Brad Pittis a decorated actor and film producer who is undeniably one of Hollywood’s most popular and celebrated movie stars. His career has spanned nearly 35 years and during that dazzling period, the performer has starred in iconic movies likeFight Club, 12 Monkeys, SevenandThe Ocean’s 11trilogy(among countless others). Pitt has won numerous accolades including two Oscars, an Emmy Award, and two Golden Globes, and his place in the entertainment business remains unparalleled.

Renowned for playing characters like Tyler Durden, Benjamin Button, and Louis de Pointe du Lac, it’s safe to say Pitt has dominated every part he’s given. But even movie stars of his caliber have suffered career setbacks, either passing on memorable roles or simply being rejected for them. Let’s dive into some of the biggest roles Brad Pitt didn’t get or turned down.

A scene from Charlie and the Chocolate Factory

Charlie and the Chocolate Factory (Didn’t Get)

Brad Pitt was a serious contender to take on the iconic role of the eccentric Willy Wonka in the 2005adaptation of the Roald Dahl classicfrom Tim Burton,Charlie and the Chocolate Factory, going up against a slew of other major actors vying for the role including Bill Murray, Michael Jackson, Jim Carrey, Michael Keaton, and of course Johnny Depp.

Pitt’s production company Plan B Entertainment helped finance the picture, and the actor auditioned for the lead role but was ultimately turned down in favor of Depp, Burton’s longtime collaborator. Though the studio was excited at the prospect of Pitt to star, Burton knew all along that Depp was the only actor he wanted in the role.

Damon Bourne Supremacy 2004 Universal

Jason Bourne (Turned Down)

Matt Damon became a certified action superstar when he took on the thrilling role of formerCIA assassin Jason Bourne, but the face of the franchise could have looked a lot different if Brad Pitt had accepted the part. The Hollywood heavy hitter was the first actor considered to play Bourne, and he was even directly offered the role byThe Bourne Identitydirector Doug Liman. However, Pitt had scheduling conflicts due to his commitment to Tony’s Scott’sSpy Gameand was forced to pass on the film. Pitt starred alongside Robert Redford in the fellow action thriller, while Damon went on to lead the successful series in four installments.

Neo in The Matrix (Turned Down)

Touted as one of thegreatest sci-fi films of all time, the Wachowskis' critically-acclaimed blockbusterThe Matrixfamously features Keanu Reeves as cybercriminal and expert computer hacker Neo, with the beloved actor sharing the screen with Laurence Fishburne and Carrie-Anne Moss. Though it is now well-known that Will Smith passed on the part, Pitt was another major A-list actor whose name was in the running to headline the groundbreaking flick.

Whenboth he and Val Kilmerturned down Neo, the studio went with Reeves, who impressed the filmmakers with his innate understanding of the concept and subject matter. Pitt officially confirmed turning down the role whenhe joked about the decisionin 2021, having admitted, “I did pass onThe Matrix.I took the red pill. That’s the only one I’m naming… I wasn’t offered two or three. Only the first, just to clarify that.”

Keanu Reeves stopping bullets in The Matrix

Jack Dawson in Titanic (Didn’t Get)

Director James Cameron’sepic romance disaster masterpieceTitanicskyrocketed sensational leads Leonardo DiCaprio and Kate Winslet to superstardom and became the first film to reach the billion dollar mark at the box office. Fans across the world fell head-over-heels for DiCaprio’s charming third-class passenger Jack Dawson, who against all odds develops a passionate romance with the high-class Rose DeWitt Bukater on the doomed ocean liner.

Related:Titanic 25 Years Later: A Masterpiece or a Disasterpiece?

Leonardo DiCaprio and Kate Winslet in Titanic

BeforeDiCaprio nabbed the coveted role, Cameron was eyeing many of Hollywood’s finest leading men including Tom Cruise, Matthew McConaughey, Johnny Depp and of course Pitt himself. The legendary director felt the actors were too old to play the part of a 20-year-old, and it went to DiCaprio instead;Titanicwent on to win 11 Academy Awards and has grossed over $2.2 billion at the box office.

Patrick Bateman in American Psycho (Didn’t Get)

Christian Bale delivered a tour de force performance as the demented investment banker-turned serial killer Patrick Bateman in the 2000 horror hitAmerican Psycho, leaving audiences in awe atBale’s ability to transform on screen.Based on the Bret Easton Ellis novel of the same name, the film initially had both Pitt and director David Cronenberg attached in the ’90s, but that version was eventually scrapped due to creative differences between the pair. Surprisingly, Cronenbergdidn’t want to shoot the violence, and after cycling through various directors and stars the project found its movie magic in Bale and filmmaker Mary Harron.

Russell Hammond in Almost Famous (Turned Down)

Cameron Crowe’s Oscar-winning dramedyAlmost Famousfeatures a star-studded cast of cinema greats including Frances McDormand, Kate Hudson, Billy Crudup, and Philip Seymour Hoffman, and follows 15-year-old child prodigy William as he shadows the sensational band Stillwater. Crudup portrays frontman Russell Hammond in his breakthrough performance, but the character was almost portrayed by Brad Pitt. The actor spent months preparing for the role with Crowe, but during the process Pitt felt the character wasn’t the right fit for him.

Crowe would later speculatewhy theFight Clubstar turned down the role, saying, “I wept. I knew that [Brad Pitt] had never fully fallen in love with the character. He had fallen in love with the idea of the character. But maybe there just wasn’t enough on the page. He told me [money] wasn’t the case. I think it was probably half-and-half. I think he was also uncomfortable with the age difference between Russell and Penny Lane.”

Christian Bale wields an ax in American Psycho

Jim Swigert in Apollo 13 (Turned Down)

For his breathtaking depiction of America’s failed 1970 mission to the moon, Ron Howard enlisted the talent of Tom Hanks, Kevin Bacon and Bill Paxton to bring the thrilling real story to life on the big screen. Bacon appears as command module pilot Jack Swigert inApollo 13, one of three astronauts who embark on the lunar mission only for it to be aborted after an oxygen tank failed. Brat Pitt was offered the part of Swigert but rejected the part in favor of starring in David Fincher’s crime thrillerSeven.

Hehilariously relayed the decisiononThe Morning Callin 1995, saying, “I was talking to my mom the other night, and she said, ‘I just saw the best movie, calledApollo 13.She said, ‘You have to do more movies like this!’ I said, ‘Mom, I turnedApollo 13down forSe7en! Wait until you see that movie!’”

J.D. in Heathers (Didn’t Get)

In Daniel Waters' beloved 1989 black comedyHeathers,a cruel high school clique becomes the target of a rebellious outsider hellbent on murdering the mean girls one by one; when he begins to terrorize innocent students, his girlfriend and fellow clique member Veronica (Winona Ryder) must put an end to the violence. Brad Pitt was one of many up-and-comers to audition for the role of the deranged J.D., and while he did a decent job the part went to Christian Slater.

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Waters described Pitt at the timeas a “good-looking guy with a laconic drawl," but he didn’t really fit the vibe of the edgy character. After trying out, Pitt told the director, “Hey man, I know I’m not anybody, but for what it’s worth, that’s brilliant.” Though he was passed over for the role, Pitt’s career didn’t stay down for very long.

Colin Sullivan in The Departed (Turned Down)

With some of Hollywood’s finest performers teaming up withrevered director Martin Scorsesefor his epic crime thrillerThe Departed, it’s not surprising that the gritty picture dominated both the box office and awards season. Chronicling the Boston underground crime world and Irish mob as they are secretly infiltrated by the police, the distinguished picture stars Matt Damon as mob spy Colin Sullivan, who is groomed by crime boss Frank Costello (Jack Nicholson) to gain intel. Pitt was offered the part of the career criminal when Leonardo DiCaprio was set to co-star, but he ultimatelypassed on playing Sullivan, believing a younger actor should play the role; Pitt instead decided to produce the thriller.