13 A-Listers Who Turned Down Iconic Roles (and Still Regret It)

ENTERTAINMENT
By Sophie Carter

Hollywood is full of what-ifs and could-have-beens. Sometimes, even the biggest stars pass on roles that end up becoming legendary. Whether they doubted the script, had scheduling conflicts, or simply misjudged the potential, these decisions haunt them to this day. Here are some of the most famous actors who said no to parts that would have changed cinema history.

1. Will Smith – Neo in The Matrix

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Picture this: Will Smith dodging bullets in slow motion instead of Keanu Reeves. Smith was actually the first choice for Neo in The Matrix, but he turned it down to star in Wild Wild West instead. That western flop became one of his biggest career missteps.

Smith has openly admitted in interviews that he didn’t understand the concept when the Wachowskis pitched it to him. The special effects and philosophical storyline seemed too risky at the time. He now calls it one of his greatest professional regrets.

The Matrix went on to earn over $460 million worldwide and became a cultural phenomenon that defined a generation of sci-fi filmmaking.

2. Sean Connery – Gandalf in Lord of the Rings

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The legendary James Bond actor was offered the role of Gandalf and a reported $450 million payday if he accepted profit-sharing. Connery passed because he admitted he didn’t understand the script. That’s right—he turned down nearly half a billion dollars!

Director Peter Jackson personally approached Connery multiple times, but the Scottish actor remained unconvinced. He later said he read the books and still didn’t get it. The role went to Ian McKellen, who became inseparable from the character.

After seeing the trilogy’s massive success, Connery confessed he regretted the decision and acknowledged he should have trusted Jackson’s vision despite his confusion.

3. Emily Blunt – Black Widow in Iron Man 2

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Before Scarlett Johansson became synonymous with Black Widow, Emily Blunt was Marvel’s top choice. Unfortunately, contractual obligations forced her to star in Gulliver’s Travels instead. Talk about bad timing!

Blunt has spoken about how devastated she was to miss out on joining the Marvel Cinematic Universe. The scheduling conflict left her heartbroken, especially watching the franchise explode into the biggest movie series ever. She would have been part of over a decade of blockbuster films.

Johansson’s Black Widow became one of the most beloved Marvel characters, appearing in nine films and earning her own standalone movie in 2021.

4. Tom Selleck – Indiana Jones in Raiders of the Lost Ark

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That iconic fedora and whip almost belonged to Tom Selleck! He was Steven Spielberg’s first choice for Indiana Jones, but CBS wouldn’t release him from his Magnum P.I. contract. Selleck was forced to watch Harrison Ford make the role legendary.

The actor has said it remains his biggest career disappointment. While Magnum P.I. was successful, it never reached the cultural impact of Indiana Jones. Selleck even did a screen test in the full costume, and photos show he looked perfect for the part.

Harrison Ford’s portrayal became so iconic that it’s now impossible to imagine anyone else cracking that whip through ancient temples and Nazi hideouts.

5. Gwyneth Paltrow – Rose in Titanic

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Can you imagine someone other than Kate Winslet shouting “I’m flying!” on that ship’s bow? Gwyneth Paltrow was heavily considered for Rose and even met with James Cameron. She ultimately decided against it, calling the shooting schedule too demanding.

Paltrow later admitted she wonders what would have happened if she’d accepted. Titanic became the highest-grossing film of all time and won eleven Academy Awards. The role turned Winslet into a global superstar overnight.

Though Paltrow won an Oscar for Shakespeare in Love the following year, she’s acknowledged that Titanic’s cultural impact was something entirely different and unprecedented in cinema history.

6. Matthew Broderick – Walter White in Breaking Bad

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Ferris Bueller as a meth-cooking chemistry teacher? It almost happened! Matthew Broderick was approached for Walter White before Bryan Cranston auditioned. Broderick turned it down, reportedly uncomfortable with the dark subject matter.

The role required an actor willing to transform from sympathetic teacher to ruthless criminal. Broderick preferred lighter material and couldn’t see himself in such a morally complex character. His loss became Cranston’s career-defining triumph.

Breaking Bad is now considered one of the greatest TV shows ever made. Cranston won four Emmy Awards for the role, and Walter White became one of television’s most unforgettable antiheroes in entertainment history.

7. John Travolta – Forrest Gump

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Life is like a box of chocolates, and John Travolta picked the wrong one. He was offered Forrest Gump but chose to make Pulp Fiction instead. While Pulp Fiction revived his career, he still wonders about the road not taken.

Travolta has said in interviews that turning down Forrest Gump haunts him. Tom Hanks won an Academy Award for the role, and the film earned over $678 million worldwide. It became one of the most quoted and beloved movies of the 1990s.

Interestingly, Travolta’s career did benefit from Pulp Fiction, but Forrest Gump’s heartwarming story touched audiences in ways few films ever have, creating an enduring legacy.

8. Al Pacino – Han Solo in Star Wars

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“May the Force be with you,” said in Al Pacino’s distinctive voice? George Lucas wanted exactly that! Pacino was offered Han Solo but found the script too confusing. He’s admitted he didn’t understand what Star Wars was supposed to be about.

The Godfather star later said he regrets not trusting Lucas’s vision. Harrison Ford took the role and became one of Hollywood’s biggest stars. Han Solo became a cultural icon, spawning countless merchandise and even a standalone film decades later.

Pacino’s career flourished anyway, but he’s acknowledged missing the chance to be part of one of the most successful franchises in movie history was a significant mistake.

9. Molly Ringwald – Vivian in Pretty Woman

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The Breakfast Club star was director Garry Marshall’s first choice for the role of Vivian Ward. Ringwald turned it down because she felt uncomfortable with the prostitution storyline. She wanted to move away from her teen image but not quite that dramatically.

Julia Roberts stepped in and delivered a star-making performance that earned her an Oscar nomination. Pretty Woman became one of the highest-grossing romantic comedies ever, making over $460 million worldwide. Roberts became America’s sweetheart overnight.

Ringwald has since said she respects her younger self’s decision but acknowledges it would have completely changed her career trajectory and kept her in the Hollywood spotlight much longer.

10. Michelle Pfeiffer – Clarice Starling in Silence of the Lambs

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Before Jodie Foster became forever linked with FBI trainee Clarice Starling, Michelle Pfeiffer was offered the role. She passed because the script’s violence and disturbing content made her too uncomfortable. The material was darker than anything she’d done before.

Foster took the role and won her second Academy Award. The film swept the major Oscar categories and became a thriller masterpiece. Hannibal Lecter and Clarice’s psychological dance became one of cinema’s most memorable dynamics.

Pfeiffer later admitted she made a mistake and should have pushed through her discomfort. The role would have showcased her dramatic range in ways her previous romantic and action roles hadn’t allowed.

11. Denzel Washington – Detective Mills in Se7en

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What’s in the box? Denzel Washington almost found out! He was director David Fincher’s original choice for Detective Mills but declined because of the dark, nihilistic ending. Washington preferred roles with more hopeful messages and moral clarity.

Brad Pitt accepted instead and delivered one of his most intense performances. The film’s shocking finale became legendary in thriller cinema. Se7en earned critical acclaim and has influenced countless crime movies since its 1995 release.

Washington has hinted in interviews that he occasionally regrets choosing to avoid darker material early in his career. The role would have shown audiences a grittier side of his acting abilities.

12. Hugh Jackman – James Bond in Casino Royale

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007 with Wolverine’s intensity? Almost! Hugh Jackman was approached to play James Bond in Casino Royale but felt the commitment would be too overwhelming. He was already locked into the X-Men franchise and didn’t want to juggle two massive action series simultaneously.

Daniel Craig took the role and redefined Bond for a new generation. Casino Royale became the highest-grossing Bond film at the time and revitalized the franchise. Craig’s grittier, more emotional Bond won over critics and audiences alike.

Jackman has said he doesn’t regret the decision since Wolverine kept him plenty busy, but he admits playing Bond would have been an incredible honor and career highlight.

13. Christina Applegate – Elle Woods in Legally Blonde

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Bend and snap! Christina Applegate was originally cast as Elle Woods but had to drop out due to scheduling conflicts. She was devastated to leave the project, knowing the script was something special and could be a huge hit.

Reese Witherspoon stepped in and made Elle Woods an iconic feminist character. Legally Blonde earned over $140 million worldwide and spawned sequels, a musical, and countless Halloween costumes. Witherspoon’s bubbly yet determined portrayal became a cultural touchstone.

Applegate has been gracious about missing out, praising Witherspoon’s performance. However, she’s admitted it stings watching what could have been one of her signature roles belong to someone else forever.