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Though so many huge stars have had a few slip-ups when it comes to choosing roles, as even the best actors working today have features in box office bombs or critical failures, Brad Pitt has seemingly managed to skate through his career barely ever tripping up.

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However, that isn’t to say that he hasn’t let a lot of great roles slip through his hands, as there are as many roles that he has turned down as there are iconic characters in his filmography.

10 Heathers (1989)

Though Pitt is one of the biggest movie stars on the planet, in the late 1980s, he was just another struggling actor trying to get by. In 1988, Pitt auditioned for Christian Slater’s role in the cult classic, Heathers, as the screenwriter Daniel Waters has explained to Yahoo Entertainment. The reason that Pitt never got the role of J.D. was simply that the actor just didn’t stand out.

9 The Matrix (1999)

As reported by The Independent, Brad Pitt revealed that he turned down the lead role in one of the most revolutionary movies ever made, The Matrix. When discussing that he turned down the role, he hilariously referenced the movie by saying that he “took the red pill.” Though The Matrix features one of the best fight scenes of the 90s, Pit did go on to star in a movie in 1999 that featured just as great (but entirely different) fight scenes in Fight Club.

8 The Departed (2006)

It was Brad Pitt who owned the rights to The Departed, the remake of the Hong Kong movie Infernal Affairs, and he envisioned starring in the movie alongside DiCaprio too, according to an interview the actor gave with Interview. Pitt had planned to play Sullivan but eventually decided that the role should go to a younger actor.

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Pitt then even considered playing Dignam, who has the most quotable line of the whole movie, but that ended up going to Mark Wahlberg, who ended up getting nominated for an Academy Award for the role.

7 Waking Up In Reno (2002)

First reported by Variety way back in 1999, Pitt was set to star alongside his wife at the time, Jennifer Anniston, in the romantic comedy. The two eventually dropped out just before filming and they were replaced by Billy Bob Thornton and Charlize Theron. However, it seems like Pitt made the right decision to drop out of the road trip movie, as it ended up being one of Charlize Theron’s worst movies.

6 State Of Play (2009)

Back in 2009, Cinema Blend reported that Russell Crowe replaced Brad Pitt in the movie State of Play, a crime drama co-starring Ben Affleck. Pitt left the project because he didn’t think the script was good enough. State of Play isn’t the only movie Russell Crowe has replaced Pitt in, as the actor was set to star in Ridley Scott’s American Gangster, one of the best movies directed by Scott. However, Pitt has gone on to work with Scott on more than one occasion, as he featured in Thelma and Louise and The Counselor.

5 Sleepy Hollow (1999)

As reported in 1998 by Entertainment Weekly, Pitt was in the running to star in Tim Burton’s Sleepy Hollow, one of the fairytale movies too scary for kids. The actor was reportedly offered the role, but unsurprisingly, Depp was always the director’s first choice to play the wimpish hero Ichabod Crane, and it was paramount who urged Burton to consider casting Pitt.

4 Crimson Tide (1995)

According to Mental Floss, Pitt was at one point attached to the classic Tony Scott action movie. Al Pacino was attached to play Captain Ramsey in Crimson Tide, but once the Heat actor backed out, so did Pitt. It was a good job that Pitt didn’t star in the movie, as Crimson Tide marked the first of six collaborations between Tony Scott and Denzel Washington, sparking a great working relationship that includes Man On Fire and Deja Vu.

3 Deadpool 2 (2018)

With the hype surrounding the follow-up to one of the most successful R-rated movies of all time, there were news stories about casting almost every day.

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One of the most exciting updates, coming from Collider, was that Brad Pitt was in talks to play Cable in Deadpool 2, though it was later reported it wasn’t possible due to scheduling restrictions. However, Pitt still had an amazing blink-and-you’ll-miss-it cameo in the movie as the superhero Vanisher.

2 Charlie And The Chocolate Factory (2005)

According to Stars Insider, Pitt was on course to play Willy Wonka in Tim Burton’s remake of Charlie and the Chocolate Factory. It’s hard to imagine Pitt completely letting his hair down and acting as loose as Johnny Depp does in the movie, but maybe that’s a good thing, as Depp’s performance is one of the reasons the movie was ridiculed by critics. But there are actually some fans who believe Johnny Depp’s portrayal might be the best.

1 Kick-Ass (2010)

According to CBR, Kick-Ass director Matthew Vaughan originally wanted Pitt for the role of Big Daddy, but the shooting schedule conflicted with Quentin Tarantino’s revisionist war movie, Inglourious Basterds. However, everything works out in the end as Nicholas Cage was eventually cast in the role, and he put his strange stylistic twist on the character, and Inglourious Basterds is arguably the best Tarantino movie.

NEXT: Brad Pitt: 5 Reasons Cliff Booth Is His Best Character (& 5 Why It’s Still Tyler Durden)

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