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=== Rise to prominence (1999β2003) === In 1999, Pitt portrayed [[The Narrator (Fight Club)|Tyler Durden]] in ''[[Fight Club]]'',<ref>{{cite book |title=Fight Club |author=Chuck Palahniuk |author-link=Chuck Palahniuk |year=1996 |publisher=W. W. Norton & Company |isbn=978-0393039764 |page=25|title-link=Fight Club (novel)}}</ref><ref>{{cite news |url=https://www.smh.com.au/news/entertainment/film/the-business-of-being-brad/2008/12/13/1228585167094.html |title=The business of being Brad |author=Stephanie Bunbury |date=December 13, 2008 |work=[[The Sun-Herald]] |page=4 |access-date=May 13, 2009 |archive-url=https://web.archive.org/web/20090603061437/http://www.smh.com.au/news/entertainment/film/the-business-of-being-brad/2008/12/13/1228585167094.html |archive-date=June 3, 2009 |url-status=live}}</ref> a film adaptation of [[Chuck Palahniuk]]'s [[Fight Club (novel)|novel of the same name]], directed by [[David Fincher]].<ref name="fight">{{cite news |url=http://www.cnn.com/books/news/9910/19/fight.club.salon/index1.html |title='Fight Club': It 'Just sort of clicked' |author=Michael Sragow |date=October 19, 1999 |work=[[Salon.com]] |publisher=CNN |page=2 |access-date=December 31, 2008 |archive-url=https://web.archive.org/web/20161206061834/http://www.cnn.com/books/news/9910/19/fight.club.salon/index1.html |archive-date=December 6, 2016 |url-status=live}}</ref> Pitt prepared for the part with lessons in [[boxing]], [[taekwondo]], and [[grappling]].<ref>{{cite magazine |author=Stephen Garrett |title=Freeze Frame |magazine=[[Details (magazine)|Details]]|date=July 1999}}</ref> To look the part, Pitt consented to the removal of pieces of his front teeth which were restored when filming ended.<ref>{{cite magazine |author=Chris Nashawaty |url=https://www.ew.com/ew/article/0,,83604,00.html |title=Brad Pitt loses his teeth for a "Fight" |magazine=[[Entertainment Weekly]] |date=July 16, 1998 |access-date=February 25, 2009 |archive-url=https://web.archive.org/web/20140906114224/http://www.ew.com/ew/article/0,,83604,00.html |archive-date=September 6, 2014 |url-status=dead}}</ref> While promoting ''Fight Club'', Pitt said that the film explored not taking one's aggressions out on someone else but to "have an experience, take a punch more and see how you come out on the other end."<ref>{{cite news |url=http://www.cnn.com/SHOWBIZ/Movies/9910/14/fight.club/ |title=Brad Pitt spars with 'Fight Club' critics |author=Paul Vercammen |date=October 14, 1999 |publisher=[[CNN|CNN: Showbiz/Movies]] |access-date=December 7, 2008 |archive-url=https://web.archive.org/web/20090425062803/http://www.cnn.com/SHOWBIZ/Movies/9910/14/fight.club/ |archive-date=April 25, 2009 |url-status=live}}</ref> ''Fight Club'' premiered at the 1999 [[Venice International Film Festival]].<ref>{{cite news|url=https://news.google.com/newspapers?id=jAMzAAAAIBAJ&pg=6070,980986|title=Cruise, Kidman visit Venice Film Festival|work=The Free Lance-Star|date=September 4, 1999|page=26|access-date=September 23, 2013|archive-date=July 9, 2021|archive-url=https://web.archive.org/web/20210709183149/https://news.google.com/newspapers?id=jAMzAAAAIBAJ&pg=6070,980986|url-status=live}}</ref> Despite divided critical opinion on the film as a whole,<ref>{{cite web |url=https://www.metacritic.com/movie/fight-club/critic-reviews |title=Fight Club: What The Critics Said |website=[[Metacritic]] |access-date=February 28, 2010 |archive-url=https://web.archive.org/web/20110228045627/http://www.metacritic.com/movie/fight-club/critic-reviews |archive-date=February 28, 2011 |url-status=live}}</ref><ref>{{cite news |author=David Gritten |title=Premiere of ''Fight Club'' leaves critics slugging it out in Venice |work=The Ottawa Citizen |date=September 14, 1999}}</ref> Pitt's performance was widely praised. [[Paul Clinton]] of [[CNN]] noted the risky yet successful nature of the film,<ref>{{cite news |url=http://www.cnn.com/SHOWBIZ/Movies/9910/15/review.fight.club/ |title=Review: 'Fight Club' a two-fisted knockout |author=Paul Clinton |date=October 15, 1999 |publisher=[[CNN|CNN: Showbiz/Movies]] |access-date=March 29, 2009 |archive-url=https://web.archive.org/web/20090425062806/http://www.cnn.com/SHOWBIZ/Movies/9910/15/review.fight.club/ |archive-date=April 25, 2009 |url-status=live}}</ref> while ''Variety'' remarked upon Pitt's ability to be "cool, charismatic and more dynamically physical, perhaps than [...] his breakthrough role in ''Thelma and Louise''".<ref>{{cite news |url=https://www.variety.com/review/VE1117752116.html?categoryid=31&cs=1&p=0 |title=Fight Club Review |author=David Rooney |date=September 13, 1999 |work=Variety |access-date=October 15, 2008 |archive-url=https://web.archive.org/web/20081208200156/http://www.variety.com/review/VE1117752116.html?categoryid=31&cs=1&p=0 |archive-date=December 8, 2008 |url-status=live}}</ref> In spite of a worse-than-expected box office performance, ''Fight Club'' became a [[Cult following|cult classic]] after its DVD release in 2000.<ref>{{cite news |author=Dennis Lim |url=https://www.nytimes.com/2009/11/08/movies/homevideo/08lim.html |title='Fight Club' Fight Goes On |access-date=December 10, 2009 |date=November 8, 2009 |work=The New York Times |archive-url=https://archive.today/20120310035311/http://www.nytimes.com/2009/11/08/movies/homevideo/08lim.html |archive-date=March 10, 2012 |url-status=live}}</ref> [[File:Brad Pitt at Incirlik2.jpg|thumb|upright|left|Pitt in 2001]] Pitt was cast as an [[Irish Travellers|Irish Traveller]] [[boxing|boxer]] with a barely intelligible accent in [[Guy Ritchie]]'s 2000 gangster film ''[[Snatch (film)|Snatch]]''.<ref>{{cite news|url=http://archives.cnn.com/2001/SHOWBIZ/Movies/01/18/review.snatch/index.html |title='Snatch': Bloody kid stuff |author=Paul Tatara |date=January 18, 2001 |publisher=[[CNN|CNN: Showbiz/Movies]] |access-date=October 15, 2008 |url-status=dead |archive-url=https://web.archive.org/web/20110629045714/http://archives.cnn.com/2001/SHOWBIZ/Movies/01/18/review.snatch/index.html |archive-date=June 29, 2011}}</ref> Several reviewers were critical of ''Snatch''; however, most praised Pitt.<ref>{{cite web |url=https://www.metacritic.com/movie/snatch |title=Snatch (2001): Reviews |date=January 19, 2001 |website=[[Metacritic]] |access-date=December 31, 2008 |archive-url=https://web.archive.org/web/20101117021154/http://www.metacritic.com/movie/snatch |archive-date=November 17, 2010 |url-status=live}}</ref> Mick LaSalle of the ''San Francisco Chronicle'' said Pitt was "ideally cast as an Irishman whose accent is so thick even Brits can't understand him", going on to say that, before ''Snatch'', Pitt had been "shackled by roles that called for brooding introspection, but recently he has found his calling in black comic outrageousness and flashy extroversion;"<ref>{{cite news |url=http://www.sfgate.com/cgi-bin/article.cgi?file=/chronicle/archive/2001/01/19/DD166302.DTL&type=movies |title=Pitt Finds His Groove |author=Mick LaSalle |date=January 19, 2001 |work=San Francisco Chronicle |access-date=December 31, 2008 |archive-url=https://web.archive.org/web/20111018183017/http://www.sfgate.com/cgi-bin/article.cgi?file=%2Fchronicle%2Farchive%2F2001%2F01%2F19%2FDD166302.DTL&type=movies |archive-date=October 18, 2011 |url-status=live}}</ref> while [[Amy Taubin]] of ''[[The Village Voice]]'' claimed that "Pitt gets maximum comic mileage out of a one-joke role".<ref>{{cite news |url=http://www.villagevoice.com/2001-01-16/film/miscarried-justice-jejune-miscreants/2 |archive-url=https://web.archive.org/web/20121020215057/http://www.villagevoice.com/2001-01-16/film/miscarried-justice-jejune-miscreants/2/ |url-status=dead |archive-date=October 20, 2012 |title=Miscarried Justice; Jejune Miscreants |author=Amy Taubin |date=January 16, 2010 |work=[[The Village Voice]] |access-date=February 26, 2010}}</ref> The following year Pitt starred opposite [[Julia Roberts]] in the [[romantic comedy]] ''[[The Mexican]]'',<ref>{{cite news|author=Jay Boyar|title=Runaway Ride β 'The Mexican' Is Freewheeling Fun From Julia Roberts, Brad Pitt|date=March 2, 2001|work=[[Orlando Sentinel]]|page=21}}</ref> a film that garnered a range of reviews<ref>{{cite web |url=https://www.metacritic.com/movie/the-mexican |title=Mexican, The (2001): Reviews |date=March 2, 2001 |website=[[Metacritic]] |access-date=March 26, 2009 |archive-url=https://web.archive.org/web/20110921132757/http://www.metacritic.com/movie/the-mexican |archive-date=September 21, 2011 |url-status=live}}</ref> but enjoyed box office success.<ref name="earnings" /> Pitt's next role, in 2001's $143 million-grossing [[Cold War]] thriller ''[[Spy Game]]'',<ref name="earnings" /> was as Tom Bishop, an operative of the [[Central Intelligence Agency|CIA]]'s [[Special Activities Division]], mentored by [[Robert Redford]]'s character.<ref>{{cite news|url=http://www.villagevoice.com/2001-11-27/film/international-men-of-history/1 |title=International Men of History |author=Mark Holcomb |date=November 27, 2001 |work=[[The Village Voice]] |access-date=October 15, 2008 |page=1 |url-status=dead |archive-url=https://web.archive.org/web/20110825223940/http://www.villagevoice.com/2001-11-27/film/international-men-of-history/1/ |archive-date=August 25, 2011}}</ref> Mark Holcomb of [[Salon.com]] enjoyed the film, although he noted that neither Pitt nor Redford provided "much of an emotional connection for the audience".<ref>{{cite news |url=http://www.salon.com/2001/11/21/spy_game/ |title=Spy Game |author=Charles Taylor |date=November 21, 2001 |work=[[Salon.com]] |page=2 |access-date=February 25, 2009 |archive-url=https://web.archive.org/web/20170924093548/http://www.salon.com/2001/11/21/spy_game/ |archive-date=September 24, 2017 |url-status=live}}</ref> On November 22, 2001, Pitt made a guest appearance in the [[The One with the Rumor|eighth season]] of the television series ''[[Friends]]'', playing a man with a grudge against [[Rachel Green]], played by [[Jennifer Aniston]], to whom Pitt was married at the time.<ref>{{cite news |url=http://news.bbc.co.uk/1/hi/entertainment/1668756.stm |title=Pitt joins Aniston in Friends |access-date=September 23, 2013 |date=November 21, 2001 |work=[[BBC News]] |archive-date=March 21, 2022 |archive-url=https://web.archive.org/web/20220321195950/http://news.bbc.co.uk/2/hi/entertainment/1668756.stm |url-status=live}}</ref> For this performance he was nominated for an [[Primetime Emmy Award|Emmy Award]] in the category of [[Primetime Emmy Award for Outstanding Guest Actor β Comedy Series|Outstanding Guest Actor in a Comedy Series]].<ref>{{cite magazine |url=https://www.ew.com/ew/article/0,,321601,00.html |title=Trophy Time |author=Gary Susman |date=July 17, 2002 |magazine=Entertainment Weekly |access-date=April 22, 2009 |archive-url=https://web.archive.org/web/20090605233103/http://www.ew.com/ew/article/0,,321601,00.html |archive-date=June 5, 2009 |url-status=dead}}</ref> In December 2001, Pitt played [[Rusty Ryan (character)|Rusty Ryan]] in the heist film ''[[Ocean's Eleven (2001 film)|Ocean's Eleven]]'', a remake of the 1960 [[Ocean's Eleven (1960 film)|Rat Pack original]]. He joined an ensemble cast including [[George Clooney]], [[Matt Damon]], [[Andy GarcΓa]], and Julia Roberts.<ref name="oceans">{{cite news |url=http://rogerebert.suntimes.com/apps/pbcs.dll/article?AID=/20011207/REVIEWS/112070302/1023 |title=Ocean's Eleven |author=Roger Ebert |date=December 7, 2001 |work=Chicago Sun-Times |access-date=October 15, 2008 |archive-url=https://web.archive.org/web/20130402202645/http://rogerebert.suntimes.com/apps/pbcs.dll/article?AID=%2F20011207%2FREVIEWS%2F112070302%2F1023 |archive-date=April 2, 2013 |url-status=live}}</ref> Well received by critics, ''Ocean's Eleven'' was highly successful at the box office, earning $450 million worldwide.<ref name="earnings" /> Pitt appeared in two episodes of MTV's reality series ''[[Jackass (franchise)|Jackass]]'' in February 2002, first running through the streets of Los Angeles with several cast members in gorilla suits,<ref>{{cite episode |title=Night Monkey 2 (with Brad Pitt) |series=[[Jackass (franchise)|Jackass]]|network=MTV |airdate=February 10, 2002 |season=3 |number=8 |minutes=22β23}}</ref> and in a subsequent episode participating in his own staged abduction.<ref>{{cite episode |title=The Abduction (with Brad Pitt) |series=[[Jackass (franchise)|Jackass]]|network=MTV |airdate=February 17, 2002 |season=3 |number=9 |minutes=22β23}}</ref> In the same year, Pitt had a cameo role in George Clooney's directorial debut ''[[Confessions of a Dangerous Mind (film)|Confessions of a Dangerous Mind]]''.<ref>{{cite news|url=http://archives.cnn.com/2002/SHOWBIZ/Movies/12/30/barris.cnna/ |title=Chuck Barris' 'Dangerous Mind' |author=Bill Hemmer |date=December 30, 2002 |publisher=[[CNN|CNN: Showbiz/Movies]] |access-date=July 24, 2009 |url-status=dead |archive-url=https://web.archive.org/web/20110629045725/http://archives.cnn.com/2002/SHOWBIZ/Movies/12/30/barris.cnna/ |archive-date=June 29, 2011}}</ref> He took on his first voice-acting roles in 2003, speaking as the titular character of the [[DreamWorks Pictures|DreamWorks]] animated film ''[[Sinbad: Legend of the Seven Seas]]''<ref>{{cite news |url=https://movies.nytimes.com/movie/review?res=9D01E7DD123AF931A35754C0A9659C8B63 |title=Sinbad: Legend of the Seven Seas review |author=Elvis Mitchell |author-link=Elvis Mitchell |date=July 2, 2003 |work=The New York Times |access-date=October 29, 2008 |archive-url=https://web.archive.org/web/20120117222921/http://movies.nytimes.com/movie/review?res=9D01E7DD123AF931A35754C0A9659C8B63 |archive-date=January 17, 2012 |url-status=live}}</ref> and playing [[Boomhauer]]'s brother, [[Patch Boomhauer|Patch]], in an episode of the animated television series ''[[King of the Hill]]''.<ref>{{cite episode |title=Patch Boomhauer |series=King of the Hill |credits=J.B. Cooke, Anthony Lioi |network=Fox |airdate=November 2, 2003 |season=8 |number=150 |minutes=22}}</ref>
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