Why hasn't Brad Pitt won an acting Oscar yet?

2019 has been a pretty great year for Brad Pitt - the actor.

The 55-year-old has not only impressed in Quentin Tarantino’s Once Upon a Time in Hollywood as an ageing hunk of a stuntman called Cliff Booth but his performance as an astronaut on a mission to find his father, in this week’s new release Ad Astra, has garnered rave reviews too.

After a two year gap from appearing on-screen - his last performance was in the Netflix movie War Machine - Pitt’s return proves that he’s still got the acting chops so it’s no wonder there has been a lot of chatter about him getting nominations for an Oscar, both in the Best Actor (Ad Astra) and Supporting Actor (OUATIH) categories.

Surprisingly, he’s never actually won an Academy Award in the acting categories despite being nominated three times.

He was first up for a gong in 1996, for his supporting role in the sci-fi thriller Twelve Monkeys.

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“[The film is] fused by Brad Pitt’s performance as Jeffrey Goines, a jabbering psychotic who may just be more dangerous than he looks,” wrote Owen Gleiberman for Entertainment Weekly at the time.

“Pitt does a hammy, bug-eyed turn, but his manic reaction time and rabid, get-a-load-of-me deviousness work for the character, and for the film’s central mystery.”

As gripping as his performance might have been, Pitt was up against James Cromwell (Babe), Ed Harris (Apollo 13), Tim Roth (Rob Roy) and Kevin Spacey whose winning turn in The Usual Suspects was hard to compete with.

His next opportunity to take home a gold statue for acting came in 2009 with his lead performance in The Curious Case of Benjamin Button, which earned a staggering 13 nominations in total.

The film was mostly praised with Kirk Honeycutt of The Hollywood Reporter calling it "superbly made and winningly acted by Brad Pitt in his most impressive outing to date," though some were unconvinced like Kimberley Jones of the Austin Chronicle, who said "Fincher's selling us cheekboned movie stars frolicking in bedsheets and calling it a great love. I didn't buy it for a second."

The film ended up winning three awards but not for Pitt personally, who lost out to Sean Penn who won for his role as gay rights activist Harvey Milk in Milk.

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Biopics do notoriously well at the Academy Awards and 2009 was no different and three years later, Pitt would get his last acting Oscar nomination for starring in one himself.

Both he and his co-star Jonah Hill were nominated for Best Actor and Supporting Actor for their respective turns as Billy Beane and Peter Brand in the 2011 Moneyball.

The sports flick was inspired by Michael Lewis's 2003 nonfiction book of the same name, which told the story of Oakland Athletics’ 2002 baseball season and their general manager Beane's attempts to assemble a competitive team on a budget by using Brand's sabermetric approach to scouting and analysing players.

“Brad Pitt is at the top of his own game as Beane,” wrote David Elliot in his San Diego Reader review. “Cocky and often nonchalant, he is gnawed by doubts that he tries to cover by grabbing a snack or pitching a grin.”

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The 84th Academy Awards really should have been Pitt's year with his main competitor being George Clooney for his stunning performance in The Descendants. However, the Academy voters proved once again how much in love with themselves and Hollywood they really are by awarding Jean Dujardin the Best Actor award for The Artist.

Pitt hasn’t been nominated for an acting Oscar since though he has picked up a few Best Picture nods as a producer and even won one too. Moneyball and The Big Short (2016) were both produced through his Plan B production company though it was in 2013, with 12 Years A Slave, that he was finally allowed to take a gold statue home.

The Steve McQueen-directed movie was nominated in nine categories and as well as winning Best Picture it saw Lupita Nyong’o and John Ridley win for Best Supporting Actress and Best Adapted Screenplay, respectively.

Pitt had a small role in the film based on the life of Solomon Northup (Chiwetel Ejiofor), a free black man from upstate New York who was kidnapped and sold into slavery in the South, though the win as a producer marked a move away from the limelight into a more supportive behind-the-scenes role.

Plan B Entertainment has helped produce several Oscar-winning movies in the time since, including Selma, Moonlight, Beautiful Boy, If Beale Street Could Talk and Vice and Pitt has simultaneously taken a step back from acting, which he spoke about during a recent interview with The New York Times.

“It’ll be fewer and farther in between for me, just because I have other things I want to do now,” Pitt said. “When you feel like you’ve finally got your arms around something, then it’s time to go get your arms around something else.”

This new attitude may have contributed to his decision to not actively campaign this Oscar season if he does get nominated for either or both of his 2019 performances.

“Oh, man. I’m gonna abstain,” he told Entertainment Weekly.

“I mean, you never know, and it’s really nice when your number comes up,” he added. “But the goal is for the film to land, to speak to someone whether it’s now or a decade from now. I find chasing it is actually a disservice to the purity of your telling a story and a shackling thing to focus on.”

I guess we’ll have to wait until Sunday, 9 February 2020, when the Oscar nominations are announced to see if he changes his tune.

Ad Astra is in cinemas now.