At the very beginning of the 92nd Academy Awards, the ever-dapper Brad Pitt nabbed the Oscar for best supporting actor for his role as stuntman Cliff Booth in Quentin Tarantino's Once Upon a Time in Hollywood. It's, surprisingly to some, his first acting win, one which seemed all but inevitable — his role has received buzz throughout awards season, earning him a BAFTA and a Golden Globe. Before OUATIH, Pitt had been a flagship name in modern cinema, of course, and this is far from being his first time in the Oscars rodeo. Pitt has been nominated for seven Oscars and has technically won two.
Before his Cliff Booth win, the seasoned actor had been nominated for best supporting actor in 12 Monkeys (1996) as well as best actor in The Curious Case of Benjamin Button (2009) and Moneyball (2012). His films 12 Years a Slave (2014) and The Big Short (2016) had also been nominated for best picture. For these last two, Pitt worked on the off-screen side of things as a producer.
In 2014, Pitt won in that capacity when Steve McQueen's 12 Years a Slave picked up the best picture award at the Oscars. Pitt played a small part in the movie as Canadian carpenter Samuel Bass. As a producer, he was able to hold his very own gold statue when the film won at the close of the night. Now, after decades in the industry, the 56-year-old finally has an award for acting — though, ironically in the film, he portrays the stuntman to Leonardo DiCaprio's actor character. While this is his second win, we're sure that we'll be seeing more of Pitt over the years — he already has a ton of producing credits for upcoming projects.