Woody Harrelson has never been one to shy away from variety in his acting career. From big-budget blockbusters and intense crime dramas to raunchy comedies and psychological thrillers, he’s done it all. But even for a seasoned actor willing to take on almost any role, there are always the ones that slip away—the parts that, in hindsight, feel like missed opportunities. For Harrelson, one regret stands out among the rest, and the worst part? He lost it because of a game of chance that he suggested.
In 2017, while promoting War for the Planet of the Apes, Harrelson reflected on his history of turning down roles. Ironically, he had only been cast in Apes because he passed on another primate-centric blockbuster—Kong: Skull Island. While he had no real interest in Kong, he was a huge fan of the Apes franchise, so it wasn’t a decision he dwelled on. But when asked about a role he did regret passing up, he didn’t hesitate.
“Jerry Maguire,” he admitted. When legendary filmmaker James L. Brooks first pitched the idea to him, Harrelson wasn’t convinced. “Jim, I just don’t think anybody’s gonna care about an agent,” he recalled saying. When he later found out that Tom Cruise had taken the role—one that would go on to define Cruise’s career in a new way—Harrelson knew he had made a massive miscalculation.
But there was one missed opportunity that stung even more.
Back in the early ’90s, his old roommate Peter Farrelly approached him with an offer. Peter and his brother Bobby were working on a comedy and wanted Harrelson for one of the lead roles. At the time, the Farrellys had no real Hollywood success to their name, so Harrelson wasn’t exactly sold on the idea. That’s when he came up with a brilliantly terrible plan.
“Pete’s a great pool player, so I told him, ‘If I lose this game, I’ll do your movie. If I win, I’m out.’”
The game was neck and neck, coming down to the final shot. And then—clack—Harrelson sank the Eightball, sealing his fate. He wouldn’t be in the movie.
The film? Dumb and Dumber.
The Farrelly brothers’ directorial debut became one of the most successful comedies of all time, grossing $247 million and catapulting Jeff Daniels into a new realm of comedic stardom as the dimwitted Harry Dunne—the very role Harrelson had been up for. While he later admitted that Daniels was perfect for the part, Harrelson couldn’t help but feel like he had let something special slip through his fingers.
Determined not to miss out again, he made sure to sign on for the Farrellys’ next movie, Kingpin. Unfortunately, the film bombed at the box office. Then came There’s Something About Mary, another huge Farrelly hit, leaving Harrelson joking, “Mine was that little movie in the middle that nobody saw!”
A game of pool might have cost him one of the biggest comedies of the ’90s, but Harrelson’s career hardly suffered. Still, one can’t help but wonder—what if that Eightball had missed?
