Hollywood isn’t just about red carpets, award speeches, and blockbuster premieres—it’s also a world of “what ifs.” For every career-defining role, there’s a story of an actor who said no, missed out, or misjudged a script, and the regret sometimes lasts a lifetime. From billion-dollar flops to iconic hits they passed on, these are the 10 biggest actor regrets in Hollywood history. We’re counting down in reverse order, keeping the suspense alive.
10. Uma Thurman – The Lord of the Rings
Imagine Uma Thurman wielding a sword as Eowyn, riding forth across Middle-earth. Nearly did. Thurman was cast but had just given birth to her first child and wasn’t up to the demanding New Zealand shoot. She would later confess that it was “one of the worst decisions ever made” and admit that she missed out on becoming part of what became a film phenomenon. Miranda Otto filled in, made Eowyn indelible, and Thurman’s remorse became Hollywood legend.
9. Madonna – Catwoman and The Matrix
Before her pop dominance, Madonna had a taste of some big-time movie offers. She turned down Catwoman in Batman Returns and Nomi Malone in Showgirls, but her actual sadness? Passing on The Matrix. Madonna has since declared it “one of the greatest films ever,” and fans can only wonder at how a very different Neo—or in this instance, a very different film universe—might have been. Michelle Pfeiffer and Carrie-Anne Moss landed the parts, and Madonna’s “What If?” continues to be the stuff of legend.
8. Arnold Schwarzenegger – The Rock
Action star Arnold Schwarzenegger was offered the opportunity to appear in The Rock, a part that ultimately went to Nicolas Cage. When given a dirty, scrawled script by producer Jerry Bruckheimer, Schwarzenegger returned it, telling them to come back when it was refined. By the time it had been cleaned up, Cage had signed on. Schwarzenegger went on to regret turning it down, defending Cage’s work but wishing he himself had leapt in.
7. Leonardo DiCaprio – Boogie Nights
Prior to Titanic launching him into superstardom, Boogie Nights came along with a starring role offered to DiCaprio. He turned it down for Jack Dawson instead, but afterwards conceded, “Boogie Nights is a movie I loved and wish I’d done.” Mark Wahlberg stole the role and made it happen, and though Titanic catapulted DiCaprio into fame, fans can’t help but speculate on how things might have gone differently.
6. Emily Blunt – Black Widow
Emily Blunt was initially offered Black Widow in Iron Man 2, but conflicting scheduling with Gulliver’s Travels prevented her from joining the MCU. She referred to it as “a bit of a heartbreaker,” admitting the billion-dollar windfall she lost. Scarlett Johansson played the part and became a household name, although Blunt did end up working with Robert Downey Jr. on Oppenheimer, mellowing out the hurt somewhat.
5. Halle Berry – Speed
Before Sandra Bullock boarded that speed bus, Halle Berry got the opportunity to play Annie Porter in Speed. She declined the role, laughing that in her film, “the bus didn’t leave the parking lot.” Berry later regretted it, as Bullock made the movie an action classic. Berry found her action stride eventually in John Wick: Chapter 3, but Speed is one of her biggest misopportunities.
4. Burt Reynolds – James Bond
Burt Reynolds was offered James Bond in Diamonds Are Forever, but declined, thinking, “An American can’t play Bond—it has to be an Englishman.” Years later, he called it “stupidity.” Sean Connery returned to the role, cementing the classic Bond legacy, while Reynolds’ own suave potential remained a tantalizing “what could have been.”
3. Matt Damon – Avatar
Matt Damon had a golden chance: the star of James Cameron’s Avatar, plus a 10% share of the box office. He turned it down to remain with the Bourne franchise. Given that Avatar went on to gross more than $2.7 billion, Damon afterwards conceded that it was “the dumbest thing an actor ever did in the history of acting.” Sam Worthington took over, and Damon’s missed paycheck entered Hollywood lore.
2. Denzel Washington – Seven
Denzel Washington passed on Brad Pitt’s part in Seven, believing the script was “too demonic.” Seeing the completed film, he admitted, “Oh man, I blew it.” Although his rationale was sound, Seven became a thriller cult classic, and Pitt’s starring performance left audiences wondering what Denzel could have done with the creepy character.
1. Will Smith – The Matrix
The all-time Hollywood regret? Will Smith’s refusal to play Neo in The Matrix. Smith hadn’t fully understood the Wachowskis’ presentation and took Wild Wild West instead—a miserably failed venture. Afterwards, he confessed, “And then I saw The Matrix, and I was like, you jump and you freeze! That was the right pitch!” Keanu Reeves solidified his place in film history, and Smith’s lost chance is among the most legendary “what ifs” in Hollywood.
Hollywood is a land of alternate universes. Picture Madonna as Catwoman, Matt Damon as lue Na’vi, or Denzel Washington uttering, “What’s in the box?” Each regret is a tale, each pass is speculation, and each missed chance contributes to the mythos of Tinseltown. Sometimes what you don’t do is as interesting as what you do.