Pitt's next appearance was in the 2008 black comedy Burn After Reading, his first collaboration with the Coen brothers. The film received a positive reception from critics, with The Guardian calling it "a tightly wound, slickly plotted spy comedy", noting that Pitt's performance was one of the funniest. He was later cast as Benjamin Button, the lead in David Fincher's 2008 film The Curious Case of Benjamin Button, a loosely adapted version of a 1921 short story by F. Scott Fitzgerald. The story follows a man who is born an octogenarian and ages in reverse, with Pitt's "sensitive" performance making Benjamin Button a "timeless masterpiece", according to Michael Sragow of The Baltimore Sun. The performance earned Pitt his first Screen Actors Guild Award nomination, as well as a fourth Golden Globe and second Academy Award nomination, all in the category for Best Actor. The film received thirteen Academy Award nominations in total, and grossed $329 million at the box office worldwide.
Pitt took the role of Paul Maclean in the 1992 biographical film A River Runs Through It, directed by Robert Redford. His portrayal of the character was described by People's Janet Mock as a career-making performance, proving that Pitt could be more than a "cowboy-hatted hunk." He has admitted to feeling under pressure when making the film and thought it was one of his "weakest performances ... It's so weird that it ended up being the one that I got the most attention for." Pitt believed that he benefited from working with such a talented cast and crew. 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." Pitt also garnered attention for a brief appearance in the cult hit True Romance as a stoner named Floyd, providing much needed comic relief to the action film. He capped the year by winning a ShoWest Award for Male Star of Tomorrow.
More InfoPitt took the role of Paul Maclean in the 1992 biographical film A River Runs Through It, directed by Robert Redford. His portrayal of the character was described by People's Janet Mock as a career-making performance, proving that Pitt could be more than a "cowboy-hatted hunk." He has admitted to feeling under pressure when making the film and thought it was one of his "weakest performances ... It's so weird that it ended up being the one that I got the most attention for." Pitt believed that he benefited from working with such a talented cast and crew. 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." Pitt also garnered attention for a brief appearance in the cult hit True Romance as a stoner named Floyd, providing much needed comic relief to the action film. He capped the year by winning a ShoWest Award for Male Star of Tomorrow.
More InfoReprising 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.
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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