Once Upon a Time in Hollywood also marked Brad Pitt and Leonardo DiCaprio’s first on-screen appearance together. The two could have featured together earlier but Brad turned down the role because he felt he was “too old” for it.
Following are the films Brad almost starred in:
1. The Matrix
Brad Pitt recently admitted at the Santa Barbara International Film Festival. "I did pass on The Matrix. I took the red pill. That's the only one I'm naming…I wasn't offered two or three. Only the first one, just to clarify that."
2. Almost Famous
Pitt worked with Crowe for months before leaving the project. Crowe told AL.com in 2014. "His head was still in Fight Club and the part was a little underwritten. It was the most underwritten in the script, and he couldn't trust it enough. I've talked to him since. I love the guy. I think he's hilarious, and I thought he would have been funny in the movie. If I had waited a few more months, he might have come around to it, but we had to get going. But Billy Crudup worked out great."
3. The Shawshank Redemption
Pitt decided to star in Interview With the Vampire instead. He told the publication he had no regrets.
"It would have been kind of cool to be in, but I'm not a regret guy in that way. I just believe in the way things work out, and that was someone else's role. Even the feeling of, 'Ooh, that would've been nice' would redirect a choice later down the road. So it all works in tandem in that way."
4. The Bourne Identity
Matt Damon took up the lead role as spy Jason Bourne in The Bourne Identity after Pitt became unavailable. He committed to Spy Game instead.
5. The Departed
This was the film in which Leo and Pitt were bound to feature together. Pitt had bought the rights to remake Hong Kong hit Internal Affairs, which became The Departed. Pitt was cast to play Sullivan. But the star dropped out, saying a younger actor should play the part—"I thought I was too old for it," he told Interview\
6. American Psycho
Christian Bale took on the role of Patrick Batemen. But an earlier version of the film directed by David Cronenberg chose to star Pitt before creative differences hindered the project.
Pitt did not audition for the part. But there is a tape of Pitt reading the role of J.D., at a table-read of Heathers ahead of its release in 1988. He read it to help his friend Stacey Travis who did not have anybody to read the part of J.D. with her.