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 InfoPitt was cast as an Irish Gypsy boxer with a barely intelligible accent in Guy Ritchie's 2000 gangster film Snatch. Several reviewers were critical of Snatch; however, most praised Pitt. Mick LaSalle of the San Francisco Chronicle said Pitt was "ideally cast as an Irishman whose accent is so thick even Brits can't understand him", going on to say that, before Snatch, Pitt had been "shackled by roles that called for brooding introspection, but recently he has found his calling in black comic outrageousness and flashy extroversion;" while Amy Taubin of The Village Voice claimed that "Pitt gets maximum comic mileage out of a one-joke role". The following year Pitt starred opposite Julia Roberts in the romantic comedy The Mexican, a film that garnered a range of reviews but enjoyed box office success. Pitt's next role, in 2001's $143 million-grossing Cold War thriller Spy Game, was as Tom Bishop, an operative of the CIA's Special Activities Division, mentored by Robert Redford's character. Mark Holcomb of Salon.com enjoyed the film, although he noted that neither Pitt nor Redford provided "much of an emotional connection for the audience".
More InfoThe 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 InfoIn 1995, Pitt starred alongside Morgan Freeman and Gwyneth Paltrow in the crime thriller Seven, playing a detective on the trail of a serial killer. Pitt called it a great movie and declared the part would expand his acting horizons. He expressed his intent to move on from "this 'pretty boy' thing [...] and play someone with flaws." His performance was critically well received, with Variety saying that it was screen acting at its best, further remarking on Pitt's ability to turn in a "determined, energetic, creditable job" as the detective. Seven earned $327 million at the international box office. 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. Janet Maslin of The New York Times called Twelve Monkeys "fierce and disturbing" and remarked on Pitt's "startlingly frenzied performance", concluding that he "electrifies Jeffrey with a weird magnetism that becomes important later in the film." He won a Golden Globe Award for Best Supporting Actor for the film and received his first Academy Award nomination for Best Supporting Actor.
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 InfoWe don't show ads. Help us keep it that way.