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He gave critically acclaimed performances in the crime thriller Seven and the science fiction film 12 Monkeys (both 1995), the latter earning him a Golden Globe Award for Best Supporting Actor and an Academy Award nomination.
Pitt starred in the cult film Fight Club (1999) and the heist film Ocean's Eleven (2001) and its sequels, Ocean's Twelve (2004) and Ocean's Thirteen (2007). Pitt received his second and third Academy Award nominations for his leading performances in The Curious Case of Benjamin Button (2008) and Moneyball (2011).
As graduation approached, Pitt did not feel ready to settle down. 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.
He loved films—"a portal into different worlds for me"—and, since films were not made in Missouri, he decided to go to where they were made. The film was shelved at the outbreak of the Croatian War of Independence, and was not released until 1997.
His first leading roles in big-budget productions came with the drama films A River Runs Through It (1992) and Legends of the Fall (1994), and horror film Interview with the Vampire (1994).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." 1994 marked a significant turning point in Pitt's career. When directors play up his cocky, hunkish, folksy side ... But there's nothing about him that suggests inner torment or even self-awareness, which makes him a boring Louis." based on a novel by the same name by Jim Harrison, set in the American West during the first four decades of the twentieth century.For a number of years, he was cited as the world's most attractive man by various media outlets, and his personal life is the subject of wide publicity.Divorced from actress Jennifer Aniston after five years of marriage, he married actress Angelina Jolie in 2014.
, the story of an abused teenager sentenced to death for a murder.