Brad Pitt Wins Oscar for Once Upon a Time in Hollywood

Brad Pitt just won his first acting Oscar for playing Cliff Booth in Once Upon a Time... in Hollywood. Somewhere Brandy the dog is smiling.

Leonardo DiCaprio and Brad Pitt in Once Upon a Time in Hollywood

After spending a career looking for credibility, we wonder what Rick Dalton would think of his stuntman being the one to take home an Oscar? To be fair, it wasn’t actually Cliff Booth who earned the little gold man at tonight’s Academy Awards. Nay, that honor belonged exclusively to Brad Pitt who picks up the first acting Oscar of his career in Once Upon a Time… in Hollywood.

One of the biggest movie stars of his generation, Pitt also cemented his status as a screen legend when his name was read for the Best Supporting Actor category during the 92nd Academy Awards. Strolling up to the stage early in the night, Pitt completed what has been an impressive circuit during awards season.

Pitt marked his victory taking a hilarious jab at the expense of the Republicans in the U.S. Senate when he noted ABC only gave him 45 seconds to make a speech. He said, “That’s 45 more seconds than the Senate gave John Bolton this week. I’m thinking maybe next time Quentin does a movie about it, and in the end the adults do the right thing.” That’d be a nice change of pace, eh?

Pitt’s win for Best Supporting Actor is not exactly the world’s biggest surprise. He has after all had a clean sweep of that category during awards season, picking up equivalent gongs from the Screen Actors Guild, Golden Globes, Critics Choice Awards, and BAFTA. But for almost everyone who watched Quentin Tarantino’s ninth and allegedly penultimate film, it was a much deserved series of surprises for the laconic star and his perhaps most laconic performance to date.

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Nominated three times in the past for acting roles, Pitt’s transformation into a Hollywood statesman appears complete with this win, not least of all because it isn’t actually his first Oscar. Indeed, he previously won an Oscar in 2014 for producing the Best Picture winner, 12 Years a Slave. Some might wonder if his newly established role as a Hollywood producer and tastemaker will be as much a part of his legacy as his acting career.

In recent years, he has invested in bringing a slew of diverse voices to the center stage, including Steve McQueen on 12 Years, Ava DuVernay on Selma, Bong Joon-ho on Okja, Barry Jenkins on Moonlight and If Beale Street Could Talk, Adam McKay on The Big Short and Vice, Joe Talbot on The Last Black Man in San Francisco, and Andrew Dominik on The Assassination of Jesse James by the Coward Robert Ford.

Still, seeing Pitt win for one of the best performances of his career is rewarding in its own right. Playing a low-key and deceptively easygoing cowboy turned stuntman, there is an ingratiating charm about Pitt’s character in Once Upon a Time… in Hollywood. It’s a charm that also masks a shockingly brutal coldness that can be turned on at the violent drop of a hat (or dog food can).

read more: How the Oscars Were Reinvented in the 21st Century

Pitt’s teaming with DiCaprio in the movie feels both like a celebration and an end of an era. Each star came to prominence in 1990s Hollywood—the same as Tarantino—which may have been the height of movie stardom cache in post-Golden Age Hollywood. In 2020, however, it is increasingly difficult imagining a movie star (or a pair of them) who can open an original movie just on the strength of their names, or that of the director’s. Yet by combining their charisma, and Tarantino’s legacy, they turned the leisurely and elegiac Once Upon a Time into one of the biggest box office hits of 2019.

That Oscar will look mighty fine sitting next to Brandy the dog’s food bowl in the future.

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David Crow is the Film Section Editor at Den of Geek. He’s also a member of both the Critics Choice Association and the Online Film Critics Society. Read more of his work here. You can follow him on Twitter @DCrowsNest.