Woody Harrelson’s Biggest Career Regrets: Two Roles He Passed Up
Woody Harrelson once turned down two major film roles that went on to become box office smashes. Years later, he opened up about the decisions that still make him wince.
Back in the day, Hollywood didn’t quite know what to make of Woody Harrelson. After his run on Cheers in the ‘80s, he was popping up in all sorts of films, from the basketball comedy White Men Can’t Jump to the wild ride that was Natural Born Killers. He hadn’t yet carved out his spot as one of the industry’s most unpredictable and interesting actors, and the powers that be seemed set on making him a leading man. It was during this uncertain patch that Harrelson made a couple of choices he’d later look back on with a bit of regret.
He was getting offered plenty of big projects, but often went for the oddball ones instead. Case in point: in the late ‘90s, he picked up the role of Larry Flynt in The People vs Larry Flynt. At the time, it looked like a risky move, but it ended up landing him an Oscar nod. Still, not every decision worked out so neatly.
Turning Down Blockbusters
Despite his later success, Harrelson admitted in a 2017 chat that there are two roles he still kicks himself over. The first was the lead in Jerry Maguire. Producer James L Brooks had approached him, but Harrelson wasn’t convinced anyone would care about a film centred on 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 was a spot in Dumb & Dumber. This one’s even stranger, considering he’d once shared a flat with Peter Farrelly, one of the directors.
“They’d had no success at that time, but really wanted me to do the movie,”
he said. The decision came down to a game of pool. If Farrelly won, Harrelson would take the part; 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.”
Sliding Doors and What-Ifs
It’s a bit of a head-scratcher, really. If he’d been that keen, you’d think he might have missed the shot on purpose. Maybe his competitive streak got in the way. In the end, Jeff Daniels landed the role, and the rest is comedy gold. Harrelson’s honest enough to admit he probably couldn’t have matched Daniels’s performance, and it’s tough to picture him as Jerry Maguire. Tom Cruise brought his usual energy and charm to the role, making it hard to imagine anyone else in the part.
Sure, the script had its moments, but Cruise’s presence made the character stick. Trying to picture Harrelson in that spot just doesn’t quite add up. Sometimes, things just work out the way they’re meant to.
Silver Linings and Missed Chances
In the end, everyone came out on top. Jerry Maguire was a smash, Dumb & Dumber became a classic, and Harrelson scored an Oscar nomination for playing Larry Flynt. The kicker? When he finally did team up with the Farrelly brothers for Kingpin in 1996, the film didn’t exactly set the box office alight. Funny how things turn out.