▲Pitt was offered the lead role but turned it down, after Johnny Depp had already passed as well. It wasn't until after Edward Norton, Leonardo DiCaprio, and Ewan McGregor were all offered the role and subsequently turned it down that Christian Bale picked it up. And now his performance is legendary.

▲In one of Stephen King's greatest adapted tales, Pitt was intended for the role of Tommy Williams, but somehow he fumbled the incredible opportunity and the role went to Gil Bellows.

▲Pitt, producing the film, was originally cast as Sullivan and determined to star alongside Tom Cruise, but he dropped out. Though he continued to produce the film, his role went to Matt Damon and his costarring role went to Leonardo DiCaprio.

▲Music composer Don Davis reportedly revealed in an interview that the studio originally wanted Brad Pitt or Val Kilmer for the lead role. Could you ever see Neo as anyone other than Keanu Reeves?

▲Pitt turned down the lead role of Will, which went on to cement Hugh Grant in the hearts of audiences everywhere. Apparently Pitt thought it was too implausible that such an attractive man would need to pick up women by pretending to be a single father.

▲Pitt was considered for the role of Hephaestion, but he reportedly turned it down due to personal concerns with the character, who ended up being played by Jared Leto.

▲The role of Russell Hammond was actually written for Pitt, but he dropped out, allegedly saying, "I just don't get it enough to do it." Billy Crudup stepped in to fill his place.

▲When Pitt turned down the role of John Grady Cole in the movie adaptation of Cormac McCarthy's novel, the part went to Matt Damon.

▲Pitt really had Sophie's choice when he turned down 'Apollo 13' in order to do 'Se7en.' Both are now classics, but in retrospect it seems he made the right decision.

▲Pitt was reportedly considered for the lead role, along with Keanu Reeves and Robert Downey Jr., but the role went to William Baldwin because of how much he looked like Kurt Russell, who was playing the character's brother.

▲This one probably hurts. To make it worse, the writer originally had Pitt in mind for the part, but due to scheduling conflicts with his other movie 'Spy Game,' he dropped out, leaving ample room for Matt Damon to swoop in and take over an entire franchise.

▲Pitt had actually committed to the film, but later backed out along with director Ron Howard, for reasons that are unclear. Chris O'Donnell replaced him.

▲Pitt—along with Michael Keaton, Will Smith, and Jim Carrey—was turned down for the role of Willy Wonka, but Tim Burton probably had Depp in mind the whole time anyway.

▲Brad Pitt was considered for this American Civil War film in the role of W.P. Inman, but Jude Law ended up snagging the part alongside Nicole Kidman.

▲When Joel Schumacher was signed on to direct, Pitt was originally set to play Kevin. But, when Taylor Hackford replaced Schumacher, Pitt was out and Keanu Reeves was in, and now Reeves' name is inextricable from the sleazy defense attorney.

▲Pitt turned down the role of Rannulph Junuh in this drama about golf, and Matt Damon, once again, filled his spot.

▲Pitt was originally considered for the part of Chris "Izzy" Cole, but Mark Wahlberg got the part, costarring alongside Pitt's then-wife Jennifer Aniston.

▲Pitt was reportedly offered the lead role, but ultimately passed because he was tired of depressing stories after shooting 'Interview with the Vampire' and 'Legends of the Fall.' The role went to Bill Paxton.

▲Pitt was considered for the lead role of Inspector Fred Abberline, but Hollywood's chameleon got the role instead.

▲Pitt was reportedly considered for the role of Big Daddy, which ended up going to Nicolas Cage.

▲Pitt was reportedly set to play Turkish, but gave the role to Jason Statham in favor of the part of Mickey the "pikey" instead.

▲Pitt auditioned for the role of Private Witt in this epic war film, but the role went to a much lesser-known Jim Caviezel.

▲The actor purportedly withdrew from the mystery film because he wasn't happy with the screenplay. Russell Crowe stepped in and ended up getting the Australian Film Institute International Award for Best Actor.

▲Pitt was reportedly considered for the lead role in this crime drama, featuring stars like Sandra Bullock, Samuel L. Jackson, Kevin Spacey, and both Donald and Kiefer Sutherland, but the role went to Matthew McConaughey.

▲In the DVD commentary, Pitt reportedly states that he was originally offered a "much bigger part," but decided to take the role of the stoner Floyd instead. Christian Slater, once again, stepped in for Pitt.

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Pitt was offered the role of the lover, Paul, but turned it down, letting Olivier Martinez enjoy the spotlight.

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Pitt pulled out of Darren Aronofsky's sci-fi drama to do 'Troy,' leaving the part to Hugh Jackman.

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Pitt was reportedly considered for the role of Ichabod Crane, made famous by the revered actor-director duo of Johnny Depp and Tim Burton.

▲That's right, Leonardo DiCaprio's most iconic role lingered on the possibility of Pitt as Jack Dawson. What a different world we would be in...

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Due to scheduling conflicts, Pitt had to turn down the role of William Darcy, giving Martin Henderson the opportunity of working alongside Aishwarya Rai, one of India's most famous actresses.

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Pitt auditioned for the role of J.D., but apparently the producer and director thought he looked too sweet to play the dark character. Christian Slater, however did not.

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Brad Pitt's name first tickled the tongues of cinephiles in 1991 after appearing in 'Thelma & Louise,' and he quickly became the talk of the town in the years following. He made a name for himself with films like 'Se7en' and 'Fight Club,' but it wasn't until 2020 that he earned his first ever acting Oscar, for Best Supporting Actor in 'Once Upon a Time in Hollywood.' We all know he has the acting chops, so why did it take so long?

Perhaps his awards were lost with the roles he turned down, those might-haves and could-bes that now either comprise his biggest regrets or smartest career moves. As it turns out, Johnny Depp, Matt Damon, and Keanu Reeves’ most famous roles could have been played by him.

Check out this gallery, based on a list by Not Starring, of all the roles that Pitt could've played.