It’s a well-known piece of film trivia that Will Smith turned down The Matrix. It’s up there on the list of other famous almost-casts: Molly Ringwald could have been in Pretty Woman, Eric Stoltz was Marty McFly for a few weeks of filming.

But Smith missing out on the role of Neo in The Matrix always seemed especially tragic considering he turned it down to star in the biggest bomb of his early career, Wild Wild West. “I’m not proud of it,” Smith said of the Western comedy in the latest entry of his YouTube “Storytime” series. In addition to the Wild Wild West apology, Smith goes into detail about why he turned down The Matrix, and why he’s ultimately happy he did.

Why Will Smith Turned Down The Matrix

It was 1998, and Will Smith was at the top of his game. He was in the middle of a critical and commercial hot streak following Bad Boys, Independence Day, and Men in Black. “However I threw the ball, it was going in,” Smith recounted. But as the saying goes, the higher the climb, the harder the fall — and Smith fell hard. It was a misstep that he, and everyone else, can trace back to The Matrix pitch meeting, in which the Wachowskis attempted to sell the biggest blockbuster star on their high concept movie. As you could guess, things did not go so well. Smith says:

“So after we made Men in Black, the Wachowskis, they came in and they had only done one movie. I think that movie was called Bound. And they came in and 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.”

Smith puts on a colorful reenactment of the Wachowskis’ pitch, turning his baseball cap backwards and putting on a frat bro voice to describe a painfully bad pitch — one in which the Wachowskis tried to describe the film’s now-iconic freeze frame jump, only to make it sound like, “Imagine if you could stop jumping in the middle of the jump. But then people could see around you 360 while you’re jumping and…when you stop jumping.”

Unimpressed, Smith went on to do Wild Wild West, and Keanu Reeves took the role of Neo in The Matrix, which went on to become a seminal sci-fi classic. But while Smith has some regrets, he thinks it was all for the best considering how perfect Reeves and Laurence Fishburne were in their roles.

“If I had done it because I’m black, then Morpheus wouldn’t have been black ’cause they were looking at Val Kilmer. So, I probably would have messed The Matrix up, I would have ruined it. I did y’all a favor,” he concludes.

Thanks, Will.