On his popular YouTube channel, Will Smith recently expressed regret for having turned down a pivotal film role in the mid-1990s. Specifically, the megastar passed on the opportunity to portray the computer programmer/hacker Neo in The Matrix; and thus, Keanu Reeves landed the gig. Smith, on the other hand, opted to commit to the role of U.S. Army Captain James T. West in Wild Wild West.

In his Storytime clip above, the Fresh Prince explains why he refused to play Neo. It was 1996, and Smith was just coming off from a steady stream of career successes including Six Degrees of Separation, the big hit Independence Day, and he was making Men in Black. He explains, “[‘The Matrix’ writer-directors] the Wachowskis, they came in, and they’d only done one movie—I think it was called ‘Bound.’ And they came in and they made a pitch for ‘The Matrix.’ And as it turns out, they’re geniuses. But there’s a fine line in a pitch meeting between genius and what I experienced in the meeting.” Indeed, Smith goes on to recount their rather odd pitch, describing the innovative “bullet time” visual effect they would soon implement in the cyberpunk flick.

Indeed, The Matrix went on to win four Academy Awards, and it was a box-office hit across the globe. And where was Smith in all of this? “So I made ‘Wild Wild West’ … I’m not proud of it,” he says. Unfortunately, the steampunk western action-comedy received disappointing reviews and profits.

Had he taken the part of Neo, The Matrix would have also differed in that Val Kilmer would have portrayed Morpheus, the part that eventually went to Laurence Fishburne. Overall, Smith reflected, “I watched Keanu’s performance—and very rarely do I say this—but I would have messed it up. I would have absolutely messed up ‘The Matrix.’” What’s his reasoning for his belief? “I wasn’t smart enough as an actor to let the movie be,” he insisted.

But not to worry; Smith went on to star in films like Ali in 2001, and The Pursuit of Happyness in 2006. And his performances in both of these films were honored with Oscar nods.

But Will Smith is hardly the only actor who skipped the chance to take on an iconic role due to confusion. Sean Connery passed on playing the long-bearded Gandalf from The Lord of the Rings. “I read the book. I read the scripts. I saw the movie. I still don’t understand it,” he admitted. And when Denzel Washington read the script for neo-noir crime thriller Se7en, he couldn’t see himself playing the murder investigator David Mills. “It was so dark and evil. Then, when I saw the movie, I was like, ‘Oh, shoot,’” he said after seeing Brad Pitt in the starring role.

Often times, scheduling conflicts are to blame, but there are many other reasons why actors decide to skip out on roles.  James Caan declined the part of R.P. McMurphy in One Flew Over the Cuckoo’s Nest, but later regretted his decision when he saw Jack Nicholson nail the performance. “I didn’t know that [Director] Milos Forman was as good as he was,” he said. And Kevin Costner wasn’t interested in The Shawshank Redemption’s character Andy Dufresne; he had better things to do—like pursue his work on Waterworld. Unfortunately, his passion project went on to be nominated for four Golden Raspberry Awards. Dufresne was played by Tim Robbins, and the film went on to be nominated for seven Academy Awards. 

And Richard Gere passed on playing Gordon Gekko in the 1987 movie Wall Street because he wasn’t sold on the part. So Michael Douglas stepped into Gekko’s shoes and went on to win an Academy Award for Best Actor. Such is the nature of the business.

Have you ever regretted passing on a role? Please share.