For his next film, Pitt starred opposite Cate Blanchett in Alejandro González Iñárritu's multi-narrative drama Babel (2006). Pitt's performance was critically well-received, and the Seattle Post-Intelligencer said that he was credible and gave the film visibility. Pitt later said he regarded taking the part as one of the best decisions of his career. The film was screened at a special presentation at the 2006 Cannes Film Festival and was later featured at the 2006 Toronto International Film Festival. Babel received seven Academy and Golden Globe award nominations, winning the Best Drama Golden Globe, and earned Pitt a nomination for the Best Supporting Actor Golden Globe. That same year, Pitt's company Plan B Entertainment produced The Departed, which won the Academy Award for Best Picture. Pitt was credited on-screen as a producer; however, only Graham King was ruled eligible for the Oscar win.
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 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.
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.
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 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.
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