Without a doubt, Brad Pitt is one of the biggest movie stars in the world. He is a versatile and compelling actor who has built an amazing career filled with memorable roles in some projects that have become classics. Of course, like an actor at his level, there are some famous roles he almost played.

Whether these were early roles he auditioned for and didn’t get, or roles he was offered but decided to turn down, Pitt’s list of films he almost starred in is almost as impressive as his actual filmography. While it would have been fun to see him in some of these lost roles, there are others we’re glad he missed out on.

10 Should Have Done: Tommy – The Shawshank Redemption (1994)

Based on a Stephen King story, The Shawshank Redemption is a prison drama about a man serving a life sentence in the titular prison. Late in the film, a young criminal named Tommy is brought to the prison and quickly becomes friends with the main character while also revealing a significant secret.

Pitt was on the brink of stardom when he was offered the role of Tommy, but he passed on it. While this didn’t delay his rise to fame, Pitt could have been very memorable and sympathetic as the young prisoner.

9 Glad He Didn’t: Turkish – The Bourne Identity (2002)

Pitt is the kind of rare actor who has achieved incredible success while largely avoiding the franchise movies. However, he was in mind for one stellar action series when the role of badass super-spy Jason Bourne was written for him.

Pitt can certainly handle the action hero roles, but this part feels better suited for his friend Matt Damon. At the time, Damon had never played the action hero and the atypical role for him made the character more interesting.

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8 Should Have Done: Will – About A Boy (2002)

About a Boy is a charming romantic comedy that starred Hugh Grant as Will, a single slacker who forms a bond with a young boy who he uses to pose as a single father in order to meet women.

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Pitt was close to taking on the role of Will but turned it down because he found the premise to unbelievable. Though Grant was fantastic in the movie, this is a very different role than we’ve ever seen Pitt play and it could have been a lot of fun. He still hasn’t done a real romantic comedy and this would have been a great one to start with.

7 Glad He Didn’t: Russell – Almost Famous (2000)

Cameron Crowe’s love of 70s rock music helped to create the wonderful, charming, and entertaining comedy Almost Famous which is set in that world. It follows a young rock journalist who follows an up-and-coming band around on their tour.

Crowe had met with Pitt about playing the band’s lead guitarist, Russell Hammond. Pitt was reportedly excited about the part but just wasn’t in love with the material and was nervous about the age gap in the romance with Kate Hudson’s character. In the end, Billy Crudup was the right choice as Pitt’s stardom would have overshadowed the more reserved part.

6 Should Have Done: Colin – The Departed

Martin Scorsese finally won an Oscar for his gangster film The Departed. The film tells the story of a cop who goes undercover with the mob as he is hunted by a mob member who infiltrates the police department.

The initial idea was for Pitt and Tom Cruise to play the two roles. Pitt, who was a producer, decided it would work better with younger actors, so Leonardo DiCaprio and Matt Damon were chosen. But seeing Pitt and Cruise face off in a Scorsese crime film would have been amazing.

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5 Glad He Didn’t: Clarence – True Romance

One of Pitt’s most hilarious roles is his small cameo in the wild crime film True Romance. In that film, he plays a stoner named Floyd who is an unknowing participant in the climactic mob shootout.

However, before taking that role, Pitt was offered the lead role of Clarence, eventually played by Christian Slater. Pitt didn’t find the character relatable, so he passed on the part. Slater ended up balancing the awkward and cool aspects of the character wonderfully and Pitt was freed up to play Floyd.

4 Should Have Done: Big Daddy- Kick-Ass

Pitt is one of the few actors who has avoided high-profile superhero roles. That might be why he seemed like a fun choice to play Big Daddy in Kick-Ass, a movie that very much played against the expectations of the superhero genre.

Big Daddy was a former police officer turned brutal vigilante who trained his young daughter as his equally brutal sidekick. Nicolas Cage had a lot of fun in the role, but it would have been a blast to see Pitt dressed up in that Batman-esque costume to take on the bad guys.

3 Glad He Didn’t: Leonard – Memento

Christopher Nolan first grabbed people’s attention with his captivating and inventive crime film Memento. The film followed Leonard, a man who suffers from short-term memory loss who leaves clues for himself to find his wife’s killer.

Pitt was close to signing on to the film in the lead role but ended up turning down the role. As a result, Nolan went with a lesser-known actor, Guy Pearce, in order to keep the budget manageable which worked in the film’s favor.

2 Should Have Done: Cable – Deadpool 2

Just like with True Romance, Deadpool 2 was a movie in which Pitt ended up with a cameo role after turning down a much larger part. While his brief part as The Vanisher was hilarious, Pitt was first offered the role of the time-traveling assassin Cable.

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Josh Brolin did a good job with the role, which he admits was not a fun role to play. But it would have been great to see Pitt in a big-budget and silly comic book movie as well as see him go toe-to-toe with Ryan Reynolds.

1 Glad He Didn’t: Neo – The Matrix

One of the most influential movies of the 1990s, The Matrix is an innovative and spell-binding sci-fi action epic. The movie follows a man named Neo who is taken out of his mundane life when he is exposed to the truth that his world is a simulation run by machines.

Pitt turned down the role of Neo which then went to Keanu Reeves. Despite Pitt’s obvious acting skills, Reeves was the perfect man for the role. It is hard to imagine Pitt as this aimless man freed from a mundane life which Reeves pulls off quite well.

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