from 'Practical Magic': VIDEO|magazine=Entertainment Weekly|access-date=May 9, 2016}}

After Olyphant's performance in Go, the film's producer Mickey Liddell offered him his choice of parts in his next project The Broken Hearts Club (2000), a romantic comedy about a group of gay friends living in West Hollywood.{{cite web|url=http://www.sfgate.com/entertainment/article/Heart-to-Heart-With-Timothy-Olyphant-2703149.php|title=Heart to Heart With Timothy Olyphant|author=Edward Guthmann, Chronicle Staff Writer|date=October 1, 2000|work=SFGate|access-date=May 9, 2016}}Hensley, Dennis. (6 June 2000) "[http://www.oocities.org/hollywood/hills/5552/texts/advocate.html Dean Cain and Timothy Olyphant make a splash as gay pals on-screen—and bickering buddies offscreen]." The Advocate Page 44{{cite web|url=https://articles.latimes.com/2000/sep/29/entertainment/ca-28355/2|archive-url=https://web.archive.org/web/20160201201022/http://articles.latimes.com/2000/sep/29/entertainment/ca-28355/2|url-status=dead|archive-date=February 1, 2016|title=Pulling Together on 'Broken Hearts Club'|work=Los Angeles Times|access-date=May 9, 2016}} The Village Voice{{'}}s Dennis Lim commented that his leading performance was better than the film deserved: "Olyphant is charismatic enough for his worst lines not to stick."{{cite web|url=http://www.villagevoice.com/film/boys-in-the-bland-6417547|title=Boys in the Bland|first=Dennis|last=Lim|date=September 26, 2000|work=Village Voice|access-date=May 9, 2016}} However, Mick LaSalle of the San Francisco Chronicle felt he played the part "like a straight actor gaying it up".{{cite web|url=http://www.sfgate.com/movies/article/Broken-Hearts-Gets-Boring-Fast-Gay-friends-go-3237363.php|title='Broken Hearts' Gets Boring Fast / Gay friends go on about romance|author=Mick LaSalle, Chronicle Staff Critic|date=October 6, 2000|work=SFGate|access-date=May 9, 2016}} Olyphant played a detective in the successful action film Gone in 60 Seconds (2000) and joked in an interview about the challenges of playing "second fiddle to a car";{{cite web|url=https://www.latimes.com/archives/la-xpm-2004-apr-08-wk-movies8-story.html|title=Ready to take the lead|work=Los Angeles Times|date=April 8, 2004 |access-date=May 9, 2016}} his performance reminded the Washington Post{{'}}s Stephen Hunter of a young Bill Paxton.{{cite news|url=https://www.washingtonpost.com/wp-srv/entertainment/movies/reviews/gonein60secondshunter.htm|newspaper=The Washington Post|title=Entertainment Guide|access-date=May 9, 2016}}

Olyphant was offered a starring role for a character called Dominic Toretto in another car film called Redline – that would later be retitled The Fast and the Furious. According to Sony producer Neal H. Moritz, "The studio said, 'If you can get Timothy Olyphant to play that role we will greenlight the movie.'" Olyphant declined the role, which went to Vin Diesel. The film went on to be a massive success with nine sequels to date.{{cite magazine|last=Ross|first=Robyn|title=Vin Diesel Almost Wasn't Dom in 'The Fast & the Furious'|url=https://ew.com/movies/2017/04/12/the-fast-the-furious-vin-diesel-dom-timothy-olyphant/|access-date=May 4, 2017|magazine=Entertainment Weekly|date=April 12, 2017}} Olyphant later discussed passing on a lot of roles earlier in his career. In 2011, when asked by The Hollywood Reporter what was the most absurd project he had ever been pitched, he replied, "I've passed on absurd projects and they have become enormous, enormous hits spawning numerous sequels, and I'm not in them."{{cite news|url=https://www.hollywoodreporter.com/news/drama-actor-roundtable-195219|title=The Drama Actor Roundtable|last1=Belloni|first1=Matthew|date=June 8, 2011|work=The Hollywood Reporter|access-date=May 5, 2017|last2=Wilson Hunt|first2=Stacey}} In 2018, he reflected on passing on the role of Toretto in The Fast and the Furious, thinking it would be "stupid" and would bomb at the box office.{{cite news|url=https://www.yahoo.com/entertainment/timothy-olyphant-explains-why-turned-054040971.html|title=Timothy Olyphant explains why he turned down Vin Diesel's role in 'Fast and Furious'|date=March 29, 2018|work=Yahoo! News|access-date=March 23, 2019}}

Olyphant also had supporting roles in the musical comedy Rock Star, the crime drama Auggie Rose,{{cite web|url=https://www.slantmagazine.com/film/review/auggie-rose|title=Auggie Rose|first=Ed|last=Gonzalez|date=November 5, 2001|work=Slant Magazine|access-date=May 9, 2016}}{{cite web|url=https://www.latimes.com/archives/la-xpm-2001-jun-15-ca-10593-story.html|title='Auggie Rose' Tells Involving Tale of Simpler Life|work=Los Angeles Times|date=June 15, 2001 |access-date=May 9, 2016}} and the romantic comedy Head Over Heels (all 2001). He starred in the short film Doppelganger (2001){{cite web|url=http://www.hollywood.com/movies/doppelganger-59307881/|title=Doppelganger – Movie – 2001|work=Hollywood.com|access-date=May 9, 2016}} and appeared in an episode of the Sci-Fi Channel horror series Night Visions (2002).{{cite web|url=http://www.tv.com/shows/night-visions/harmony-74104/|title=Night Visions - Season 1, Episode 22: Harmony - TV.com|publisher=CBS Interactive|work=TV.com|access-date=May 9, 2016}}

The independent drama Coastlines made its debut at the 2002 SXSW Festival, but failed to find a distributor until 2006.{{Cite web |title=Coastlines |work=MovieWeb |date=March 29, 2006 |access-date=March 9, 2019 |url= https://movieweb.com/movie/coastlines/ |quote=Release Date January 15th, 2002 }}{{Cite web |title=IFC Adds Coastlines to {{as written|I|t's [sic]}} First Take Line-Up |author=Jacobs, Evan |work=MovieWeb |date=March 29, 2006 |access-date=March 9, 2019 |url= https://movieweb.com/ifc-adds-coastlines-to-its-first-take-line-up/}} Olyphant starred opposite Josh Brolin as an ex-con who returns to his Florida hometown to collect a $200,000 debt. Kevin Crust of the Los Angeles Times wrote that he "possesses the kind of thousand-yard stare that suggests something deeper going on,"{{cite web|url=https://www.latimes.com/archives/la-xpm-2006-jun-16-et-coast16-story.html|title=Getting bogged down in dreck in Florida|work=Los Angeles Times|date=June 16, 2006 |access-date=May 9, 2016}} while Owen Gleiberman of Entertainment Weekly remarked that "Olyphant, in the sort of role that Paul Newman used to swagger through, has a star's easy command."{{cite magazine|url=https://www.ew.com/article/2006/05/31/coastlines|title=Coastlines|first=Victor|last=Nunez|magazine=Entertainment Weekly|access-date=May 9, 2016}} However, Todd McCarthy of Variety felt his performance "sort of floats along".{{cite web|url=https://variety.com/2002/film/markets-festivals/coastlines-1200551654/|title=Coastlines – Variety|first=Todd|last=McCarthy|work=Variety|date=January 29, 2002 |access-date=May 9, 2016}}

Olyphant's most high-profile role of 2003 was in the Vin Diesel-starring action film A Man Apart. Desson Howe of the Washington Post remarked that Olyphant "gets a kudo or two for [having] the good sense to realize he's playing one of the movie's many one-dimensional characters, so he might as well have insane fun".{{cite news|url=https://www.washingtonpost.com/wp-dyn/content/article/2003/04/04/AR2005033117382.html|title='A Man Apart' Doesn't Stand Out From the Crowd|newspaper=The Washington Post |access-date=May 9, 2016}} Similarly, Mick LaSalle of the San Francisco Chronicle noted that "the most lively character in "A Man Apart" turns out [to be] a middling drug dealer played to the hilt by Timothy Olyphant."{{cite web|url=http://www.sfgate.com/movies/article/Diesel-vehicle-runs-out-of-fuel-Cop-thriller-A-2624373.php|title=Diesel vehicle runs out of fuel / Cop thriller 'A Man Apart' fails to draw out actor's personality|author=Mick LaSalle, Chronicle Movie Critic|date=April 4, 2003|work=SFGate|access-date=May 9, 2016}} He appeared in the film adaptation of Stephen King's horror novel Dreamcatcher as one of four friends attacked by parasitic aliens.{{cite web|url=http://movieweb.com/movie/dreamcatcher/interview-with-jason-lee-timothy-olyphant/|title=Dreamcatcher – Interview with Jason Lee/Timothy Olyphant|access-date=May 9, 2016}}{{cite magazine|url=https://www.ew.com/article/2010/03/16/justified-timothy-olyphant-fx|title=Timothy Olyphant talks 'Justified,' his evolving career, and securing his place on our Dream Emmy Ballot|magazine=Entertainment Weekly|access-date=May 9, 2016}}SPIN May 2003 page 50 An Olyphant Never Forgets by Diana Vadino The film was poorly reviewed, with David Rooney of Variety remarking: "Only Lee and Olyphant come close to hitting the right note of tongue-in-cheek humor that might have made all this palatable. Unfortunately, they're the first to go."{{cite web|url=https://variety.com/2003/film/reviews/dreamcatcher-1200542782/|title=Dreamcatcher – Variety|first=David|last=Rooney|work=Variety|date=March 16, 2003 |access-date=May 9, 2016}} Also in 2003, he appeared in the independent ensemble drama The Safety of Objects.{{cite web|url=https://www.indiewire.com/article/subversive_suburbia_rose_troche_on_the_safety_of_objects|title=Subversive Suburbia; Rose Troche on "The Safety of Object |author=Indiewire|date=March 4, 2003|work=Indiewire|access-date=May 9, 2016}}{{cite web|url=https://www.latimes.com/archives/la-xpm-2003-mar-07-et-kevin7-story.html|title=No 'Safety' from everyday perils|work=Los Angeles Times|date=March 7, 2003 |access-date=May 9, 2016}}

Olyphant received widespread praise for his 2004 performance as a porn film producer in the comedy The Girl Next Door.{{cite web|url=https://www.aintitcool.com/node/16895|title=Mr. Beaks Interviews Luke Greenfield, Director Of THE GIRL NEXT DOOR!!|date=January 28, 2004|work=Aint It Cool News|access-date=May 9, 2016}}{{cite web|url=https://www.huffingtonpost.com/2014/04/15/the-girl-next-door_n_5143633.html|title=The Juice Was Worth The Squeeze: Looking Back On 'The Girl Next Door'|work=The Huffington Post|date=April 15, 2014 |access-date=May 9, 2016}}{{cite web|url=https://www.avclub.com/article/inventory-10-character-actors-who-should-be-in-eve-1547|title=Inventory: 10 Character Actors Who Should Be In Every Movie|website=The A.V. Club |date=May 10, 2006 |access-date=May 9, 2016}} He was initially reluctant to audition for the part, feeling it was too similar to some of his previous roles but, "as my manager dutifully reminded me, not many people saw those movies." Mick LaSalle of the San Francisco Chronicle described the character of Kelly as "a leering, magnetic, frightening, glad-handing, easily-amused, hyper-sensitive, utterly deceitful, maddeningly likable wild man. When Olyphant is on screen, there's the feeling that things might go anywhere."{{cite web|url=http://www.sfgate.com/movies/article/FILM-CLIPS-Also-opening-today-2795760.php#girl|title=FILM CLIPS / Also opening today|date=April 9, 2004|work=SFGate|access-date=May 9, 2016}} A.O. Scott of The New York Times remarked that the part was played with "a throwaway inventiveness"{{cite web|url=https://www.nytimes.com/movie/review?res=9D01EFDC1538F93AA35757C0A9629C8B63|title=Film Review: The Perfect Girl, Except for the Résumé|work=The New York Times|date= April 9, 2004|last=Scott|first=A.O.}} while Kenneth Turan of the Los Angeles Times felt it was played "with wonderful comic zest".{{cite web|url=https://articles.latimes.com/2004/apr/09/entertainment/et-turan9/2|archive-url=https://web.archive.org/web/20160129165617/http://articles.latimes.com/2004/apr/09/entertainment/et-turan9/2|url-status=dead|archive-date=January 29, 2016|title=A 'Girl Next Door' in sheep's clothing|work=Los Angeles Times|access-date=May 9, 2016}} David Edelstein of Slate enjoyed his "spaced-out volatility. Olyphant's Kelly is a brilliant synthesis of poses."{{cite web|url=http://www.slate.com/articles/arts/movies/2004/04/frisky_business.html|title=Stale fantasies in The Girl Next Door.|work=Slate Magazine|date=April 8, 2004 |access-date=May 9, 2016}} Joe Leydon of Variety said he "strikes an impressively deft balance of hearty amiability and understated menace in his scene-stealing turn".{{cite web|url=https://variety.com/2004/film/markets-festivals/the-girl-next-door-3-1200534937/|title=The Girl Next Door – Variety|first=Joe|last=Leydon|work=Variety|date=February 22, 2004 |access-date=May 9, 2016}}

In a 2015 interview, Olyphant reflected on the early stages of his film career, and not getting the leading roles that would have possibly led to major fame: "I got great opportunities right off the bat. And at the same time I either passed or failed to get things that would have made things ridiculously quick. I passed on enormous opportunities only to end up playing the supporting role in the next film. And then I'd think to myself, "What the fuck am I doing? Why did I do that?" But sometimes I feel like I got away with some things, because I've been able to work for a long time and I haven't had to deal with any kind of fame issues."{{cite news|last1=Saltsman|first1=Peter|title=A Man Worth Listening To: Timothy Olyphant|url=http://sharpmagazine.com/2015/04/14/a-man-worth-listening-to-timothy-olyphant/|access-date=May 5, 2017|work=Sharp Magazine|date=April 14, 2015}}

Olyphant came to the attention of a wider audience when he was cast as Sheriff Seth Bullock in HBO's acclaimed western Deadwood, which aired for three seasons from 2004 to 2006. While he had previously been typecast "as a talkative, Jack Nicholson–styled, funny bad boy," in the words of Vulture{{'}}s Matt Zoller Seitz,{{cite web|url=https://www.vulture.com/2015/11/actors-should-be-cast-against-type.html|title=Why More Actors Should Be Cast Against Type|work=Vulture|date=November 4, 2015 |access-date=May 9, 2016}}{{cite web|url=https://www.slantmagazine.com/house/article/deadweek-a-mystery-to-himself-a-portrait-of-seth-bullock|title=Deadweek: A Mystery to Himself—A Portrait of Seth Bullock|author=Matt Zoller Seitz|date=June 11, 2006|work=Slant Magazine|access-date=May 9, 2016}} Deadwood gave him the opportunity to play a righteous, brooding lawman.{{cite web|url=http://www.elsewhere.co.nz/film/2309/deadwood-timothy-olyphant-interviewed-2006-its-always-the-quiet-ones/|title=DEADWOOD; TIMOTHY OLYPHANT INTERVIEWED (2006): It's always the quiet ones . . .|first=Graham|last=Reid|work=Elsewhere by Graham Reid|date=June 10, 2009 |access-date=May 9, 2016}}{{cite web|url=http://www.thestar.com.my/lifestyle/entertainment/tv/news/2007/02/02/honest-lawman/|title=Honest lawman – News – The Star Online|access-date=May 9, 2016}}{{cite web|url=https://www.latimes.com/archives/la-xpm-2007-jun-28-wk-q-a28-story.html|title=A villain, only on the screen|work=Los Angeles Times|date=June 28, 2007 |access-date=May 9, 2016}}{{cite magazine|url=https://www.newyorker.com/magazine/2005/02/14/the-misfit-2|title=The Misfit|first=Mark|last=Singer|date=February 14, 2005|magazine=The New Yorker|access-date=May 9, 2016}} The show's creator, David Milch, said of the casting choice: "Bullock's uprightness is an alternative to going medieval on people. You can see that same fire and that possibility in Tim, even at his most genial ... I'm not sure which poet talked about 'thoughts too deep for words,' but he brings that idea alive ... Tim is a guy that doesn't let himself be known easily."{{cite magazine|last1=Itzkoff|first1=Dave|title=Have Gun, Will Unravel|magazine=Spin|date=March 2005|page=32}}{{cite web|url=https://nymag.com/nymag/culture/tv/64471/|title=A Tall Drink of Still Waters|work=New York Magazine|date=March 3, 2010 |access-date=May 9, 2016}}

While Bullock was initially introduced as Deadwood{{'}}s protagonist, Emily VanDerWerff of The A.V. Club noted that the character of Al Swearengen came to "dominate the show ... This is not to slight Timothy Olyphant. He's a fine actor, and his portrayal of Bullock is frequently very, very good. Bullock is still unquestionably one of the most important characters on the show but the character of a Wild West lawman, no matter how revisionist it was in its portrayal of that lawman as someone who seemed barely in control at all times, just ended up not having as much to do in a blatantly revisionist Western about how chaos gives way to civilization."{{cite web|url=https://www.avclub.com/deadwood-true-colors-full-faith-and-credit-1798206801|title="True Colors"/"Full Faith and Credit"|date=August 19, 2009 |publisher= The A.V. Club|access-date=February 23, 2020}} Matt Feeney of Slate described Bullock as "laconic, feral, hot-tempered and a little vain", and said the character was "not so much played as embodied by Olyphant".{{cite web|url=https://slate.com/culture/2004/05/deadwood-s-linguistic-brilliance.html|title=Talk Pretty|work=Slate Magazine|date=May 21, 2004 |access-date=May 9, 2016}} Alan Sepinwall of HitFix found his performance "fierce and commanding"{{cite web|url=http://www.hitfix.com/blogs/whats-alan-watching/posts/deadwood-rewind-season-1-episode-1-deadwood|title=Deadwood Rewind: Season 1, Episode 1: Deadwood (Veterans edition)|work=HitFix|access-date=May 9, 2016}} while Jeremy Egner of The New York Times said that he showed "a capacity for explosive, nuanced performance barely suggested by earlier roles". The cast were nominated for the 2006 Screen Actors Guild Award for Outstanding Performance by an Ensemble in a Drama Series.

Years later, Olyphant remarked that Deadwood "almost has done more for me since we wrapped than while it was on. I continue to draw from it, to steal from it. I'm much better at my job now because of the things I learned while doing it. David Milch is one of the greatest writers, storytellers, directors, creative forces I've ever been around."{{cite news|url=https://www.theglobeandmail.com/arts/film/timothy-olyphant-is-not-such-a-simple-dude/article4307186/|title=Timothy Olyphant is not such a simple dude|work=The Globe and Mail|date=February 20, 2010 |access-date=May 9, 2016|last1=Schneller |first1=Johanna }} He has been somewhat critical of his own performance: "Frankly, the show is much better than my performance ... Ian was like a little kid, playing with the props and playing with the language and he never lost the sense of fun of it all. I wasn't operating at that same level."{{cite web|url=http://www.cbc.ca/books/2013/03/timothy-olyphant-on-playing-raylan-givens.html|title=Timothy Olyphant on playing Raylan Givens|date=April 15, 2016|access-date=May 9, 2016}}{{cite web|url=http://www.wbur.org/npr/145113773/timothy-olyphant-laying-down-justified-laws|title=Timothy Olyphant: Laying Down 'Justified' Laws|date=January 13, 2012|work=wbur|access-date=May 9, 2016}}

Also in 2006, he made a guest appearance in an episode of the NBC comedy My Name Is Earl.{{cite web|url=http://film.thedigitalfix.com/content/id/63070/my-name-is-earl-season-one.html|title=Film @ The Digital Fix – My Name is Earl: Season One|work=Film @ The Digital Fix|access-date=May 9, 2016}} In 2007, Olyphant starred in the romantic comedy Catch and Release. He knew co-star Jennifer Garner from their days as struggling actors in New York, and was excited for the opportunity to play a romantic lead.{{cite web|url=http://www.thejakartapost.com/news/2012/05/13/timothy-olyphant-justifying-a-character.html|title=Timothy Olyphant: Justifying a character|author=The Jakarta Post|work=The Jakarta Post|access-date=May 9, 2016}} Lael Loewenstein of Variety felt "Olyphant clearly has a bright future"{{cite web|url=https://variety.com/2007/film/markets-festivals/catch-and-release-1200510896/|title=Catch and Release – Variety|first=Lael|last=Loewenstein|work=Variety|date=January 25, 2007|access-date=May 9, 2016}} while Desson Thomson of the Washington Post described him as "the strongest performer here" but that he was "entirely misplaced, an estimable actor caught in a thankless, frilly role".{{cite news|url=https://www.washingtonpost.com/wp-dyn/content/article/2007/01/25/AR2007012501775.html|title='Catch and Release': No Bait on the Hook|newspaper=The Washington Post |access-date=May 9, 2016}} Scott Tobias of The A.V. Club remarked: "Olyphant's trademark volatility makes him a livelier romantic lead than the usual stuffed shirt."{{cite web|url=https://www.avclub.com/review/catch-and-release-3615|title=Catch And Release|website=The A.V. Club |date=January 25, 2007 |access-date=May 9, 2016}} Similarly, Stephanie Zacharek of Salon found him "effective here precisely because he seems a little sharp and dangerous. He's not your typical cuddly romantic lead."{{cite web|url=http://www.salon.com/2007/01/26/catch_2/|title=Catch and Release|first=Stephanie|last=Zacharek|work=Salon|date=January 26, 2007|access-date=May 9, 2016}}

Olyphant's first post-Deadwood roles were the action movies Live Free or Die Hard and Hitman (both 2007). (Coastlines was first screened during the Sundance Film Festival in 2002{{cite web|url=https://variety.com/2006/digital/features/ifc-reels-in-coastlines-1117940499/|title=IFC reels in 'Coastlines'|first=Ian|last=Mohr|work=Variety|date=March 29, 2006|access-date=May 9, 2016}} while Catch and Release was filmed in 2005.{{cite web|url=http://www.people.com/people/archive/article/0,,20147631,00.html|title=Ben & Jen: Oh, Baby!|access-date=May 9, 2016}}) He had bought a house in the weeks before Deadwood{{'}}s cancellation{{cite web|url=http://www.tvinsider.com/article/99/justified-gets-ready-to-take-its-last-shot-in-season-six/|title=Under the Gun: Justified Gets Ready to Take Its Last Shot|work=TV Insider|date=January 27, 2015 |access-date=May 9, 2016}}{{cite web|url=https://www.nytimes.com/2006/06/11/arts/television/11mcki.html|title='Deadwood' Gets a New Lease on Life|date=June 11, 2006|work=The New York Times|access-date=May 9, 2016}} and he later admitted his job choices during this period were for "purely financial reasons". In Live Free or Die Hard, he played a villainous cybersecurity expert.{{cite web|url=http://www.indielondon.co.uk/Film-Review/die-hard-40-timothy-olyphant-interview|title=IndieLondon: Die Hard 4.0 – Timothy Olyphant interview – Your London Reviews|access-date=May 9, 2016}} Both he and Bruce Willis have said his role was underwritten in the script, and he enjoyed working with Willis to develop the character.{{cite web|url=http://www.indielondon.co.uk/Film-Review/die-hard-40-bruce-willis-interview|title=IndieLondon: Die Hard 4.0 – Bruce Willis interview – Your London Reviews|access-date=May 9, 2016}}{{cite web|url=http://www.nydailynews.com/entertainment/tv-movies/good-bad-company-article-1.220502|title=Good to be in bad company|website=New York Daily News |date=June 24, 2007 }}{{cite web|url=http://usatoday30.usatoday.com/life/people/2007-06-28-die-hard-olyphant_N.htm|title='Die Hard' easy for Olyphant |access-date=May 9, 2016}} Peter Travers of Rolling Stone declared him "a master at smiling menace",{{cite magazine|url=https://www.rollingstone.com/movies/reviews/live-free-or-die-hard-20070626|title=Live Free or Die Hard|first=Peter|last=Travers|date=June 26, 2007|magazine=Rolling Stone|access-date=May 9, 2016}} while Mick LaSalle of The San Francisco Chronicle found him "perfectly ice cold".{{cite web|url=http://www.sfgate.com/movies/article/Old-school-bare-knuckle-action-McClane-2572211.php|title=Old-school, bare-knuckle action – McClane delivers and then some|author=Mick LaSalle, Chronicle Movie Critic|date=June 26, 2007|work=SFGate|access-date=May 9, 2016}} However, Manohla Dargis of The New York Times remarked: "Mr. Olyphant has many charms, but annihilating menace is not one of them."{{cite web|url=https://www.nytimes.com/2007/06/27/movies/27hard.html|title=Pick Your Poison: Fists or Fireballs|date=June 27, 2007|work=The New York Times|access-date=May 9, 2016}} He next starred in Hitman, a video game adaptation, as the assassin Agent 47.{{cite web|url=http://www.chud.com/12433/interview-timothy-olyphant-hitman/|title=INTERVIEW: TIMOTHY OLYPHANT (HITMAN)|work=CHUD.com|access-date=May 9, 2016}}{{cite web|url=http://www.basingstokegazette.co.uk/news/1896897.display/|title=Timothy Olyphant – the Hitman with no hair|work=Basingstoke Gazette|date=December 11, 2007 |access-date=May 9, 2016}} He was hired to replace Vin Diesel six weeks before filming began{{cite web|url=http://www.tv.com/news/tvcom-q-and-a-deadwoods-timothy-olyphant-10172/|title=TV.com Q&A: Deadwood's Timothy Olyphant|publisher=CBS Interactive|work=TV.com|access-date=May 9, 2016}}{{cite web|url=http://www.seattletimes.com/entertainment/if-new-die-hard-film-is-a-hit-tim-olyphant-can-live-free/|title=If new|date=June 25, 2007|work=The Seattle Times|access-date=May 9, 2016}} and reluctantly agreed to shave his head.{{cite web|url=https://www.gamesradar.com/exclusive-timothy-olyphant-talks-hitman/|title=Exclusive: Timothy Olyphant talks Hitman|author=Total Film|work=gamesradar|date=March 15, 2007|access-date=May 9, 2016}} The film was commercially successful, grossing over $100 million,{{Cite web|url=https://www.the-numbers.com/movie/Hitman|title=Hitman (2007) - Financial Information|website=The Numbers}} but received negative reviews. Todd McCarthy of Variety described Olyphant as "an actor capable of portraying subtle ambiguities and thought, which suggests he ought to branch out to play something other than baddies".{{cite web|url=https://variety.com/2007/film/markets-festivals/hitman-1200554390/|title=Hitman – Variety|first=Todd|last=McCarthy|work=Variety|date=November 20, 2007|access-date=May 9, 2016}} Nick Schager of Slant Magazine was disappointed to see the actor "reduced to glowering and posing with pistols"{{cite web|url=https://www.slantmagazine.com/film/review/hitman|title=Hitman|first=Nick|last=Schager|date=November 20, 2007|work=Slant Magazine|access-date=May 9, 2016}} while Manohla Dargis of The New York Times felt he was "strangely, at times ridiculously, miscast".{{cite web|url=https://www.nytimes.com/2007/11/21/movies/21hit.html|title=Slaughter on Parade, Without Joystick|date=November 21, 2007|work=The New York Times|access-date=May 9, 2016}} In 2008, he had a supporting role as a lieutenant colonel in the Iraq War drama Stop-Loss,{{cite web|url=https://www.latimes.com/archives/la-xpm-2008-mar-28-et-stop28-story.html|title='Stop' passes muster|work=Los Angeles Times|date=March 28, 2008 |access-date=May 9, 2016}} played a pompous newscaster in the little-seen comedy Meet Bill,{{cite web|url=https://variety.com/2007/film/reviews/bill-1200556342/|title=Bill – Variety|first=Eddie|last=Cockrell|work=Variety|date=September 13, 2007|access-date=May 9, 2016}} voiced the character Cowboy in the video game Turok{{cite web|url=https://www.cinemablend.com/games/Turok-Game-Gets-A-Cast-6636.html|title=Turok Game Gets A Cast|date=October 2, 2007|access-date=May 9, 2016}} and made a guest appearance on the first season of the ABC sitcom Samantha Who? with Christina Applegate.{{cite web|url=https://www.tvguide.com/news/exclusive-deadwood-sheriff-8258/|title=Exclusive: Deadwood Sheriff Books Samantha Who?|first=Michael|last=Ausiello|date=October 22, 2007|work=TV Guide|access-date=May 9, 2016}}{{cite web|url=http://www.thefutoncritic.com/interviews/2009/03/25/interview-samantha-who-co-creator-donald-todd-30802/20090325_samanthawho/|title=Interview: "Samantha Who?" Co-Creator Donald Todd - TheFutonCritic.com|access-date=May 9, 2016}}

Olyphant had a new outlook when choosing his 2009 projects, influenced by his experience with Hitman: "It motivated me to take a little more responsibility with what I was doing ... I was very fond of the director and a lot of the people that worked on the film but there was definitely a part of me that was like, "What am I doing here?'"{{cite web|url=https://www.avclub.com/article/timothy-olyphant-39236|title=Timothy Olyphant|website=The A.V. Club |date=March 17, 2010 |access-date=May 9, 2016}}{{cite news|url=https://www.washingtonpost.com/entertainment/timothy-olyphants-oeuvre-sure-footed-fearless-and-righteous/2011/02/04/ABzArxQ_story.html|title=Timothy Olyphant's oeuvre: Sure-footed, fearless and righteous|first=Jen|last=Chaney|date=February 4, 2011|newspaper=The Washington Post|access-date=May 9, 2016}} He starred as a morphine addict in the little-seen independent heist comedy High Life,{{cite web|url=http://www.tribute.ca/tiff/index.php/2009/09/16/timothy-olyphant-at-tiff-for-high-life/#.Vqzx0PEwgQ4|title=Timothy Olyphant at TIFF for High Life|access-date=May 9, 2016}}{{cite news|url=https://www.thestar.com/entertainment/movies/2010/01/15/timothy_olyphant_weathers_cold_for_his_art.html|title=Timothy Olyphant weathers cold for his art|date=January 15, 2010|work=thestar.com|access-date=May 9, 2016}}{{cite AV media|url=https://www.youtube.com/watch?v=DAtlfkaWAlQ| archive-url=https://ghostarchive.org/varchive/youtube/20211030/DAtlfkaWAlQ| archive-date=2021-10-30|title=Timothy Olyphant on "High Life"|date=December 11, 2009|access-date=May 9, 2016|via=YouTube}}{{cbignore}} with Derek Elley of Variety praising his "terrific" performance.{{cite web|url=https://variety.com/2009/film/markets-festivals/high-life-2-1200473753/|title=High Life – Variety|first=Derek|last=Elley|work=Variety|date=February 9, 2009|access-date=May 9, 2016}}{{cite news|url=https://www.theglobeandmail.com/arts/high-life/article4302013/|title=High Life|work=The Globe and Mail|date=January 14, 2010|access-date=May 9, 2016|last1=Cole|first1=Stephen}} He had a starring role in the thriller A Perfect Getaway as a possible serial killer of fellow holidaymakers in Hawaii. Manohla Dargis of The New York Times enjoyed "the regrettably underemployed" actor's performance,{{cite web|url=https://www.nytimes.com/2009/08/07/movies/07perfect.html|title=Homicidal Maniacs Also Like Hawaii|date=August 7, 2009|work=The New York Times|access-date=May 9, 2016}} Ty Burr of the Boston Globe found him "delightfully confident"{{cite news|url=https://www.boston.com/ae/movies/articles/2009/08/07/getaway_offers_summer_escape/|title=A Perfect Getaway|newspaper=Boston.com|date=August 7, 2009|publisher=The Boston Globe|access-date=May 9, 2016|last1=Burr|first1=Ty}} while Lisa Schwarzbaum of Entertainment Weekly noted he "has a heckuva good time telegraphing macho mania".{{cite magazine|url=https://www.ew.com/article/2009/08/07/perfect-getaway|title=A Perfect Getaway - EW.com|first=David|last=Twohy|magazine=Entertainment Weekly|access-date=May 9, 2016}} He was nominated for the Toronto Film Critics Association Award for Best Supporting Actor.{{cite web|url=https://toronto.citynews.ca/2009/12/16/toronto-film-critics-pick-the-best-of-2009-and-its-a-tie/|title=Toronto Film Critics Pick The Best of 2009 (and it's a tie!)|work=CityNews|date=December 16, 2009 |access-date=May 9, 2016}} He returned to the stage for one night to appear in Standing on Ceremony: The Gay Marriage Plays, benefiting the Human Rights Campaign.{{cite web|url=http://www.playbill.com/news/article/mccormack-olyphant-futterman-and-gant-join-cast-of-standing-on-ceremony-the-163628|title=McCormack, Olyphant, Futterman and Gant Join Cast of Standing on Ceremony: The Gay Marriage Plays|work=Playbill|access-date=May 9, 2016}}{{cite web|url=http://www.afterellen.com/people/59468-la-scene-september-09-mia-kirshners-benefit-glaad-top-chef-invasion-and-the-gay-marriage-plays/3|title=L.A. Scene September '09: Mia Kirshner's Benefit, GLAAD "Top Chef" Invasion, and The Gay Marriage Plays|work=AfterEllen|date=September 24, 2009 |access-date=May 9, 2016}} Also in 2009, he appeared in 11 episodes of the FX legal thriller Damages, as a morally ambiguous love interest for Rose Byrne's character.{{cite web|url=http://www.hollywoodoutbreak.com/2009/08/18/timothy-olyphant-talks-about-deadwood-and-damages/|title=TIMOTHY OLYPHANT TALKS ABOUT DEADWOOD AND DAMAGES – Hollywood Celebrity and Entertainment Daily News|work=Hollywood Outbreak |date=August 18, 2009 |access-date=May 9, 2016 |last1=Outbreak |first1=Hollywood }}{{cite web|url=http://artsbeat.blogs.nytimes.com/2009/04/02/ginia-bellafante-on-the-damages-season-finale-lets-let-bygones-be-bygones/|title=Ginia Bellafante on the 'Damages' Season Finale: Let's Let Bygones Be Bygones|first=Ginia|last=Bellafante|date=April 2, 2009 }} Byrne later said he was her favorite Damages guest star,{{cite web|url=http://news.directv.com/2012/07/18/rose-byrne-talks-damages-season-5-exclusive-interview/|title=Rose Byrne Talks Damages Season 5, Glenn Close & More : DIRECTV News|work=DIRECTV News|access-date=May 9, 2016}}{{cite web|url=https://www.huffingtonpost.com/2012/07/09/rose-byrne-damages-final-season_n_1631834.html|title='Damages' Season 5: Rose Byrne Reflects On Missing Glenn Close And Growing Up With Ellen Parsons|work=The Huffington Post|date=July 9, 2012 |access-date=May 9, 2016}} while FX president John Landgraf sent him the pilot script for another FX project, Lawman (later renamed Justified). In 2010, he starred as the town sheriff in the horror film The Crazies.{{cite web|url=https://www.aintitcool.com/node/44054|title=Capone talks THE CRAZIES and FX's 'Justified' with Timothy Olyphant!!!|author=Capone|date=February 22, 2010|work=Aint It Cool News|access-date=May 9, 2016}} Peter Bradshaw of The Guardian was impressed by the "saturnine screen presence of Timothy Olyphant – that formidable actor who deserves a lead role to match his potential."{{cite web|url=https://www.theguardian.com/film/2010/feb/25/the-crazies-film-review|title=Film review: The Crazies|first=Peter|last=Bradshaw|work=The Guardian|date=February 25, 2010 |access-date=May 9, 2016}} The Hollywood Reporter{{'}}s Michael Rechtshaffen found him "convincing"{{cite web|url=https://www.hollywoodreporter.com/review/crazies-film-review-29354|title=The Crazies – Film Review|author=Michael Rechtshaffen, AP|date=October 14, 2010|work=The Hollywood Reporter|access-date=May 9, 2016}} while Claudia Puig of USA Today enjoyed the "smart, stoic and sympathetic" performance.{{cite web|url=http://usatoday30.usatoday.com/life/movies/reviews/2010-02-26-crazies26_ST_N.htm|title=Familiarly fun 'The Crazies' will get into your head |access-date=May 9, 2016}} He also appeared in the independent comedy Elektra Luxx (2010).{{cite web|url=https://www.timeout.com/us/film/elektra-luxx|title=Elektra Luxx|date=August 3, 2011|work=Time Out New York|access-date=May 9, 2016}}{{cite web|url=http://www.villagevoice.com/film/elektra-luxx-the-hoariest-of-hollywood-whores-6430247|title=Elektra Luxx: The Hoariest of Hollywood Whores|date=March 9, 2011|work=Village Voice|access-date=May 9, 2016 |last1=Holcomb |first1=Mark }}

Olyphant starred in FX's modern-day western series, Justified, as Deputy U.S. Marshal Raylan Givens, who is reassigned to his native Eastern Kentucky following a "Justified," but questionable, quick-draw shooting of a criminal in Miami. There, he encounters many outlaw figures from his childhood, including his father and Boyd Crowder, with whom he dug coal as a teenager.{{cite magazine|url=https://www.rollingstone.com/tv-movies/tv-movie-news/marshal-law-timothy-olyphant-on-ending-justified-52776/|title='Justified'{{'}}s Timothy Olyphant on Ending the Show – Rolling Stone|magazine=Rolling Stone|access-date=September 23, 2024}} Olyphant was initially drawn to "the ease and the charm and the sort of old-fashionedness" of the character but has said he does not consider him a "good guy".{{cite web|url=https://www.huffingtonpost.com/2013/04/02/justified-finale-timothy-olyphant_n_3002055.html|title='Justified' Finale: Timothy Olyphant On Raylan And Boyd's Dynamic, His Relationship With Winona And More|work=The Huffington Post|date=April 2, 2013 |access-date=May 9, 2016}}{{cite web|url=https://www.theguardian.com/tv-and-radio/2013/apr/27/timothy-olyphant-raylan-givens-justified-interview|title=Justified: Timothy Olyphant on Elmore Leonard and the golden age of TV|first=Jonathan|last=Bernstein|work=The Guardian|date=April 27, 2013 |access-date=May 9, 2016}} The character of Raylan Givens was created by novelist Elmore Leonard, appearing in his short story "Fire in the Hole" (2001) and the novels Pronto (1993) and Riding the Rap (1995). Leonard was an executive producer of Justified and befriended Olyphant;{{cite web|url=http://www.starpulse.com/news/Brittany_Frederick/2011/02/10/interview_timothy_olyphant_is_a_justif|title=Interview: Timothy Olyphant Is A 'Justified' Presence|work=Starpulse|access-date=May 9, 2016}}{{cite web|url=http://www.esquire.com/entertainment/interviews/a27364/timothy-olyphant-justified-end-interview/|title=Timothy Olyphant on the End of Justified|first=Dan|last=Reilly|date=February 11, 2014|work=Esquire|access-date=May 9, 2016}}{{cite web|url=https://www.theatlantic.com/entertainment/archive/2012/04/the-strange-glorious-pedigree-of-justified/255674/|title=The Strange, Glorious Pedigree of 'Justified'|first=Allen|last=Barra|work=The Atlantic|date=April 10, 2012 |access-date=May 9, 2016}} his final novel, Raylan (2012), was inspired by the television show.{{cite web|url=https://www.nytimes.com/2012/02/05/books/review/elmore-leonard-returns-with-raylan.html|title=Back on the Case|date=February 5, 2012|work=The New York Times|access-date=May 9, 2016}}

File:Timothy Olyphant Peabody Awards 2011 (8166714309) (cropped).jpg

Raylan Givens has been described by many television critics as the "defining role" of Olyphant's career.{{cite news|url=https://www.washingtonpost.com/wp-dyn/content/article/2011/02/04/AR2011020403248.html|title=Timothy Olyphant's oeuvre: Sure-footed, fearless and righteous|newspaper=The Washington Post |access-date=May 9, 2016}}{{cite magazine|url=https://www.wired.com/2015/04/parting-gifs-justified/|title=Justified Nears Its End, But It Leaves Behind Classic GIFs|date=April 14, 2015|magazine=WIRED|access-date=May 9, 2016}} Brian Lowry of Variety said it was "an unabashed star turn": "There are surely worse ways to be pigeonholed than playing tough, laconic lawmen, and Timothy Olyphant is carving himself a formidable niche in those confines ... It's an enormously appealing performance."{{cite web|url=https://variety.com/2010/tv/reviews/justified-1117942389/|title=Justified – Variety|first=Brian|last=Lowry|work=Variety|date=March 12, 2010 |access-date=May 9, 2016}} Tim Goodman of the San Francisco Chronicle praised "an incredibly riveting performance": "Olyphant's steely gaze, Zen interior and matinee looks called to mind a younger Clint Eastwood."{{cite web|url=http://www.sfgate.com/news/article/Justified-scores-with-hot-star-smart-scripts-3270140.php|title='Justified' scores with hot star, smart scripts|first=Tim|last=Goodman|date=March 15, 2010|work=SFGate|access-date=May 9, 2016}} Daniel Fienberg of HitFix described him as "a tremendously compelling actor. It's not that he thrives only on minimalism, but he gets a lot out of a little. His performance is about potential energy, or potential violence. And Olyphant does "intense and coiled" to perfection."{{cite web|url=http://www.hitfix.com/blogs/the-fien-print/posts/tv-review-fx-s-justified|title=TV Review: FXs Justified|work=HitFix|access-date=May 9, 2016}} Matthew Gilbert of The Boston Globe said: "It's hard to imagine any other actor in the part, as Olyphant milks Raylan's smooth, laconic cowboy style for as much wry humor as he can. He is riveting without a lot of noise — both his body language and his conversation are pared down, and yet his presence is always resonant."{{cite news|url=https://www.boston.com/ae/tv/articles/2011/02/09/in_justified_the_crime_world_grows/|title=In 'Justified,' the crime world grows|work=Boston.com|date=February 9, 2011 |access-date=May 9, 2016|last1=Gilbert |first1=Matthew }} Although Olyphant was nominated for a Primetime Emmy Award for Outstanding Lead Actor in a Drama Series in 2011,{{cite web|url=https://deadline.com/2011/09/emmys-lead-drama-actor-handicap-172726/|title=EMMYS: Lead Drama Actor Handicap|author=The Deadline Team|website=Deadline Hollywood|date=September 18, 2011 |access-date=May 9, 2016}} he and the show were often perceived to have been "snubbed" by Emmy voters.{{cite web|url=http://www.goldderby.com/news/4248/justified-timothy-olyphant-walton-goggins-emmys-tv-entertainment-news.html|title=Hey, where's the Emmy love for critically praised 'Justified'?|author=Gold DerNews Desk|work=Goldderby.com|access-date=May 9, 2016}}{{cite news|url=https://www.vulture.com/2015/07/emmys-2015-who-got-snubbed.html|title=Emmys 2015: Who Got Snubbed?|work=Vulture|access-date=May 9, 2016}}{{cite web|url=https://www.buzzfeed.com/kateaurthur/emmy-snubs-2013-good-wife-americans-tatiana-maslany#.xh2VjXG7m|title=24 Outrageous Emmy Snubs|work=BuzzFeed|date=July 18, 2013 |access-date=May 9, 2016}}{{cite magazine|url=https://www.ew.com/article/2014/07/10/emmy-snubs-2014|title=Emmy nomination snubs: What the Academy got wrong|magazine=Entertainment Weekly|access-date=May 9, 2016}} Matt Zoller Seitz of Vulture suggested this was because it was "the kind of performance that almost nobody recognizes as 'acting.' It's an old-fashioned movie hero performance in which much of the emotional action is internal and articulated with great subtlety."{{cite web|url=https://www.vulture.com/2013/07/seitz-on-the-2013-emmy-nominations-favs-snubs.html|title=Seitz on the 2013 Emmy Nominations: Favs, Snubs – Vulture|work=Vulture|date=July 18, 2013 |access-date=May 9, 2016}} Similarly, Robert Bianco of USA Today commented that his "masterfully complete immersion in the role seems to have masked the talent expended playing it".{{cite web|url=https://www.usatoday.com/story/life/tv/columnist/2015/04/13/justified-fx-appreciation/25511161/|title=News & views: 'Justified' has made its mark|date=April 13, 2015|work=USA Today|access-date=May 9, 2016}}

Olyphant also served as a co-executive producer on Justified, working with Graham Yost and the writing team on some of the show's storylines and coming to the set on his days off to work with guest stars.{{cite web|url=https://www.hollywoodreporter.com/news/emmys-set-justified-as-fx-710447|title=Emmys: On the Set of 'Justified' as the FX Drama Heads Into Its Final Season|author=Bryn Elise Sandberg|date=June 10, 2014|work=The Hollywood Reporter|access-date=May 9, 2016}} He has described producing as "the greatest thing about this job". Yost has said of his producer credit: "Often on shows that really doesn't mean much. On this show it actually doesn't reflect the depth of his involvement, which would be an even bigger credit. Tim is the biggest reminder for everyone that we're in the Elmore Leonard world. And that it needs to be funny and dark and twisted, and it needs to speak with all of those voices at the same time." Justified was awarded a Peabody Award in 2011.{{cite web|url=http://www.peabodyawards.com/award-profile/justified|title=The Peabody Awards|access-date=May 9, 2016}}

Olyphant made occasional guest appearances on comedy television shows during Justified{{'}}s six-season run. He played a paper salesman in two episodes of the NBC comedy The Office (2010), after Mindy Kaling, a writer, producer and actress on the show, pushed for him to make a guest appearance.{{cite web|url=http://www.bullz-eye.com/television/interviews/2010/paul_lieberstein.htm|title=A chat with Paul Lieberstein, Paul Lieberstein interview, The Office|access-date=May 9, 2016}}{{cite web|url=http://dailytrojan.com/2010/10/31/olyphants-office-bit-sparks-internet-buzz/|title=Olyphant's Office bit sparks Internet buzz – Daily Trojan|first=Nick|last=Edmonds|work=Daily Trojan|date=October 31, 2010 |access-date=May 9, 2016}}{{cite web|url=https://www.vulture.com/2010/10/the_office_recap_the_olyphant.html|title=The Office Recap: The Olyphant in the Room|first=Phoebe|last=Reilly|work=Vulture|date=October 22, 2010 |access-date=May 9, 2016}} In 2012, he played a character billed as White Sushi Chef in an episode of the FX sitcom The League (2012){{cite web|url=https://www.cinemablend.com/television/League-Freeze-Out-Features-Timothy-Olyphant-Jason-Mantzoukas-48523.html|title=The League's Freeze Out Features Timothy Olyphant And Jason Mantzoukas|work=Cinemablend|date=October 24, 2012 |access-date=May 9, 2016}} and voiced a character in an episode of the FX animated series Archer.{{cite web|url=https://www.avclub.com/archer-the-wind-cries-mary-1798175593|title="The Wind Cries Mary" · Archer · TV Review Archer: "The Wind Cries Mary" · TV Club · The A.V. Club|website=The A.V. Club |date=January 25, 2013 |access-date=May 9, 2016}}{{cite web|url=http://www.slate.com/articles/arts/tv_club/features/2013/season_4_of_archer_reviewed/week_2/archer_season_4_the_wind_cries_mary_and_archer_s_facial_expressions_video.html|title=Archer Season 4: The Wind Cries Mary and Archer's facial expressions (VIDEO)|work=Slate Magazine|date=January 28, 2013 |access-date=May 9, 2016}} In 2013, he appeared as a love interest on the Fox comedy The Mindy Project. The guest appearance came about after he told Kaling that he wanted to appear on the show{{cite web|url=http://splitsider.com/2013/09/talking-to-ike-barinholtz-about-the-mindy-project-madtv-and-his-game-of-thrones-audition-tape/|title=Talking to Ike Barinholtz About 'The Mindy Project', 'MADtv', and His 'Game of Thrones' Audition Tape|work=Splitsider|date=September 12, 2013 |access-date=May 9, 2016}}{{cite web|url=http://www.eonline.com/news/457281/the-mindy-project-scoop-mindy-kaling-dishes-on-james-franco-juicy-danny-and-mindy-scenes-and-more|title=The Mindy Project Scoop: Mindy Kaling Dishes on James Franco, Juicy Danny Scenes and Wanting Channing Tatum – E! Online|date=September 10, 2013|work=E! Online|access-date=May 9, 2016}} and he later said he would have been happy to play his middle-aged skateboarder character for "years".{{cite web|url=https://www.avclub.com/the-mindy-project-sk8er-man-1798178568|title=The Mindy Project: "Sk8er Man"|first=Gwen|last=Ihnat|date=November 5, 2013|work=The A.V. Club|access-date=May 9, 2016}}{{cite web|url=http://www.modbee.com/news/local/article7266836.html|date=January 17, 2015|title=Modesto-raised Olyphant: Right time for 'Justified' to hit the trail|work=The Modesto Bee|first=Marijke|last=Rowland|access-date=May 9, 2016}}

Olyphant also worked on numerous films in between seasons of Justified. He voiced the Spirit of the West in the animated film Rango (2011).{{cite web|url=https://collider.com/timothy-olyphant-interview-i-am-number-four/|title=Timothy Olyphant Interview I AM NUMBER FOUR|date=October 16, 2010|work=Collider|access-date=May 9, 2016}}{{cite web|url=https://www.hollywoodreporter.com/news/rango-gore-verbinski-johnny-depp-286366|title=The Making of 'Rango': Gore Verbinski's Risky Ride Into Animation|first=Tim|last=Appelo|date=February 1, 2012|work=The Hollywood Reporter|access-date=May 9, 2016}} The character was a parody of Clint Eastwood's Man with No Name{{cite magazine|url=https://www.ew.com/article/2011/03/06/the-top-six-rango-riffs-on-classic-movies|title=Johnny Depp's 'Rango': Its top six riffs on classic movies|magazine=Entertainment Weekly|access-date=May 9, 2016}} and Olyphant was cast after director Gore Verbinski overheard him speaking on television: "I just sort of doubled back and looked through the door and was like, "That's our guy" ... Timothy has such a great quality to his voice."{{cite web|url=http://animatedviews.com/2012/director-gore-verbinski-wrangles-up-rango/|title=Director Gore Verbinski wrangles up Rango!|publisher=Animated Views|access-date=May 9, 2016}}{{cite web|url=https://www.cinemablend.com/new/Exclusive-Interview-Rango-Director-Gore-Verbinski-23461.html|title=Exclusive Interview: Rango Director Gore Verbinski|date=March 3, 2011 |access-date=May 9, 2016}}{{cite news|url=https://www.comingsoon.net/movies/features/74837-exclusive-gore-verbinski-on-re-animating-the-wild-west|title=Exclusive: Gore Verbinski on Re-Animating the Wild West|work=ComingSoon.net|date=March 3, 2011 |access-date=May 9, 2016 |last1=Lesnick |first1=Silas }} Olyphant appeared as a mentor to Alex Pettyfer's character in the science-fiction thriller I Am Number Four (2011). Justin Chang of Variety said he "brings some of his usual edge"{{cite web|url=https://variety.com/2011/film/reviews/i-am-number-four-1117944627/|title=I Am Number Four – Variety|first=Justin|last=Chang|work=Variety|date=February 16, 2011 |access-date=May 9, 2016}} but Betsy Sharkey of the Los Angeles Times felt he was "an untapped resource".{{cite web|url=https://www.latimes.com/entertainment/la-xpm-2011-feb-18-la-et-i-am-number-four-20110218-story.html|title=Movie review: 'I Am Number Four'|work=Los Angeles Times|date=February 18, 2011 |access-date=May 9, 2016}} Also in 2011, he voiced a character called Sergeant First Class "Grinch" in the video game, Call of Duty: Modern Warfare 3. In 2013, he appeared as Jeff Garlin's father in the independent comedy Dealin' with Idiots{{cite web|url=http://www.presspassla.com/dealin-idiots-exclusive-interview-jeff-garlin/|title=DEALIN' WITH IDIOTS, EXCLUSIVE INTERVIEW WITH JEFF GARLIN – Press Pass LA|work=Press Pass LA|date=July 11, 2013 |access-date=May 9, 2016}}{{cite web|url=https://www.pastemagazine.com/articles/2013/07/dealin-with-idiots.html|title=Dealin' with Idiots|work=pastemagazine.com|date=July 18, 2013 |access-date=May 9, 2016}} and took part in a one-off LACMA Live Read of the black comedy Raising Arizona (1987); he played Nicolas Cage's character while Amy Poehler played Holly Hunter's character.{{cite web|url=https://www.hollywoodreporter.com/news/amy-poehler-timothy-olyphant-patton-665747|title=Amy Poehler, Timothy Olyphant, Patton Oswalt Impress in LACMA Live Read's 'Raising Arizona'|first=Tim|last=Appelo|date=December 13, 2013|work=The Hollywood Reporter|access-date=May 9, 2016}}{{cite web|url=http://www.lamag.com/culturefiles/raising-arizona-and-raising-hell-at-lacmas-live-read/|title=Raising Arizona and Raising Hell at LACMA's Live Read|first=Drew|last=Tewksbury|date=December 13, 2013|work=Los Angeles Magazine|access-date=May 9, 2016}} In 2014, Olyphant starred with Tina Fey in the ensemble comedy-drama This Is Where I Leave You. Their characters were teenage sweethearts until an accident left him with a mild brain injury. The film received mixed reviews,{{cite web|url=https://www.nytimes.com/2014/09/19/movies/fractious-family-mourns-in-this-is-where-i-leave-you.html|title=Pallbearers Par Excellence|date=September 19, 2014|work=The New York Times|access-date=May 9, 2016}} with David Edelstein of Vulture commenting: "Over the course of his career, Olyphant has given life to head-slappingly bad material, and he does it again by simply underplaying."{{cite web|url=https://www.vulture.com/2014/09/movie-review-this-is-where-i-leave-you.html|title=Movie Review: This Is Where I Leave You – Vulture|first=David|last=Edelstein|work=Vulture|date=September 19, 2014 |access-date=May 9, 2016}}

Olyphant had a recurring guest role as a fictionalized version of himself in the Fox comedy The Grinder (2015–2016). His performance received positive critical notices,{{cite web|url=https://www.vulture.com/2015/11/grinder-recap-season-1-episode-8.html|title=The Grinder Recap: Give Me a Spritz|first=Allie|last=Pape|work=Vulture|date=November 25, 2015 |access-date=May 9, 2016}}{{cite web|url=https://www.vox.com/culture/2015/11/29/9813388/the-grinder-recap-review-fox|title=The Grinder is the year's funniest new show – Vox|first=Emily|last=VanDerWerff|date=November 29, 2015|work=Vox|access-date=May 9, 2016}}{{cite web|url=https://www.pastemagazine.com/articles/2015/11/the-grinder-review-giving-thanks-getting-justice.html|title=The Grinder Review: "Giving Thanks, Getting Justice"|work=pastemagazine.com|date=November 25, 2015 |access-date=May 9, 2016}}{{cite web|url=http://hiddenremote.com/2016/01/06/timothy-olyphant-just-won-grinder/|title=Timothy Olyphant Just Won 'The Grinder'|work=Hidden Remote|date=January 6, 2016 |access-date=May 9, 2016}} with USA Today{{'}}s Robert Bianco declaring it an "Emmy-deserving performance".{{cite web|url=https://www.usatoday.com/videos/life/tv/columnist/criticscorner/2016/01/04/78282272/|title=Critic's Corner: Timothy Olyphant on 'The Grinder'|date=January 4, 2016|work=USA Today|access-date=May 9, 2016}} The role won him the Critics' Choice Television Award for Best Guest Performer in a Comedy Series.{{cite magazine|url=https://www.ew.com/article/2016/01/17/critics-choice-awards-2016-winners-list|title=Critics' Choice Awards 2016 winners list - EW.com|magazine=Entertainment Weekly|access-date=May 9, 2016}}

In early 2016, Olyphant starred in the world premiere of Kenneth Lonergan's comedy Hold On to Me Darling at the off-Broadway Atlantic Theater Company. His character, Strings McCrane, is a self-absorbed country singer and actor who returns home to Tennessee following his mother's death.{{cite web|url=https://www.nytimes.com/aponline/2016/01/26/arts/ap-us-theater-timothy-olyphant.html|title='Justified' Star Timothy Olyphant Returns to the Stage|date=January 26, 2016|work=AP|access-date=May 9, 2016|via=The New York Times}}{{cite web|url=https://www.nytimes.com/2016/02/28/theater/q-and-a-timothy-olyphant-a-tough-lawman-goes-country-onstage.html|title=Q. and A.: Timothy Olyphant, a Tough Lawman, Goes Country Onstage|date=February 28, 2016|work=The New York Times|access-date=May 9, 2016}} Ben Brantley of the New York Times found him "entertainingly irritating" in a performance that "avoids the obvious route of histrionic posing"; "The startling, bona fide sorrow that Mr. Olyphant brings to [the final scene] truly illuminates everything that has come before."{{cite web|url=https://www.nytimes.com/2016/03/15/theater/review-kenneth-lonergans-hold-on-to-me-darling-a-study-of-bad-faith-and-behavior.html|title=Review: Kenneth Lonergan's 'Hold On to Me Darling,' a Study of Bad Faith (and Behavior)|date=March 15, 2016|work=The New York Times|access-date=May 9, 2016}} Frank Rizzo of Variety felt his performance was "a stunner, striking just the right notes of guilelessness, obliviousness and narcissism to make Strings one of the most appealing messes in a long time".{{cite web|url=https://variety.com/2016/legit/reviews/hold-on-to-me-darling-review-1201729265/|title='Hold on to Me Darling' Review: Timothy Olyphant Stars – Variety|first=Frank|last=Rizzo|work=Variety|date=March 15, 2016 |access-date=May 9, 2016}} David Rooney of The Hollywood Reporter felt the role "seems tailor-made for his laid-back swagger and sly humor ... Olyphant's natural charm ensures that Strings' unapologetic self-absorption remains more human than monstrous."{{cite web|url=https://www.hollywoodreporter.com/review/kenneth-lonergans-hold-me-darlng-874984|title=Kenneth Lonergan's 'Hold On to Me Darling': Theater Review|first=David|last=Rooney|date=March 14, 2016|work=The Hollywood Reporter|access-date=May 9, 2016}} He also played Henry, ex-husband of Sandy (Jennifer Aniston), in the universally-panned ensemble romantic comedy Mother's Day (2016);{{cite web|url=https://variety.com/2015/film/news/timothy-olyphant-shay-mitchell-britt-robertson-mothers-day-1201578994/|title='Justified,' 'Pretty Little Liars' Stars Join 'Mother's Day' – Variety|first=Dave|last=McNary|work=Variety|date=August 26, 2015 |access-date=May 9, 2016}} he appeared in Oliver Stone's Snowden (2016) as a CIA agent who befriends whistleblower Edward Snowden just prior to Snowden's fleeing to Russia, after publicly leaking classified US government information.{{cite web|url=https://www.avclub.com/article/timothy-olyphant-also-wants-oliver-stones-edward-s-215555|title=Timothy Olyphant also wants in on Oliver Stone's Edward Snowden movie|website=The A.V. Club |date=February 20, 2015 |access-date=May 9, 2016}}

In February 2017, Olyphant began starring in the Netflix horror-comedy Santa Clarita Diet, and also served as an executive producer for the series, which co-starred Drew Barrymore. Netflix renewed the series for a second season in March 2017{{cite news|last1=Schwindt|first1=Oriana|title=Netflix Renews 'Santa Clarita Diet' for Season 2|url=https://variety.com/2017/tv/news/santa-clarita-diet-renewed-season-2-netflix-1202018515/|access-date=April 30, 2017|work=Variety|date=March 29, 2017}}{{cite web|url=https://variety.com/2016/tv/news/santa-clarita-diet-drew-barrymore-timothy-olyphant-netflix-comedy-series-1201734047/|title='Santa Clarita Diet': Drew Barrymore & Timothy Olyphant Starring in Netflix Show |first=Elizabeth|last=Wagmeister|work=Variety|date=March 18, 2016 |access-date=May 9, 2016}} and for a third, ultimately final season in May 2018.{{cite news |last1=Otterson |first1=Joe |title='Santa Clarita Diet' Renewed for Season 3 at Netflix |url=https://variety.com/2018/tv/news/santa-clarita-diet-renewed-season-3-netflix-1202802036/ |access-date=March 23, 2019 |work=Variety |date=May 8, 2018}} Dark Was the Night, an independent drama in which he starred with Marisa Tomei, was filmed in 2015 and premiered at the 2018 Galway Film Fleadh.{{cite web|url=https://www.thewrap.com/marisa-tomei-timothy-olyphant-mireille-enos-to-star-in-indie-movie-behold-my-heart/|title=Marisa Tomei, Timothy Olyphant, Mireille Enos to Star in Indie Movie 'Behold My Heart'|first=Jeff|last=Sneider|date=December 8, 2015|work=TheWrap|access-date=May 9, 2016}}

In early 2016, HBO announced that David Milch was developing a two-hour film continuation of Deadwood.{{cite web|url=https://www.nytimes.com/2016/01/08/arts/television/hbo-eyeing-a-deadwood-return-and-game-of-thrones-extension.html|title=HBO Eyeing a 'Deadwood' Return and 'Game of Thrones' Extension|date=January 8, 2016|work=The New York Times|access-date=May 9, 2016}} The follow-up to the television series began production in October 2018.{{Cite news|url=https://www.hollywoodreporter.com/live-feed/deadwood-movie-starts-filming-majority-cast-returning-1158128|title='Deadwood' Movie Starts Filming with Majority of Cast Returning|work=The Hollywood Reporter|access-date=November 5, 2018}} Deadwood: The Movie premiered on HBO on May 31, 2019.{{cite web |last=Ausiello |first=Michael |date=March 21, 2019 |title=Deadwood: The Movie: Watch First Teaser Trailer for HBO Revival — Plus, Premiere Date Announced |url=https://tvline.com/2019/03/21/deadwood-movie-trailer-hbo-revival-video-premiere-date/ |access-date=March 21, 2019 |website=TVLine}}

In 2017, it was reported that Olyphant would play an FBI agent in the film Driven,{{cite news|last1=Lodderhose|first1=Diana|title=Jason Sudeikis, Lee Pace & Timothy Olyphant Gear Up For John DeLorean Pic 'Driven' — Cannes|url=https://deadline.com/2017/04/jason-sudeikis-timothy-olyphant-lee-pace-john-delorean-pic-cannes-driven-embankment-films-nick-hamm-1202079065/|access-date=April 30, 2017|website=Deadline Hollywood|date=April 28, 2017}} though he ultimately did not appear in the film. In 2018, Olyphant was cast as a voice actor for the stop-motion animated film Missing Link, which was released in April 2019.{{cite news |last1=Nickolai |first1=Nate |title=Hugh Jackman and Zach Galifianakis Join Forces In First 'Missing Link' Trailer for LAIKA |url=https://variety.com/2018/film/news/hugh-jackman-zach-galifianakis-missing-link-trailer-1203022802/ |access-date=March 23, 2019 |work=Variety |date=November 8, 2018}} He was also part of the large ensemble cast for the Quentin Tarantino semi-historical film Once Upon a Time in Hollywood, which was released in July 2019. Olyphant portrayed TV western star James Stacy in the film.{{cite news |last1=Coates |first1=Tyler |title=The Real-Life People Portrayed in Once Upon a Time in Hollywood|url=https://www.esquire.com/entertainment/movies/g26888375/once-upon-a-time-in-hollywood-cast-photos/ |access-date=March 23, 2019 |work=Esquire |date=March 21, 2019}}

In 2020, Olyphant joined the Star Wars franchise when he appeared as Cobb Vanth in the second season of the Disney+ space Western The Mandalorian.{{cite news|last1=VanArendonk|first1=Kathryn|title=Hot Damn, Timothy Olyphant in The Mandalorian|url=https://www.vulture.com/2020/10/timothy-olyphant-mandalorian-season-2.html|access-date=October 30, 2020|work=Vulture|date=October 30, 2020}} In 2022, he reprised the role in the first season of The Mandalorian spinoff series The Book of Boba Fett.{{cite news|last1=Hadadi|first1=Roxana|title=The Book of Boba Fett Catches Up With Our Two Favorite Boys|url=https://www.vulture.com/2022/02/the-book-of-boba-fett-cobb-vanth-grogu-from-the-desert-comes-a-stranger.html|access-date=February 13, 2022|work=Vulture|date=February 2, 2022}}

Olyphant returned to the role of Raylan Givens in the 2023 miniseries Justified: City Primeval.{{Cite web |last=Goldbart |first=Max |date=2022-01-14 |title=Timothy Olyphant To Return As Raylan Givens In 'Justified: City Primeval' As FX Greenlights Latest Elmore Leonard Adaptation |url=https://deadline.com/2022/01/fx-greenlights-latest-elmore-leonard-1234912732/ |access-date=2022-01-26 |website=Deadline}} On November 28, Deadline Hollywood revealed Olyphant has been cast as Kirsh in Noah Hawley’s upcoming Alien: Earth.{{Cite web |last=Andreeva |first=Nellie |date=2023-11-27 |title='Alien': Timothy Olyphant Joins Noah Hawley's FX Series |url=https://deadline.com/2023/11/timothy-olyphant-cast-alien-noah-hawley-fx-series-1235638841/ |access-date=2024-03-02 |website=Deadline Hollywood}}

Olyphant has been married to his college sweetheart Alexis Knief since 1991. They live in Westwood, Los Angeles, and have three children.{{cite news | last=Patterson |first=John |title=Timothy Olyphant: a law unto himself |newspaper=The Guardian |date=April 29, 2010 |url=https://www.theguardian.com/tv-and-radio/2010/apr/29/timothy-olyphant-justified |access-date=June 7, 2010}}{{cite news|url=http://www.womenshealthmag.com/sex-and-love/timothy-olyphant-interview|title=Timothy Olyphant Interview|work=Women's Health|access-date=May 9, 2016}} His daughter Vivian plays his character's daughter on Justified: City Primeval.{{cite magazine |last=Goldberg |first=Lesley |title=Justified Follow-Up Rounds Out Cast With Aunjanue Ellis, Boyd Holbrook, Marin Ireland and More |url=https://www.hollywoodreporter.com/tv/tv-news/justified-follow-up-rounds-out-cast-with-aunjanue-ellis-boyd-holbrook-marin-ireland-and-more-1235141596/ |magazine=The Hollywood Reporter |publisher=PMRC |date=May 5, 2022 |access-date=September 25, 2022 |archive-date=November 10, 2022 |archive-url=https://web.archive.org/web/20221110142305/https://www.hollywoodreporter.com/tv/tv-news/justified-follow-up-rounds-out-cast-with-aunjanue-ellis-boyd-holbrook-marin-ireland-and-more-1235141596/ |url-status=live }}

From 2006 to late 2008, Olyphant was the sports reporter for Joe Escalante's morning radio show on Los Angeles' Indie 103.1; film director David Lynch served as the show's weatherman.{{cite news|url=http://www.menshealth.com/guy-wisdom/the-secrets-of-my-success|title=The Success Plan for Every Man|work=Men's Health|access-date=May 9, 2016}}{{cite news|url=http://www.maxim.com/entertainment/we-want-answers-timothy-olyphant|title=We Want Answers: Timothy Olyphant|work=Maxim}}{{cite magazine|url=https://www.ew.com/article/2007/06/29/choose-your-sid|title=Choose your side: Timothy Olyphant or Josh Duhamel|magazine=Entertainment Weekly|access-date=May 9, 2016}} Olyphant phoned the station every weekday, delivering his reports in an unconventional style.{{cite web|url=https://www.thewrap.com/emmy-nominations-thewrap-picks-dream-contenders-for-outstanding-lead-actor-drama/|title=Emmy Nominations: TheWrap Picks Dream Contenders for Outstanding Lead Actor Drama|date=July 9, 2014|website=TheWrap|access-date=May 9, 2016}} Following the station's demise, he joked: "If you know of anyone looking for sports reports from an actor who is often just going off of what he recalls happened yesterday, or reading it directly from the newspaper, then I'm your guy."{{cite magazine|url=https://www.si.com/extra-mustard/2014/02/04/timothy-olyphant-justified-fx-interview-clippers-football|title="The Day the Clippers Win the Title…": A Q&A with "Justified" star Timothy Olyphant|author= Neumyer, Scott|date=February 4, 2014|magazine=Sports Illustrated|access-date=May 9, 2016}}

He is also a keen tennis player,{{cite web|url=https://www.tmz.com/2014/10/14/timothy-olyphant-pretty-badass-tennis-showdown-vs-gavin-rossdale-video/|title=Timothy Olyphant – Pretty Badass Tennis Showdown ... Vs. Gavin Rossdale [Video]|date=October 14, 2014|website=TMZ|access-date=May 9, 2016}}{{cite news|url=http://www.sun-sentinel.com/local/palm-beach/delray-beach/fl-drf-tennis-1203-20141203-story.html|title=Chris Evert Charities brings in big names to support programs |work=South Florida Sun-Sentinel|date=December 3, 2014|access-date=May 9, 2016}} and has participated in many pro-celebrity tournaments.{{cite web|url=https://www.turnerpr.com/spin-kitchen/8th-annual-k-swiss-desert-smash-celebrity-charity-tennis-event|title=8th ANNUAL K-SWISS DESERT SMASH CELEBRITY CHARITY TENNIS EVENT|website=TURNER PR|access-date=May 9, 2016}}{{cite magazine|url=https://www.vanityfair.com/style/2014/10/jimmy-goldstein-tennis-court-los-angeles|title=Jimmy Goldstein Opens UpL.A.'s Most Beautiful Tennis Court to Gavin Rossdale, Timothy Olyphant, and the MAK Center – Vanity Fair|author= Miller, Julie|magazine=Vanity Fair|access-date=May 9, 2016}}{{cite web|url=http://www.itatennis.com/AboutITA/News/Finals_Set_For_Inaugural_Oracle_ITA_Masters.htm|title=Finals Set For Inaugural Oracle/ITA Masters|website=itatennis|access-date=May 9, 2016}} He is a fan of the Los Angeles Clippers and the Los Angeles Dodgers, and he threw out the ceremonial first pitch at a Dodgers game in 2013.{{cite web|url=http://m.mlb.com/lad/video/topic/8010468/v28503675/olyphant-throws-out-the-first-pitch-at-dodger-stadium|archive-url=https://web.archive.org/web/20160223023649/http://m.mlb.com/lad/video/topic/8010468/v28503675/olyphant-throws-out-the-first-pitch-at-dodger-stadium|url-status=dead|archive-date=February 23, 2016|title=Olyphant throws first pitch|website=Los Angeles Dodgers|access-date=May 9, 2016}}

{{Reflist}}

{{Commons category|Timothy Olyphant}}

• {{IMDb name}}
• {{Emmys person|timothy-olyphant}}
• [https://web.archive.org/web/20160129044343/http://nerdist.com/nerdist-podcast-timothy-olyphant/ Nerdist Podcast: Timothy Olyphant]

{{Navboxes

|title = Awards for Timothy Olyphant

|list =

{{Critics' Choice Television Award for Best Guest Performer in a Comedy Series}}

{{Satellite Award for Best Actor – Television Series Drama}}

}}

{{Authority control}}

{{DEFAULTSORT:Olyphant, Timothy}}

Category:20th-century American male actors

Category:21st-century American male actors

Category:1968 births

Category:American male film actors

Category:American male swimmers

Category:American male television actors

Category:American male voice actors

Category:American people of Dutch descent

Category:American people of English descent

Category:American people of German descent

Category:American people of Irish descent

Category:American people of Russian-Jewish descent

Category:American people of Scottish descent

Category:Living people

Category:Male actors from California

Category:Male actors from Honolulu

Category:Male actors from Modesto, California

Timothy

Category:People from Westwood, Los Angeles

Category:Television producers from California

Category:Theatre World Award winners

Category:USC Roski School of Fine Arts alumni

Category:USC Trojans men's swimmers

Timothy Olyphant

Category:William Esper Studio alumni

Category:Male Western (genre) film actors