Once Upon a Time...in Hollywood...Brad Pitt was almost the star of these massive movies. 

After a career filled with iconic performances, Pitt, 56, finally took home his first-ever acting Oscar at the 2020 Oscars on Sunday night, winning Best Supporting Actor for his celebrated turn as Cliff Booth in Quentin Tarantino's Once Upon a Time...in Hollywood

The film marked the first time Pitt and Leonardo DiCaprio, one of Hollywood's other most celebrated leading men, worked together, an on-screen collaboration that excited industry insiders and fans alike. But the two actually came this close to starring in a hit film over a decade ago before Pitt ultimately decided to drop out, believing he was "too old" for the role. Yes, really. 

But it wasn't the only time Pitt has almost starred in an iconic role that ultimately ended up going to another actor, as the superstar could've been the face of not one but two major action movie franchises in an alternate universe. 

The person who definitely benefited from Pitt's decisions not to star in certain movies? One of his Ocean's 11 co-stars, who ended up snagging two massive roles, including one that launched a billion dollar franchise.

Here are seven iconic roles Pitt almost played...

Brad Pitt, Keanu Reeves, The Matrix, Iconic roles Brad Pitt almost played

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Brad Pitt, Billy Crudup, Almost Famous, Iconic roles Brad Pitt almost played

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Brad Pitt, Gil Bellows, The Shawshank Redemption, Iconic roles Brad Pitt almost played

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Brad Pitt, Matt Damon, The Bourne Identity, Iconic roles Brad Pitt almost played

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Brad Pitt, Matt Damon, The Departed, Iconic roles Brad Pitt almost played

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Brad Pitt, Christian Bale, American Psycho, Iconic roles Brad Pitt almost played

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Brad Pitt, Christian Slater, Heathers, Iconic roles Brad Pitt almost played

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