Pitt's next leading role came in 2009 with the Quentin Tarantino-directed war film Inglourious Basterds, which premiered at the 2009 Cannes Film Festival. Pitt played Lieutenant Aldo Raine, an American resistance fighter battling Nazis in German-occupied France. The film was a box office hit, taking $311 million worldwide, and garnered generally favorable reviews. The film received multiple awards and nominations, including eight Academy Award nominations and seven MTV Movie Award nominations, including Best Male Performance for Pitt. He next voiced the superhero character Metro Man in the 2010 animated feature Megamind. Pitt produced and appeared in Terrence Malick's experimental drama The Tree of Life, co-starring Sean Penn, which won the Palme d'Or at the 2011 Cannes Film Festival. In a performance that attracted strong praise, he portrayed the Oakland Athletics general manager Billy Beane in the drama Moneyball, which is based on the 2003 book of the same name written by Michael Lewis. Moneyball received six Academy Award nominations including Best Picture and Best Actor for Pitt.
Reprising his role as Rusty Ryan in a third picture, Pitt starred in 2007's Ocean's Thirteen. While less lucrative than the first two films, this sequel earned $311 million at the international box office. Pitt's next film role was as American outlaw Jesse James in the 2007 Western drama The Assassination of Jesse James by the Coward Robert Ford, adapted from Ron Hansen's 1983 novel of the same name. Directed by Andrew Dominik and produced by Pitt's company Plan B Entertainment, the film premiered at the 2007 Venice Film Festival, with Pitt playing a "scary and charismatic" role, according to Lewis Beale of Film Journal International, and earning Pitt the Volpi Cup award for Best Actor at the 64th Venice International Film Festival. He eventually collected the award one year later at the 2008 festival. As of January 2019, it was his own favorite of his films.
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 InfoPitt was cast as Billy Canton, a drug addict who takes advantage of a young runaway (played by Juliette Lewis) in the 1990 NBC television movie Too Young to Die?, the story of an abused teenager sentenced to death for a murder. Ken Tucker, television reviewer for Entertainment Weekly wrote: "Pitt is a magnificent slimeball as her hoody boyfriend; looking and sounding like a malevolent John Cougar Mellencamp, he's really scary." The same year, Pitt co-starred in six episodes of the short-lived Fox drama Glory Days and took a supporting role in the HBO television film The Image. His next appearance came in the 1991 film Across the Tracks; Pitt portrayed Joe Maloney, a high school runner with a criminal brother, played by Rick Schroder. After years of supporting roles in film and frequent television guest appearances, Pitt attracted wider recognition in his supporting role in Ridley Scott's 1991 road film Thelma & Louise. He played J.D., a small-time criminal who befriends Thelma (Geena Davis). His love scene with Davis has been cited as the event that defined Pitt as a sex symbol. After Thelma & Louise, Pitt starred in the 1991 film Johnny Suede, a low-budget picture about an aspiring rock star, and the 1992 live-action/animated fantasy film Cool World, although neither furthered his career, having poor reviews and box office performance.
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 InfoWhile struggling to establish himself in Los Angeles, Pitt took lessons from acting coach Roy London. Pitt's acting career began in 1987, with uncredited parts in the films No Way Out (1987), No Man's Land (1987) and Less Than Zero (1987). In May 1987, his television debut came with a two-episode role on the NBC soap opera Another World. In November of the same year, Pitt had a guest appearance on the CBS sitcom Trial and Error and the ABC sitcom Growing Pains. He appeared in four episodes of the CBS primetime series Dallas between December 1987 and February 1988 as Randy, the boyfriend of Charlie Wade (played by Shalane McCall). Later in 1988, Pitt made a guest appearance on the Fox police drama 21 Jump Street. In the same year, the Yugoslavian–U.S. co-production The Dark Side of the Sun (1988) gave Pitt his first leading film role, as a young American taken by his family to the Adriatic to find a remedy for a skin condition. The film was shelved at the outbreak of the Croatian War of Independence, and was not released until 1997. Pitt made two motion picture appearances in 1989: the first in a supporting role in the comedy Happy Together; the second a featured role in the horror film Cutting Class, the first of Pitt's films to reach theaters. He made guest appearances on television series Head of the Class, Freddy's Nightmares, Thirtysomething, and (for a second time) Growing Pains.
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