The iconic comedy role Woody Harrelson regrets turning down: “I’ve never been so disappointed”

Woody Harrelson has starred in movies of all shapes and sizes throughout his illustrious career. From the most extravagant blockbusters and franchise films to crime movies, erotic thrillers and the silliest of comedies, Harrelson is willing to turn his hand to pretty much anything. However, this isn’t to say he always makes the right calls when picking roles. In truth, he has more than a few parts that he regrets turning down, but one stands out above all the others. Why? Because he lost the role thanks to a game of chance that he actually suggested playing.

In 2017, Harrelson was on the promotional trail for his latest film War for the Planet of the Apes. He spoke to Shortlist magazine about the movie, which saw him playing a terrifying military villain, and revealed that he was only able to star in it because he turned down another simian-related blockbuster. You see, he was asked about his interest in Apes only a week after saying “No, thanks” to an offer to star in Kong: Skull Island. He didn’t care at all about King Kong, but as a fan of the two previous Apes films, he was eager to play in that world.

This anecdote led the interviewer to ask Harrelson if he’d ever turned down a role and regretted it, unlike with Kong, which he was happy he’d rejected. He immediately responded, Jerry Maguire,” before admitting that he told that movie’s producer, James L Brooks, “Jim, I just don’t think anybody’s gonna care about an agent.” When he heard that Tom Cruise had accepted the part, though, he realised what a boneheaded decision he’d just made.

Interestingly, though, there was another project that Harrelson regretted turning down even more than Cruise’s Oscar-nominated sports agent romance. He revealed that he was approached by his old roommate Peter Farrelly in the early ’90s about starring in a comedy he was putting together with his brother Bobby. At that time, Harrelson claimed the brothers hadn’t experienced any success in Hollywood, but they were insistent that he consider starring in their picture. So, Harrelson made them a bet.

“Pete’s a good pool player, so I challenged him to a game,” Harrelson chuckled, “and said, ‘If I lose this game, I’ll do your movie. If I win, I’m not gonna do it.'” The game went right to the wire, with both competitors vying to pot the Eightball – and Harrelson admitted, “I’ve never been so disappointed to sink an Eightball in my life.”

The crestfallen star then watched as the Farrellys made Dumb and Dumber, a modern comedy classic that made a staggering $247million at the worldwide box office. It also gave an entirely new dimension to the career of star Jeff Daniels, who played the intelligence-deficient Harry Dunne, the part Peter wanted Harrelson to consider. Harrelson was bummed out, but he admitted, “I dunno if I could’ve played that part as well as Jeff Daniels did anyway.”

Amusingly, when the Farrellys set up their next movie, Harrelson ensured he was involved, but Kingpin unexpectedly flamed out at the box office. When they followed it up with There’s Something About Mary – an even bigger hit than Dumb and Dumber – it made an exasperated Harrelson joke, “Mine was that little movie in the middle that nobody saw!”

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