Woody Harrelson’s Missed Chances: Two Roles He’ll Never Forget
Woody Harrelson once passed on two major film roles that went on to become box office sensations. Discover which iconic parts he turned down—and why he still remembers those decisions.
There was a period in the 1990s when Woody Harrelson’s career seemed to be at a crossroads. Having made his name as the affable barman in Cheers, he was still searching for his place in the world of cinema. His choices were unpredictable—one moment starring in a basketball comedy, the next in a controversial crime drama. Hollywood, meanwhile, appeared uncertain about how to cast him, often nudging him towards leading roles that didn’t quite fit the mould.
Amidst this uncertainty, Harrelson found himself repeatedly declining offers for high-profile projects. Instead, he gravitated towards more unconventional scripts, such as taking on the role of Larry Flynt, the infamous publisher, in a biopic that would later earn him an Academy Award nomination. At the time, though, it must have seemed a rather risky move, bordering on professional self-sabotage.
Regrets and What Might Have Been
Despite his later success and critical acclaim, Harrelson has admitted that there are a couple of decisions he’d rather not have made. In a candid moment, he confessed to having passed up the chance to play the lead in Jerry Maguire. The offer came from James L Brooks, but Harrelson was unconvinced by the premise.
“Next thing I know, I hear Tom Cruise is doing the movie, and I’m like, ‘Oh fuck. Oops!’”
he recalled, with a wry sense of regret.
Another opportunity slipped through his fingers in even stranger fashion. Harrelson was approached for Dumb & Dumber, a film that would go on to become a comedy classic. The twist? He’d once shared a flat with Peter Farrelly, one of the directors. The decision, as it turned out, hinged on a game of pool.
“They’d had no success at that time, but really wanted me to do the movie,”
he said. The wager was simple: if Farrelly won, Harrelson would take the part; if not, he’d walk away.
“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.”
Sliding Doors and Silver Linings
It’s tempting to wonder how things might have played out had Harrelson taken a different shot. He admits that, in hindsight, he might have let his competitive streak get the better of him. The role eventually went to Jeff Daniels, whose performance is now considered iconic. Harrelson, for his part, is gracious enough to acknowledge that he may not have matched Daniels’s comedic timing.
As for Jerry Maguire, it’s nearly impossible to picture anyone but Tom Cruise in the role. The film’s success owed much to Cruise’s particular brand of charisma, and Harrelson himself seems to recognise that. The script may have been sharp, but Cruise’s presence made it unforgettable.
Paths Not Taken
In the end, the films Harrelson turned down became massive hits, while his own career took a different, but no less interesting, trajectory. He received an Oscar nod for his portrayal of Larry Flynt, and, in a twist of fate, when he finally did appear in a Farrelly Brothers film—Kingpin—it failed to make much of a splash at the box office.
Looking back, Harrelson’s choices may have seemed questionable at the time, but they helped shape a career that’s anything but ordinary. And while he may still wince at the memory of that fateful pool game, it’s clear he’s found his own way to stand out in Hollywood’s crowded landscape.