In 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.
While 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.
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.
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 starred in Fight Club (1999) and the heist film Ocean's Eleven (2001), as well as its sequels, Ocean's Twelve (2004) and Ocean's Thirteen (2007). His greatest commercial successes have been Ocean's Eleven (2001), Troy (2004), Mr. & Mrs. Smith (2005), World War Z (2013), and Once Upon a Time in Hollywood (2019), for which he won a second Golden Globe Award and the Academy Award for Best Supporting Actor. Pitt's other Academy Award nominated performances were in The Curious Case of Benjamin Button (2008) and Moneyball (2011). He produced The Departed (2006) and 12 Years a Slave (2013), both of which won the Academy Award for Best Picture, and also The Tree of Life (2011), Moneyball (2011), and The Big Short (2015), all of which were nominated for Best Picture.
More InfoPitt 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.
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