Pitt had two major film roles in 2004, starring as Achilles in Troy, and reprising his role, Rusty Ryan, in the sequel Ocean's Twelve. He spent six months sword training before the filming of Troy, based on the Iliad. An on-set injury to his Achilles tendon delayed production on the picture for several weeks. Stephen Hunter of The Washington Post stated that Pitt excelled at such a demanding role. Troy was the first film produced by Plan B Entertainment, a film production company he had founded two years earlier with Jennifer Aniston and Brad Grey, CEO of Paramount Pictures. Ocean's Twelve earned $362 million worldwide, and Pitt and Clooney's dynamic was described by CNN's Paul Clinton as "the best male chemistry since Paul Newman and Robert Redford." In 2005, Pitt starred as John Smith in the Doug Liman-directed action comedy Mr. & Mrs. Smith, in which a bored married couple discover that each is an assassin sent to kill the other. The feature received reasonable reviews but was generally lauded for the chemistry between Pitt and Angelina Jolie, who played his character's wife Jane Smith. The Star Tribune noted that "while the story feels haphazard, the movie gets by on gregarious charm, galloping energy and the stars' thermonuclear screen chemistry". Mr. & Mrs. Smith earned $478 million worldwide, making it one of the biggest hits of 2005.
Pitt took the role of Paul Maclean in the 1992 biographical film A River Runs Through It, directed by Robert Redford. His portrayal of the character was described by People's Janet Mock as a career-making performance, proving that Pitt could be more than a "cowboy-hatted hunk." He has admitted to feeling under pressure when making the film and thought it was one of his "weakest performances ... It's so weird that it ended up being the one that I got the most attention for." Pitt believed that he benefited from working with such a talented cast and crew. He compared working with Redford to playing tennis with a superior player, saying "when you play with somebody better than you, your game gets better." In 1993, Pitt reunited with Juliette Lewis for the road film Kalifornia. He played Early Grayce, a serial killer and the boyfriend of Lewis's character in a performance described by Peter Travers of Rolling Stone as "outstanding, all boyish charm and then a snort that exudes pure menace." Pitt also garnered attention for a brief appearance in the cult hit True Romance as a stoner named Floyd, providing much needed comic relief to the action film. He capped the year by winning a ShoWest Award for Male Star of Tomorrow.
More InfoThe following year, he had a role in the legal drama Sleepers (1996), based on Lorenzo Carcaterra's novel of the same name. The film received mixed reviews. In the 1997 film The Devil's Own Pitt starred, opposite Harrison Ford, as the Irish Republican Army terrorist Rory Devany, a role for which he was required to learn an Irish accent. Critical opinion was divided on his accent; "Pitt finds the right tone of moral ambiguity, but at times his Irish brogue is too convincing – it's hard to understand what he's saying", wrote the San Francisco Chronicle. The Charleston Gazette opined that it had favored Pitt's accent over the movie. The Devil's Own grossed $140 million worldwide, but was a critical failure. Later that year, he led as Austrian mountaineer Heinrich Harrer in the Jean-Jacques Annaud film Seven Years in Tibet. Pitt trained for months for the role, which demanded significant mountain climbing and trekking practice, including rock climbing in California and the European Alps with his co-star David Thewlis. The film received mostly negative reviews, and was generally considered a disappointment. Pitt had the lead role in 1998's fantasy romance film Meet Joe Black. He portrayed a personification of death inhabiting the body of a young man to learn what it is like to be human. The film received mixed reviews, and many were critical of Pitt's performance. According to Mick LaSalle of the San Francisco Chronicle, Pitt was unable to "make an audience believe that he knows all the mysteries of death and eternity." Roger Ebert stated "Pitt is a fine actor, but this performance is a miscalculation."
More InfoPitt was cast as an Irish Gypsy boxer with a barely intelligible accent in Guy Ritchie's 2000 gangster film Snatch. Several reviewers were critical of Snatch; however, most praised Pitt. 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;" while Amy Taubin of The Village Voice claimed that "Pitt gets maximum comic mileage out of a one-joke role". The following year Pitt starred opposite Julia Roberts in the romantic comedy The Mexican, a film that garnered a range of reviews but enjoyed box office success. Pitt's next role, in 2001's $143 million-grossing Cold War thriller Spy Game, was as Tom Bishop, an operative of the CIA's Special Activities Division, mentored by Robert Redford's character. 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".
More InfoIn 1999, Pitt portrayed Tyler Durden in Fight Club, a film adaptation of Chuck Palahniuk's novel of the same name, directed by David Fincher. Pitt prepared for the part with lessons in boxing, taekwondo, and grappling. To look the part, Pitt consented to the removal of pieces of his front teeth which were restored when filming ended. 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." Fight Club premiered at the 1999 Venice International Film Festival. Despite divided critical opinion on the film as a whole, Pitt's performance was widely praised. Paul Clinton of CNN noted the risky yet successful nature of the film, while Variety remarked upon Pitt's ability to be "cool, charismatic and more dynamically physical, perhaps than [...] his breakthrough role in Thelma and Louise". In spite of a worse-than-expected box office performance, Fight Club became a cult classic after its DVD release in 2000.
More InfoOn November 22, 2001, Pitt made a guest appearance in the 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. For this performance he was nominated for an Emmy Award in the category of Outstanding Guest Actor in a Comedy Series. In December 2001, Pitt played Rusty Ryan in the heist film Ocean's Eleven, a remake of the 1960 Rat Pack original. He joined an ensemble cast including George Clooney, Matt Damon, Andy García, and Julia Roberts. Well received by critics, Ocean's Eleven was highly successful at the box office, earning $450 million worldwide. Pitt appeared in two episodes of MTV's reality series Jackass in February 2002, first running through the streets of Los Angeles with several cast members in gorilla suits, and participating in his own staged abduction in another episode. In the same year, Pitt had a cameo role in George Clooney's directorial debut Confessions of a Dangerous Mind. He took on his first voice-acting roles in 2003, speaking as the titular character of the DreamWorks animated film Sinbad: Legend of the Seven Seas and playing Boomhauer's brother, Patch, in an episode of the animated television series King of the Hill.
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