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.
The following year, he had a role in the legal drama Sleepers (1996), based on Lorenzo Carcaterra's novel of the same name. The film received mixed reviews. In the 1997 film The Devil's Own Pitt starred, opposite Harrison Ford, as the Irish Republican Army terrorist Rory Devany, a role for which he was required to learn an Irish accent. Critical opinion was divided on his accent; "Pitt finds the right tone of moral ambiguity, but at times his Irish brogue is too convincing – it's hard to understand what he's saying", wrote the San Francisco Chronicle. The Charleston Gazette opined that it had favored Pitt's accent over the movie. The Devil's Own grossed $140 million worldwide, but was a critical failure. Later that year, he led as Austrian mountaineer Heinrich Harrer in the Jean-Jacques Annaud film Seven Years in Tibet. Pitt trained for months for the role, which demanded significant mountain climbing and trekking practice, including rock climbing in California and the European Alps with his co-star David Thewlis. The film received mostly negative reviews, and was generally considered a disappointment. Pitt had the lead role in 1998's fantasy romance film Meet Joe Black. He portrayed a personification of death inhabiting the body of a young man to learn what it is like to be human. The film received mixed reviews, and many were critical of Pitt's performance. According to Mick LaSalle of the San Francisco Chronicle, Pitt was unable to "make an audience believe that he knows all the mysteries of death and eternity." Roger Ebert stated "Pitt is a fine actor, but this performance is a miscalculation."
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 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 Info1994 marked a significant turning point in Pitt's career. Starring as the vampire Louis de Pointe du Lac in the horror film Interview with the Vampire: The Vampire Chronicles, based on Anne Rice's 1976 novel of the same name, he was part of an ensemble cast that included Tom Cruise, Kirsten Dunst, Christian Slater, and Antonio Banderas. Despite his winning two MTV Movie Awards at the 1995 ceremony, his performance was poorly received. According to the Dallas Observer, "Brad Pitt [...] is a large part of the problem [in the film]. When directors play up his cocky, hunkish, folksy side [...] he's a joy to watch. But there's nothing about him that suggests inner torment or even self-awareness, which makes him a boring Louis." Following the release of Interview with the Vampire, Pitt starred in Legends of the Fall (1994), 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. Portraying Tristan Ludlow, son of Colonel William Ludlow (Anthony Hopkins) a Cornish immigrant, Pitt received his first Golden Globe Award nomination, in the Best Actor category. Aidan Quinn and Henry Thomas co-starred as Pitt's brothers. Although the film's reception was mixed, many film critics praised Pitt's performance. Janet Maslin of The New York Times said, "Pitt's diffident mix of acting and attitude works to such heartthrob perfection it's a shame the film's superficiality gets in his way." The Deseret News predicted that Legends of the Fall would solidify Pitt's reputation as a lead actor.
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