Read on to find out what surprising actors never stopped kicking themselves for giving up the chance to play a role in your favorite movies.
Marilyn Monroe
Breakfast at Tiffany’swas authorTruman Capote’s masterpiece, and his preference for the iconic, pearl-clad part of Holly Golightly was the equally iconicMarilyn Monroe. Monroe’s agent, however, advised her that playing a “prostitute” would be bad for her image, so she turned it down.
Instead, the role went toAudrey Hepburn, which became one of the characters she’s best known for. Monroe, meanwhile, madeThe Misfits, written by her husband, famous playwrightArthur Miller. The production was such a disaster that the conflicts on set about the script reportedly ended Miller and Monroe’s marriage. She would pass away the year after it was released.
John Lithgow
The Joker fromBatmanis such a great villain thatJack Nicholsonreportedly was disappointed that the part wasn’t offered to him again when directorChristopher Nolanbrought back the character inThe Dark Knight Rises(the role ended up going toHeath Ledger, who passed away shortly after filming). But Nicholson almost didn’t even get the part in the original 1989 movie.
According toJohn Lithgow, he was approached by directorTim Burtonbefore the role was offered to Nicholson, but Lithgow didn’t feel he would be right for the part. “I tried to persuade him I was not right for the part, and I succeeded,” Lithgow told Vulture about one of the first hit superhero blockbuster movies. “I didn’t realize it was such a big deal.”
Bruce Willis
Who wouldn’t want to film a sexy pottery scene with their hot wife?Bruce Willis, apparently, who passed on playing the part of the ghost inGhostafter reading the script—even though his then-wifeDemi Moorewould ultimately take the part of the ghost’s very-alive wife, Molly.
Willis shouldn’t feel bad for taking a chance on what was an admittedly strange script, however. Numerous actors passed on the film—includingTom Hanks,Tom Cruise, andKevin Bacon—beforePatrick Swayzetook on the part. It would go on to be nominated for an Oscar for Best Picture and win for Best Original Screenplay.
Leonardo DiCaprio
Leonardo DiCapriohas had one of the most enviable careers of any movie star alive. But when asked byGQin 2008 which role he turned down and wished he had taken, DiCaprio had only one reply: Dirk Diggler inBoogie Nights.The strange twist? The movie DiCaprio took instead wasTitanic.
“I think they’re both great and wish I could have done them both,” he toldGQ.But also he seemed to consider the “what ifs” if he had takenBoogie Nightsinstead ofTitanic,the movie that made him a mega-star: “It would have been a different direction, careerwise…it would have been interesting to see if I had gone the other way,” he toldGQ.
There was no star more sought-after in the early 00s thanBrad Pitt, so it’s no surprise that he was offered the role of Jason Bourne, the amnesiac action hero ofThe Bourne Identitythat launched more than a decade’s worth of sequels. Pitt had a full plate, however, and declined the role.
Instead, it went toMatt Damon,who was known mostly for his roles inGood Will HuntingandThe Talented Mr. Ripley. The part changed his career, and he went on to play Jason Bourne four more times. Pitt, meanwhile, starred in the relatively forgettableSpy Game.
Kevin Costner
In an alternate reality somewhere, when you findThe Shawshank Redemptionon TV, it’sKevin Costnerin the main role instead ofTim Robbins. Costner was offered the role before Robbins was, but he turned it down to appear in another film.
The film he made?Waterworld, far from being one of the year’sblockbuster movies.The movie was hated by critics and audiences alike, with the Associated Press reviewer writing, “Costner…is totally humorless and as dreary as the landscape he travels.”Shawshank, meanwhile, is often considered one of the best movies ever made.
Will Smith
Now they’re considered some of the most famous siblings in Hollywood, but beforeThe Matrix, theWachowskiswere basically unknowns, having directed only one movie (Bound) that hadn’t done well at the box office. So it’s hard to blameWill Smithfor saying no when they approached him about playing Neo in what became a sci-fi classic.
Unfortunately for Smith,The Matrixbecame…The Matrixand spawned two sequels, as well as video games, comic books, action figures and more—generating more than $3 billion in revenue and becoming one of the most successful franchises in history. And the movie Will Smith made instead? The universally hated bombWild Wild West.
Michelle Pfeiffer
The Silence of the Lambswas one of 1995’s most memorable movies, and Academy voters thought so too, giving the film seven nominations and five wins, includingJodie Fosterfor Best Actress in a Leading Role. The role of Clarice Starling wasn’t first offered to Foster, however.
Michelle Pfeiffer, known for her notable roles inTequila SunriseandDangerous Liaisons, was first approached to play the tenacious detective who’s able to connect with killer Hannibal Lecter. Ultimately, she turned down the Oscar-winning part because she thought the movie was too dark…though she must have changed her mind somewhere between that decision andWhat Lies Beneath.
Christina Applegate
Legally Blondeis one of the most successful comedy movies ever helmed by a woman. Spawning a sequel and at least a hundred GIFs, it’s an iconic film that helped make Reese Witherspoona household name. ButChristina Applegatewas first considered for the part.
Applegate, then known mostly forMarried…with Children, toldEntertainment Tonightin 2015 that she was afraid of being typecast as a “dumb blonde,” adding “What a stupid move that was, right?” Luckily, she had the short-lived TV showJesseto keep her busy.
Jennifer Connelly
In the late 80s and early 90s, if you were looking for an actress to play an angsty teenager,Winona Ryderwas your girl. She was played Lydia inBeetlejuice, Kim inEdward Scissorhands, and Charlotte Flax inMermaids. But none of these movies were actually aimed at teenagers themselves.
Heathers, Michael Lehmann’s 1998 schlocky, shocking cult classic, was. And although you may not be able to picture anyone but Ryder as the protagonist Veronica (ironically, one of the few main characters to not be named “Heather”), screenwriterDaniel Watersdid. Believe it or not, he originally wrote the part for actressJennifer Connelly, but she turned it down.
