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He spent six months sword training before the filming of Troy, based on the Iliad.

In 2005, Pitt starred in the Doug Liman-directed action comedy Mr. Smith, in which a bored married couple discover that each is an assassin sent to kill the other.

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.

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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.

Pitt 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?

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.

Following the success of Seven, Pitt took a supporting role as Jeffrey Goines in Terry Gilliam's 1995 science-fiction film 12 Monkeys.

The movie received predominantly positive reviews, with Pitt praised in particular.They have six children together, three of whom were adopted internationally.In 2016, Jolie filed for a divorce from Pitt, which is currently pending.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).Pitt was credited on-screen as a producer; however, only Graham King was ruled eligible for the Oscar win.