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Brad Pitt’s career is like an open invitation to a star-studded dinner party where every seat is filled with iconic roles, juicy scripts, and unforgettable performances. One minute, he’s the charming, smooth-talking con artist inOcean’s Eleven, the next, he’s the tortured soul with an existential crisis inFight Club, and inTroy, he’s not just conquering the Colosseum, but stealing hearts like a true Hollywood gladiator.
He has dipped his toes into every genre, from heart-pounding thrillers to intimate dramas, and made each role feel like a tailor-made suit.
Even the brightest stars, it seems, need to take a pause now and then, casting a reflective gaze upon the roads they didn’t take. In fact, Pitt’s career is also laced with “What If?”moments—those iconic roles he could’ve had but walked away from. And who knows? Had he stepped into those shoes, we might have been calling him the legendary one we never saw coming.
Let’s take a stroll through the aisles of opportunity and look at the roles Brad Pitt passed on….and even wished he hadn’t.
5.Apollo 13
Imagine this:Brad Pitt, notKevin Bacon, orbiting through space withTom Hanks. Sounds like a solid deal, right? Well, that almost happened. When the 1995 filmApollo 13—directed by Ron Howard—was casting for the role of Jack Swigert, Pitt was initially considered. However, the actor passed up the opportunity to star inSe7en, the chilling thriller directed by David Fincher.
However, Pitt’s mother wasn’t exactly thrilled by his decision. As he shared withThe Morning Call(viaFar Out Magazine):
I was talking to my mom the other night, and she said, ‘I just saw the best movie called Apollo 13.’ I said, ‘Mom, I turned that down for Seven and wait until you see the movie.’
While his mother was upset, Pitt was confident thatSe7enwas the right choice, even if it meant losing out on a space epic. Meanwhile, critics would later singApollo 13‘s praises, withRotten Tomatoesgiving the film a stellar 96% approval rating, and it went on to win two Academy Awards.
4.The Matrix
Ah,The Matrix. If there’s one role that cementedKeanu Reeves’ legacy, it’s Neo. But it could have easily been Brad Pitt in that iconic leather trench coat. Well, his decision to pass onThe Matrixis perhaps one of the most talked-about ‘what ifs’ in Hollywood. In an interview at the 2019 Santa Barbara International Film Festival (viaPeople), Pitt confirmed what many suspected—he was offered the iconic role of Neo.
He described his choice to decline the part, saying,
I’ll give you one, only one, because I really believe it was never mine. It’s not mine. It’s someone else’s and they go and make it. I really do believe in that. I really do. But I did pass on the Matrix. I took the red pill.
Pitt went on to play Tyler Durden inFight Club—a role that has since becomeone of his most defining performances. In retrospect, it’s hard to imagine anyone else but Reeves embodying Neo, and perhaps Pitt was right when he said the role was never really his to take.
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WhenThe Matrixhit theaters in 1999, it revolutionized the science fiction genre, grossingover $460 millionon a $63 million budget and earning critical acclaim with an 83% score onRotten Tomatoes. But would it have worked with anyone other than Reeves? Probably not.
3.Almost Famous
In Cameron Crowe’s semi-autobiographical 2000 filmAlmost Famous, Billy Crudup stole the show as Russell Hammond, the charismatic lead guitarist of a ’70s-era rock band. However, before Crudup landed the role, it was actually Brad Pitt who was in the running to play the rock star.
According to Crowe, the director had a strong connection with Pitt after their collaboration onSay Anythinga decade earlier (viaOriginspodcast). The role of Russell Hammond and complicated relationship with the film’s leading lady, Penny Lane, seemed like it could be a perfect fit for Pitt. However, during the casting process, the actor ultimately passed on the role. Crowe explained on theOrigins Podcastthat
He [Pitt] had fallen in love with the idea of the character.
But he ultimately didn’t feel like there was enough substance on the page. Additionally, Crowe suggested that Pitt might have been “uncomfortable” with the age difference between Hammond and Penny Lane (played byKate Hudson), given that Penny is a teenager in the film.
Despite the film’s underwhelming theatrical release,Almost Famoushas since been embraced as a cult classic. The film went on to receive four Academy Award nominations, including Best Original Screenplay, and won a Golden Globe for Best Motion Picture—Musical or Comedy. OnRotten Tomatoes, the film boasts an impressive 91% approval rating.
While Pitt missed out on a memorable role, Crudup’s performance became one of the defining moments of the film.
2.The Departed
This is another missed opportunity that might have had fans wondering what could have been. WhenThe Departedwas in its early stages, Brad Pitt was slated to play Colin Sullivan, the corrupt cop played by Matt Damon in the final cut. However, as soon asMartin Scorsesegot involved, Pitt backed out, feeling he was “too old”for the role of a young officer fresh out of the academy.
In a 2007 interview withInterview Magazine, Pitt explained his decision:
I thought it would be better if [the leads] were younger guys that were just starting their lives… I thought I was too old for it.
But wait…Pitt still played a significant part in the film’s success as a producer.
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The Departedwent on to become a massive hit, grossing over $290 million (Box Office Mojo) and winning four Academy Awards, including Best Director for Scorsese and Best Adapted Screenplay for William Monahan. While Pitt didn’t take home an Oscar for this one, it’s hard to argue with the success of the project, which is universally considered a modern crime classic.
1.The Shawshank Redemption
Perhaps one of the most regrettable roles Brad Pitt turned down was that of Tommy Williams inThe Shawshank Redemption, which is now widely regarded as one of the greatest films ever made. The film, based on a Stephen King novella, tells the story of Andy Dufresne (played byTim Robbins) and his years in prison, alongside his friend Ellis Redding (Morgan Freeman).
Initially, Pitt was set to play Tommy Williams, a young and naive inmate whose brief involvement in the story adds crucial twists to the narrative. However, as his star began to rise, Pitt dropped out in favor ofInterview with the Vampire, where he starred oppositeTom Cruise. According to an interview for the 25th anniversary ofThe Shawshank Redemption, Pitt confessed (viaUSA Today):
I just believe in the way things work out, and that was someone else’s role.
That“someone else” turned out to be Gil Bellows, whose portrayal of Tommy was well received. Despite the film’s rocky start at the box office,The Shawshank Redemptioneventually found its audience and is now considered one of the greatest films of all time, holding an 89% approval rating onRotten Tomatoes.
Well, Brad Pitt has had a career full of hit movies, but the roles he turned down—whether by timing, instincts, or personal decisions—have helped shape his legacy in ways we’ll never fully know. Maybe the ones he let slip away weren’t meant for him, or maybe, just maybe, the universe had bigger plans. Either way, with a career as diverse and successful as his, it’s hard to say he has any regrets!
Siddhika Prajapati
Senior Journalist & Content Head
Articles Published :3310
With over 3,300 articles carved into the digital walls of FandomWire, Siddhika Prajapati excels at creating, curating, and elevating engaging stories. She takes pride in giving these stories a home and, of course, she’s got a Google Knowledge Panel to prove it!Whether it’s reviewing the latest drop on Netflix, Amazon Prime, or Apple TV+, or analyzing the cultural echoes of a streaming hit on Paramount+ or Max, Siddhika is always writing three steps ahead of the discourse.
