How Many Oscars Does Brad Pitt Have? Not Nearly Enough.

Photo: VALERIE MACON/AFP/Getty Images.
As of February 9, 2020, Brad Pitt is now an Oscar winner for his acting. He finally won, after seven nominations, for his performance in Quentin Tarantino's Once Upon a Time in ... Hollywood.
In his speech, he dedicated his win to his director, his friend and co-star Leonardo DiCaprio, his stuntmen, and his kids. He did not joke about being single.
Pitt has two Oscars; he previously won an award for producing in 2012.
Original story follows.
Brad Pitt is many things: actor, producer, father, and sculptor. One thing he is not: an Academy Award winner. At least, not for acting. Pitt does have one Oscar, which he received in 2012 as a producer of Best Picture winner 12 Years A Slave. While one Oscar isn’t worth more than any other, it feels like an incredible snub that the 56-year-old Oklahoma native has been attending the award show religiously for the past 20 years and never won an award for the way he chews, the way he goofs, or the way he schemed in Ocean's Eleven (and Twelve, and Thirteen)
Remember how much the internet rallied behind Leonardo DiCaprio to finally take home that little gold man in 2016? It’s time to do the same for Pitt as he enters his well-earned Hollywood Pitt-aissance.
This year, Pitt is nominated for Best Supporting Acting for playing Cliff Booth in Quentin Tarantino’s Once Upon a Time... in Hollywood, the director’s ode to Hollywood’s past, and his (questionable) rewriting of Sharon Tate’s future. Pitt's portrayal of the semi-retired stuntman, who spends his time chauffeuring around his best friend Rick Dalton (DiCaprio) — “closer than a brother and a little less than a wife” — and stripping down to his Levis, has swept awards season so far. The actor has won a Golden Globe, a BAFTA, Critics’ Choice, and SAG awards, to name a few, for bringing to life one half of 2019’s best bromance. It seems pretty inevitable that he’ll once again take the stage on February 9, deliver a rousing speech, mocking himself and others. If so, this will mark his first Oscar win for acting. 
Pitt’s actual first Oscar, however, represents an arguably much more significant contribution to the Hollywood canon. 
It all goes back to Plan B, the production company he founded in November 2001 with Jennifer Aniston, his wife at the time, and Brad Grey. In 2005, after Pitt and Aniston divorced and Grey left the business, Pitt became the sole owner. Since then, three of Pitt the Producer’s films (The Departed, 12 Years a Slave, and Moonlight) have won Best Picture. (Pitt was only named as a main producer on 12 Years a Slave, hence the one Oscar — the politics of the Academy are complicated.)
Photo: Moviestore Collection/Shutterstock.
Brad Pitt in Ocean's Eleven, one of his most iconic roles.
Moonlight’s (well-deserved) surprise win for Best Picture at the 2017 Oscars felt like a turning point for the award show, and the acting world at large. By helming films that put a spotlight on new, diverse, and complicated stories, Pitt is using his celebrity power to uplift meaningful voices and projects. That means less time acting for himself, and for the accolades that go along with that, and more time producing for others. 
“As I get older and transition does its thing, the great thing about producing is you still get to be part of what I love most, which is storytelling,” Pitt told Entertainment Weekly last year, while promoting his film Ad Astra (a phenomenal movie about loneliness, which he should have been nominated as Best Actor for, but I digress). “Or maybe it’s just me, maybe I’ve just seen my interests broadening or shifting into other things. But no. No!...It’s not a claim of retirement.” 
But, since this whole story is about this Sagittarius man of the moment (a Sag man is one who, according to, “forever in pursuit of truth and knowledge, and he deeply desires a career that supports his passion for freedom as well as his penchant for bold undertaking”; his typical model is “easy come, easy go.”), let’s revisit all the nominations that he lost.
In 1996 he lost Best Supporting Actor for 12 Monkeys to Kevin Spacey in The Usual Suspects. In 2009 and 2012 he lost Best Actor to Heath Ledger’s posthumous Joker win and Jean Dujardin for The Artist, respectively. In 2014 he won as a producer for 12 Years A Slave (which he also starred in), and in 2016 he lost as a producer for The Big Short (in which he starred with Jeremy Strong — consider this a request for a Pitt Succession cameo), up for Best Picture.
So, that’s a total of seven Oscar nods, one win for producing, and zero for his dancing in Burn After Reading.
The idea of hearing another wild speech from Pitt should be reason alone for the Academy to vote for his on-screen performance. I wonder if he’ll cry when he wins.
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