It is a well-acknowledged fact that Brad Pitt is the frontrunner this award season, courtesy his role as Cliff Booth in Once Upon a Timeâ¦in Hollywood. This marks Brad's seventh Oscar nomination. And while recently he won the Best Picture for 12 Years Of Slave, he's never actually won an individual acting Oscar.
It's strange he wasn't even nominated for iconic roles in films like Fight Club or Se7en! One can draw parallels to Leonardo DiCaprioâs Oscarless-phase which was filled with memes on the internet before his triumphant win for The Revenant in 2016. It is funny how films like The Curious Case Of The Benjamin Button too weren't enough to get him an Academy nod. So here's a list of Pitt's nominations over the years that could've won him an Oscar but didn't and also the only time he won an Oscar for the team effort.

Nomination 1: Best Supporting Actor (1996), 12 Monkeys

Brad Pitt scored his very first nomination for 12 Monkeys for playing Jeffrey Goines in Terry Gilliamâs sci-fi thriller. At the time he was already popular and a household name, courtesy iconic films like Se7en, Legends of the Fall and lastly Thelma and Louise. He lost the award to Kevin Spacey, who worked on The Usual Suspects that year. 

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Nomination 2: Best Actor (2009), The Curious Case of Benjamin Button

The second nomination for Pitt came after a considerable time gap. Benjamin Button (an Oscar nomination after a 13-year gap for Pitt), his character ages in reverse, from a shrivelled, seemingly aged baby to an adorable infant by the end of the film as he ages in reverse. He lost to Sean Penn, who starred in Milk that year.

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Nominations 3 and 4: Best Actor and Best Picture (2012), Moneyball

Brad Pitt's next nomination at the Oscars was in the film, Moneyball (as Oakland Aâs manager Billy Beane) based on the book by Michael Lewis. Unfortunately, he lost to Jean Dujardin for The Artist and the same film took Best Picture as well. 

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Nomination 5: Best Picture (2014), 12 Years a Slave

Finally, 2014 was a lucky year for Brad. He was able to hold his very own (yet shared) gold statuette for 12 Years a Slave (a period drama in which he has only a small part as a Canadian laborer who is anti-slavery), a film he also produced, had won Best Picture that year.  

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Nomination 6: Best Picture (2016), The Big Short

In The Big Short, Brad Pitt plays the character of Ben Rickert, a retired securities trader, and a sage crash predictor. The film is a deep dive into the 2008 housing bubble that led to the terrible global recession the same year. Unfortunately, he couldn't win the Acadamy Award a 6th time in a row despite his brilliant performance in the film.  The film lost to Spotlight that year.  

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Nomination 7: Best Supporting Actor (2020), Once Upon a Time...in Hollywood

At 56, Brad Pitt may have given his best performance yet in the film, Once Upon a Time...in Hollywood. This role deserves an Oscar, but he's also up against a list of talented and deserving actors likeâTom Hanks, Anthony Hopkins, Al Pacino, and Joe Pesci.

While we're rooting for Pitt and hope he finally makes it to the other side and he probably will, at the end of the day it's great to see how the statuette acknowledgment has never deterred his impeccable performances over the years. 

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