The two movies Woody Harrelson will always regret not making: “Oh fuck, oops!”
Once upon a time, Hollywood wasn’t sure what they were supposed to do with Woody Harrelson.
He had gotten famous for the feel-good, old-fashioned television series Cheers in the 1980s and was building an increasingly erratic filmography with movies like the Ron Shelton basketball comedy White Men Can’t Jump and Oliver Stone’s controversial serial killer caper Natural Born Killers. He had yet to stake his claim as one of the industry’s weirdest and most versatile character actors, and executives seemed hellbent on making him a leading man.
It was in this liminal space that Harrelson made what he now believes were two big fumbles, because a series of hit movies made him a go-to choice for producers, but he consistently turned them down for stranger fare, like, for example, in the late ‘90s, he chose to play legendary pornographer Larry Flynt in The People vs Larry Flynt. In retrospect, it was a genius move and earned him an Oscar nomination, but at the time, it must have looked like career suicide.
It’s hard to imagine that Harrelson, who now has three Oscar nominations to his name and is one of those actors who instantly elevates whatever movie he’s in, would have any regrets, but in a 2017 interview with Shortlist, he revealed that he has at least two.
The first was turning down the lead role in Jerry Maguire. Producer James L Brooks approached him for the role, but Harrelson told him that he didn’t think anyone would care about the life of a sports agent. “Next thing I know, I hear Tom Cruise is doing the movie, and I’m like, ‘Oh fuck. Oops!’” he recalled. The second regret was turning down Dumb & Dumber. This was an even stranger decision since he had once been roommates with one of its directors, Peter Farrelly.
“They’d had no success at that time, but really wanted me to do the movie,” he said. Ultimately, it came down to a game of pool. According to the actor, he made a bet, saying that if his former roommate won, he would star in the film, but if Harrelson won, he wouldn’t.
“The game came down to the eight ball,” he remembered, “And I’ve never been so disappointed to sink an eight ball in my life.” You’d think that if he’d wanted to be in the film as badly as he claims, he would have angled the cue a little differently, but perhaps competitiveness got the better of him. In the end, Jeff Daniels got the part, and the rest is comedy history.
Harrelson is magnanimous enough to acknowledge that he would have struggled to turn in a performance as masterful as Daniels’s, and it is hard (to the point of impossible) to imagine him playing Jerry Maguire. As with most Tom Cruise performances, it’s basically just movie star Tom Cruise that you see on screen, and he has all the swagger and raw ambition to make the character memorable. Sure, the script has plenty of standout lines, but Cruise brought a certain indelible Cruiseness to it that makes it difficult to reverse engineer with Harrelson in mind.
In the end, everyone won. Jerry Maguire was a hit, Dumb & Dumber was a hit, and Harrelson got nominated for an Oscar for Larry Flynt, and perhaps the best bit of karma, though, was that when he finally did star in a Farrelly Brothers movie (1996’s Kingpin), it flopped.
