If you’re sitting there trying to remember the name of that one flick where Woody Harrelson plays a grumpy mentor or a terrifyingly smooth villain, join the club. The guy is everywhere. Honestly, he’s one of the few actors who successfully jumped from "sitcom bartender" to "prestige movie star" without losing his soul—or his hair, mostly.
Most people know him as Woody Boyd from Cheers, but his filmography is a wild, decades-long ride. From the gritty 90s cult classics to the massive blockbusters of the 2020s, Woody’s range is basically unparalleled. He’s been a basketball hustler, a serial killer, a drunken mentor in a dystopian future, and even a symbiote-hosting psychopath.
The Breakout Years: Hoops and Killers
Woody didn't just walk into Hollywood. He sprinted. After years of being the lovable, slightly dim-witted bartender on Cheers, he needed a "vibe shift." He found it on the blacktop.
In 1992, he teamed up with Wesley Snipes for White Men Can't Jump. It was a massive hit. You've probably seen it on cable a thousand times, and it still holds up because Woody actually has game. But if that movie established him as a leading man, his next big swing turned him into a lightning rod for controversy.
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We're talking about Natural Born Killers (1994). Directed by Oliver Stone, this movie was—and is—pure chaos. Harrelson played Mickey Knox, a role so far removed from his Cheers persona that it basically shattered his "nice guy" image forever. It was violent, experimental, and brilliant.
A few other 90s gems you might've forgotten:
- Indecent Proposal (1993): He’s the husband who lets Robert Redford sleep with his wife for a million dollars. Awkward.
- Kingpin (1996): This is arguably his best comedy. He plays Roy Munson, a washed-up bowler with a rubber hand. It’s the Farrelly brothers at their peak.
- The People vs. Larry Flynt (1996): This earned him his first Oscar nomination. He played the real-life Hustler magazine founder, and he was incredible.
The Blockbuster Era: Hunger Games and Beyond
Fast forward a bit. Woody didn't just fade away like most 80s stars. He pivoted into being the "secret weapon" for big franchises.
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If you ask a teenager today what movies did Woody Harrelson play in, they aren't going to say Kingpin. They’re going to say The Hunger Games. As Haymitch Abernathy, he brought a much-needed soul (and a lot of booze) to a franchise that could have been just another YA adaptation. He appeared in all four films from 2012 to 2015, becoming the face of the "reluctant mentor" trope.
He also joined the Star Wars universe in Solo: A Star Wars Story (2018) as Tobias Beckett. Was the movie perfect? Maybe not. Was Woody great in it? Always. Then there's the Now You See Me series. He plays Merritt McKinney, a world-class mentalist. It’s a role that lets him lean into his natural charisma and mischief.
The Recent Hits and 2026 Releases
Woody is currently having a massive moment. He just wrapped up Now You See Me: Now You Don't (the third one in the series), which is hitting home video in early 2026. He's also been busy with:
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- Triangle of Sadness (2022): He plays a Marxist yacht captain. It’s hilarious and weird.
- Champions (2023): A heartfelt sports comedy where he coaches a team of players with intellectual disabilities.
- Venom: Let There Be Carnage (2021): He went full-tilt as Cletus Kasady/Carnage.
The Awards Bait: When He Gets Serious
While he loves a good paycheck as much as anyone, Woody is a heavy hitter when it comes to prestige drama. You've likely seen him in No Country for Old Men (2007) as the doomed Carson Wells. Short role, huge impact.
His performance in The Messenger (2009) is often cited by critics as his best work. He plays a casualty notification officer, and it’s gut-wrenching. It got him another Oscar nod. Then came Three Billboards Outside Ebbing, Missouri (2017). His portrayal of Sheriff Willoughby was so nuanced that it almost stole the movie from Frances McDormand.
What's Next for Woody?
As of 2026, Woody isn't slowing down. He’s moved back to Texas, lobbying for film incentives and staying busy. Look out for Full Phil, where he plays a wealthy industrialist trying to reconnect with his daughter (played by Kristen Stewart).
The takeaway for fans: If you're looking to marathon his best stuff, start with Natural Born Killers for the shock, move to Kingpin for the laughs, and finish with The Messenger for the acting masterclass. You'll see why the industry still can't get enough of him.
To truly appreciate his range, try watching an episode of Cheers and then immediately follow it up with his role in True Detective. The fact that it's the same guy is honestly kind of a miracle.