20Money Train
Harrelson and Wesley Snipes were a bankable duo after White Men Can’t Jump, and even though this 1995 collaboration hasn’t stood the test of time, it’s still a fun watch. The mile-a-minute action-comedy sees Harrelson and Snipes playing foster brothers Charlie and John, who work as New York City transit cops. To pay off his gambling debts, Charlie cooks up a scheme to rob a train that transports subway revenue.
19Now You See Me
Yeah, the Robbing Magicians Movie was good, silly fun! It’s no Ocean’s Eleven, but Harrelson and his costars Jesse Eisenberg, Isla Fischer, and Dave Franco have surprisingly strong chemistry as a crew of illusionists called the Four Horsemen—who begin robbing banks in public during their tours, which promptly confounds the FBI.
18Game Change
Harrelson inhabited political strategist Steve Schmidt in this HBO satire of 2008’s McCain/Palin presidential campaign. He rounded off the ensemble nicely, even if Julianne Moore stole the show with her performance as Sarah Palin.
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17Zombieland: Double Tap
Zombieland: Double Tap isn’t as stellar as the original, but you’ll have tons of fun seeing Harrelson back in the saddle as Tallahassee. In this film, he lives in the White House with the previous movie’s crew as zombies mutate into new, more powerful forms.
16Venom: Let There Be Carnage
Harrelson is excellent as the serial killer Cletus Kasady, who is infected with a symbiote called Carnage—just as he is being executed. Plus, the actor has great chemistry with Tom Hardy as Eddie Brock/Venom.
15The Highwaymen
Harrelson can seamlessly play both criminals and the law. He pairs very well with Kevin Costner in this period piece, in which they star as two former Texas Rangers who are asked to track down the notorious criminals Bonnie and Clyde. Even if they’re not quite Marty and Rust, The Highwaymen is still an exciting watch.
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14A Scanner Darkly
In this Richard Linklater–directed Philip K. Dick adaptation, Harrelson plays a roommate of Keanu Reeves’s main character, undercover agent Bob Arctor. He spends most of his time hanging out on their couch doing a psychedelic drug (called Substance D) and having rambling conversations.
13Kingpin
Harrelson has starred in some great sports comedies through the years—and this Farrelly Brothers–directed bowling pic is perfectly silly in the best way. He plays a former bowling prodigy who, after losing his hand, coaches a young Amish player in order to go pro and defeat the rival who betrayed him.
12Triangle of Sadness
As an alcoholic superyacht captain in Ruben Östlund’s class satire—who goes down with his ship while debating communism and quoting people smarter than him!—Harrelson is the film’s highlight.
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11The Hunger Games
Harrelson grows with the character of Haymitch throughout the Hunger Games series. He starts off as a cynical, booze-swigging former Games winner but turns into a canny mentor and ally to Katniss and company as they mount a revolution against President Snow.
10Seven Psychopaths
Playing an intimidating dude in a film chock-full of murderers and psychopaths, Harrelson is a wild card as gangster Charlie Costello, who hounds the main characters after they steal his beloved shih- tzu, Bonny, for reward money.
9The Thin Red Line
Terrence Malick’s war epic is exciting, harrowing, and yet another example of Harrelson doing a lot with little screen time. He plays Sergeant Brian Keck—and has a devastating scene that we won’t spoil, just in case you haven’t seen the film.
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8The Edge of Seventeen
Harrelson has an aptitude for playing put-upon and apathetic characters while remaining charismatic as heck. He uses that talent to its full extent in the coming-of-age comedy The Edge of Seventeen. As history teacher Mr. Bruner, he reluctantly mentors awkward student Nadine Franklin, who is played by Hailee Steinfeld (in a career-best performance, by the way).
7Three Billboards Outside Ebbing, Missouri
Harrelson earned his third Academy Award nomination for playing Police Chief Bill Willoughby in Martin McDonagh’s crime drama. He may have lost out to costar Sam Rockwell in the Best Supporting Actor race, but he delivers just as important of a performance in this blistering watch.
6The People vs. Larry Flynt
Of course, Harrelson has a biopic on his résumé, too, and it’s directed by Miloś Forman, the filmmaker behind Amadeus and One Flew Over the Cuckoo’s Nest. The actor shines in the title role, fully committing to the fictionalization of the controversial Hustler publisher Larry Flynt’s life. The film depicts his rise to riches, frequent run-ins with the law, and conflicts with the anti-pornography movement.
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5Natural Born Killers
Natural Born Killers is a surreal nineties gem that holds up today as a whip-smart satire, with some stellar action scenes to boot. Harrelson and Juliette Lewis play a pair of psychopathic killers whose romance, mass-murder sprees, and subsequent imprisonments are covered feverishly by news channels, turning them into celebrities. If you’re okay with a challenging and gritty watch, this underrated Oliver Stone film is a solid movie-night pick.
4No Country for Old Men
In a movie loaded with powerhouse performances, Harrelson nails the role of Carson Wells—a veteran and hitman who ends up in the crosshairs of the terrifying rival contract killer Anton Chigurh. Even with just a couple short scenes in this sprawling crime drama—which is adapted from the Cormac McCarthy novel of the same name—Harrelson still left his mark.
3White Men Can’t Jump
Harrelson and Wesley Snipes are an incredible duo in this vibrant sports comedy. The former plays hotheaded streetballer Billy Hoyle, a scam artist who hustles money by encouraging people—who assume he has no skills, since he’s white—to bet against him. His rivalry and partnership with Snipes’s character, Sidney Deane, (still!) makes the movie a blast to watch, as they cook up streetball scams while continuing to roast and challenge each other.
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2The Messenger
If you want a compelling war drama without any combat, The Messenger follows two casualty notification officers for the U.S. Army. Harrelson is Captain Tony Stone—the strict mentor of new officer Will Montgomery (Ben Foster). The film is an understated and sometimes dark character study that shows how the losses of war affect soldiers and their loved ones at home. Harrelson's work in the film earned him his first (much deserved) Best Supporting Actor Oscar nomination.
1Zombieland
Harrelson understood exactly what was needed for his part as Tallahassee in this all-time horror comedy—which follows a group of strangers road-tripping across a zombie-infested America. He made his sadistic, Twinkies-loving character lovable, badass, and downright unforgettable.
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