Woody Harrelson's decades-long career in Hollywood has seen the celebrated actor appear in everything from action blockbusters to prestige biopics, and his best movies include a wide range of characters and performances. First making a name for himself as Woody Boyd in 200 episodes of the TV sitcom Cheers, Harrelson quickly jumped to the big screen where he began turning heads in supporting roles in early '90s films like Doc Hollywood and L.A. Story. As his resume continued to grow, he was eventually tapped to play leading roles in successful movies, some of which nabbed him Oscar nominations and a slew of other critical accolades.
Harrelson's distinct performance style has helped him stand out, and even when playing a smaller role he's never struggled to be recognized. In Harrelson's more underrated roles, the actor always managed to work his magic and could elevate a project just with his presence in the movie or show. Regardless of whether he appeared in understated indie films like The Messenger or bombastic comic book movies like Venom: Let There Be Carnage, there was never any doubt whether Harrelson would put his best foot forward in bringing his character to life. Here, though, is a spotlight on Woody Harrelson's very best movies, ranked.
10 North Country (2005)
Many of Woody Harrelson's more memorable performances are in over-the-top movies that showcase his comedic edge, but North Country proved his dramatic chops weren't to be dismissed either. Based on a true story, the adaptation concerns Josey Aimes, played in the movie by Charlize Theron, who lodges a formal complaint against the sexual harassment she received while working in an iron mine. The performances of Theron and co-star Frances McDormand received Oscar nominations, but Harrelson's turn as the crusading lawyer Bill White sadly went unrecognized. The movie fared decently with critics, scoring a 69% on Rotten Tomatoes, but its performances far outshone the shortcomings of its script.
9 Now You See Me (2013)
Never a stranger to genre pictures, Woody Harrelson fits right in with the impressive ensemble cast of Now You See Me. The story regards a quartet of magicians who are hounded by FBI and Interpol agents while committing a series of massive heists. Harrelson co-stars as Merritt McKinney, a mentalist who lost all of his money in the past. Director Louis Leterrier, best known for the MCU's The Incredible Hulk, had another hit on his hands, and Now You See Me grossed an impressive $350 million against a $75 million budget, making it one of the highest-grossing movies of 2013 despite not being from a major franchise.
8 Triangle Of Sadness (2022)
Even after four decades in Hollywood, Woody Harrelson still has the ability to surprise, and he isn't above taking a smaller but juicier role in films like Triangle of Sadness. While sailing on a luxury yacht, a group of wealthy elite becomes stranded on an island and reverts to their baser instincts. The film won the prestigious Palme d'Or when it premiered at the Cannes Film Festival, in part for its biting satire of the rich. Harrelson's role as the Communist theory-espousing captain is a source of great humor in the film, and he lends a modicum of Hollywood celebrity to a cast made up mostly of unknowns and newcomers.
7 No Country For Old Men (2007)
Working with the legendary Coen brothers was yet another feather in Harrelson's cap, and their collaboration in No Country for Old Men once again proved his strength as a supporting actor. After finding a briefcase full of money in the desert, an average Joe, played by Josh Brolin, is stalked by a vicious cartel assassin to retrieve the cash. Harrelson played Carson Wells, another goon after the money, and his brief appearance and death are another shock among the many twists and turns ahead of No Country for Old Men's divisively quiet ending. The movie won four Oscars, including Best Picture.
6 Kingpin (1996)
Unlike many other Hollywood stars, Woody Harrelson's filmography is stuffed with just as many classic comedies as dramas, and Kingpin features Harrelson at his clownish best. The movie concerns a former professional bowler who attempts to ride the coattails of his new protégé back to the top. Directed by the Farrelly brothers, Kingpin was a typical '90s comedy, and Harrelson understood the verbose tone of the movie while playing Roy Munson. Though it only garnered a 49% score on Rotten Tomatoes, it was praised by critic royalty Gene Siskel and Roger Ebert, who both went against the trend in giving it thumbs up.
5 Zombieland (2009)
Memorable for its many zombie survival rules, Zombieland is an irreverent comedy that capitalized on the popularity of the undead in the late-2000s. The story follows a group of survivors who travel across the United States looking for a safe haven. Harrelson played Tallahassee, a hardened survivalist with an addiction to Twinkies and a dark past. Zombieland was a rare specimen because it cleaned up at the box office by grossing $102 million against a $23 million budget while simultaneously garnering critical praise with an aggregated Rotten Tomatoes score of 89%. It was the highest-grossing zombie movie before being toppled by World War Z in 2013.
4 Natural Born Killers (1994)
Oliver Stone's Natural Born Killers is a divisive movie, even hated by its original screenwriter, Quentin Tarantino, but it helped Woody Harrelson break into the mainstream. Its story follows a couple who goes on a murderous rampage and become celebrities after an attack that leaves them traumatized. At the time of its release, many audience members only knew Harrelson from Cheers, and his turn as Mickey Knox was a shocking reversal. Commenting on the nature of violence and the obsession with true crime, Natural Born Killers uses its bloodshed in a way that turned off many critics. Nevertheless, it became a cult classic and cultural touchstone for the 1990s.
3 The Messenger (2009)
First-time director Oren Moverman delivered an underrated movie with The Messenger while enlisting the former Cheers funny man to carry the emotional weight of its story. Ben Foster stars as a troubled Iraq War veteran who becomes a casualty notification officer along with his Gulf War veteran mentor, played by Woody Harrelson. Though Harrelson isn't the lead, his take on Captain Tony Stone is the glue that holds the film together. Unfortunately, The Messenger was a box office flop, grossing only $1.5 million, but it was critically well-received and even earned Harrelson his second Oscar nomination, this time in the Best Supporting Actor category.
2 Three Billboards Outside Ebbing, Missouri (2017)
Woody Harrelson's co-starring credit as police chief Bill Willoughby in Three Billboards Outside Ebbing, Missouri, one of director Martin McDonagh's best movies, earned the actor a slew of prestigious awards and nominations. The story chronicles the increasingly confrontational efforts of a woman to get her local police department to catch the person who killed her daughter. Harrelson flourishes in McDonagh's signature mix of drama and comedy, and his turn as Willoughby shows off both sides of his acting talent. Though he lost to his own co-star, Sam Rockwell, for the Best Supporting Actor Oscar that year, Harrelson's third nomination was further confirmation of his quality as a seasoned performer.
1 The People Vs Larry Flynt (1996)
Audiences had seen a lot of Woody Harrelson by 1996, but his portrayal of pornography mogul Larry Flynt in Miloš Forman's biopic showed he was a chameleonic performer as well as a character actor. The People vs. Larry Flynt chronicles the life of its titular figure from his days as a nightclub owner to his radical defense of free speech. Even opposite a cameo from Flynt himself, Harrelson is Flynt so convincingly that it elevates what's already an exceptional movie. Harrelson earned his first Oscar nomination, for Best Actor, and though he lost, this was evidence of how far he'd come in just a few years of working in movies.