Later that year, he led as Austrian mountaineer Heinrich Harrer in the Jean-Jacques Annaud film Seven Years in Tibet.[61] 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.[62] 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.[63] 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."[64] Roger Ebert remarked, "Pitt is a fine actor, but this performance is a miscalculation."[65]

Pitt was cast as an 💵 Irish Traveller boxer with a barely intelligible accent in Guy Ritchie's 2000 gangster film Snatch.[78] Several reviewers were critical of 💵 Snatch; however, most praised Pitt.[79] 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;"[80] while Amy Taubin of The Village Voice claimed that "Pitt gets maximum comic mileage out of a one-joke 💵 role".[81]

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",[114] noting 💵 that Pitt's performance was one of the funniest.[114] 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,[115] with Pitt's "sensitive" performance making 💵 Benjamin Button a "timeless masterpiece", according to Michael Sragow of The Baltimore Sun.[116] The performance earned Pitt his first Screen 💵 Actors Guild Award nomination,[117] as well as a fourth Golden Globe and second Academy Award nomination,[45][118] all in the category 💵 for Best Actor. The film received thirteen Academy Award nominations, and grossedR$329 million at the box office worldwide.[32]

In 2024, Pitt 💵 starred in Bullet Train, directed by David Leitch,[159] and reunited with his Once Upon a Time in Hollywood co-star Margot 💵 Robbie in Babylon, directed by Damien Chazelle.[160] In September 2024, it was revealed that he will reteam with George Clooney 💵 in a thriller film written and directed by Jon Watts.[161] On January 5, 2024, he signed on to star in 💵 and produce a racing film on Formula One, directed by Joseph Kosinski,[162] for which he will earnR$30 million.[163]