Woody Harrelson's Career Mistakes: Two Blockbusters He Passed Up
The acclaimed actor opened up about rejecting lead roles in two massive Hollywood hits that went on to define the careers of other stars, revealing the surprising reasons behind his decisions.
There was a time when Hollywood executives couldn't figure out how to use Woody Harrelson. Fresh off his breakout role in the beloved sitcom Cheers during the 1980s, the actor was building a wild and unpredictable resume. Movies like White Men Can't Jump and Natural Born Killers showed his range, but studios kept pushing him toward leading man territory.
During this uncertain period, Harrelson made what he now considers two major career blunders. Hit movies kept landing on his desk, but he consistently rejected them for more unconventional projects. Take his choice to portray controversial publisher Larry Flynt in The People vs Larry Flynt during the late '90s. The decision looked like professional suicide at the time, though it eventually earned him an Oscar nomination.
The Sports Agent Role That Got Away
Despite three Oscar nominations and a reputation for elevating every project he touches, Harrelson admits to having regrets. In a 2017 Shortlist interview, he revealed two roles he wishes he hadn't turned down. Producer James L Brooks first approached him about starring in Jerry Maguire, but Harrelson dismissed the concept entirely.
He told Brooks that audiences wouldn't care about a sports agent's story. "Next thing I know, I hear Tom Cruise is doing the movie, and I'm like, 'Oh fuck. Oops!'" Harrelson recalled. The film became a cultural phenomenon and cemented Cruise's status as a Hollywood heavyweight.
A Pool Game That Changed Comedy History
His second regret involved Dumb & Dumber, which made the rejection even more bizarre since he'd been roommates with director Peter Farrelly. The Farrelly Brothers hadn't achieved success yet but desperately wanted Harrelson for the lead role. Instead of simply saying no, he proposed settling the matter with a game of pool.
The bet was simple: if Farrelly won, Harrelson would star in the movie. If Harrelson won, 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." Jeff Daniels eventually landed the part, creating one of comedy's most memorable performances.
Why Everything Worked Out
Looking back, it's nearly impossible to imagine Harrelson in either role. Tom Cruise brought his signature swagger and ambition to Jerry Maguire, qualities that made the character unforgettable. The script had great lines, but Cruise's star power gave it that special something that's hard to replicate.
Everyone came out ahead in the end. Both Jerry Maguire and Dumb & Dumber became massive hits, while Harrelson scored his Oscar nomination for Larry Flynt. The best twist of fate? When he finally did work with the Farrelly Brothers on Kingpin in 1996, the movie flopped completely.