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.
On 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 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 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 had two major film roles in 2004, starring as Achilles in Troy, and reprising his role, Rusty Ryan, in the sequel Ocean's Twelve. He spent six months sword training before the filming of Troy, based on the Iliad. An on-set injury to his Achilles tendon delayed production on the picture for several weeks. Stephen Hunter of The Washington Post stated that Pitt excelled at such a demanding role. Troy was the first film produced by Plan B Entertainment, a film production company he had founded two years earlier with Jennifer Aniston and Brad Grey, CEO of Paramount Pictures. Ocean's Twelve earned $362 million worldwide, and Pitt and Clooney's dynamic was described by CNN's Paul Clinton as "the best male chemistry since Paul Newman and Robert Redford." In 2005, Pitt starred as John Smith in the Doug Liman-directed action comedy Mr. & Mrs. Smith, in which a bored married couple discover that each is an assassin sent to kill the other. The feature received reasonable reviews but was generally lauded for the chemistry between Pitt and Angelina Jolie, who played his character's wife Jane Smith. The Star Tribune noted that "while the story feels haphazard, the movie gets by on gregarious charm, galloping energy and the stars' thermonuclear screen chemistry". Mr. & Mrs. Smith earned $478 million worldwide, making it one of the biggest hits of 2005.
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.
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