Brad Pitt Passed on These Iconic Matt Damon Characters

Back in 1986, a 22-year-old Brad Pitt sat down with Tiger Beat and shared a glimpse of his dreams for the future. At the time, he imagined that by 32 he would be married with kids, but he also had clear ideas about his career.

Pitt wanted to be respected as an actor and to one day start his own production company. He told the magazine that Kevin Costner’s career was a major inspiration. By the mid-1990s, Pitt had already surpassed many of those early goals.

He starred in a string of films that were both commercial hits and critically praised. True to his ambition, he co-founded Plan B Entertainment in 2001. The company quickly became a powerhouse, producing Oscar-winning films like 12 Years a Slave and Moonlight.

Even with such a successful career, Pitt has occasionally reflected on the roles he passed on—parts that helped define other actors’ careers, including Matt Damon’s. One of the biggest missed opportunities was the role of Jason Bourne in the 2002 thriller The Bourne Identity.

Pitt had been the first choice and was interested in the part, but he couldn’t take it because he was already committed to Tony Scott’s Spy Game. Another major “what if” moment came with Martin Scorsese’s The Departed.

Pitt and his Plan B partner Brad Grey had bought the rights to remake the Hong Kong thriller Internal Affairs, intending for Pitt to play the undercover officer Colin Sullivan. But Pitt felt he had aged out of the character’s motivation.

In a 2007 interview, he explained, “I felt the story worked better with younger guys who were just starting their lives.” That decision opened the door for Damon, who delivered one of the decade’s most acclaimed performances.

Even though Pitt passed on a few defining roles, his career continues to thrive. He is currently filming The Riders in Hydra, Greece, a psychological drama directed by Edward Berger. In the film, Pitt plays a father searching across Europe for his missing wife, starring alongside Julianne Nicholson and Danny Huston.

2025 was also a major year for him. He led the racing epic F1, directed by Joseph Kosinski, playing retired driver Sonny Hayes, mentoring a rookie played by Damson Idris. The film was a critical success and earned four Academy Award nominations, including Best Picture.

Fans can also look forward to The Adventures of Cliff Booth later this year. The film, which draws inspiration from Once Upon a Time in Hollywood, was directed by David Fincher and written by Quentin Tarantino. Production wrapped in January, and it’s set for a major Netflix release.

From nearly playing Jason Bourne to passing on The Departed, Pitt has reached the respected actor status he dreamed about at 22. With multiple projects in the works and a legacy already cemented, he continues to balance blockbuster action, intense drama, and thoughtful collaborations, proving that some “what ifs” don’t define a career—they just make it more interesting.

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