Woody Harrelson’s career has seemingly spanned from “aw shucks” to “I don’t give any f**ks.”
After rising in stardom for his run on the incredibly successful sitcom Cheers to a run of bold choices including Natural Born Killers, the man many simply call “Woody” has shown he doesn’t shy away from controversy. Sometimes that’s a great thing, like when he’s advocating for legalizing cannabis, and other times it’s controversial. See his hot takes against just about every president and being a self-proclaimed anarchist, and still, sometimes it’s just a bit off-putting (see: recent rants on Saturday Night Live).
Throughout his decades in Hollywood, the 61-year-old native Texan has had a unique ability to showcase characters in an interesting light while being able to manipulate emotions with his eyebrows and smirks alone. Harrelson’s still hard at work, with his memorable (for many reasons) stint in Venom: Let There Be Carnage, work in Triangle of Sadness, and even Netflix’s The Man from Toronto.
What’s the best of Woody, though? Here are Harrelson’s 15 best movies and TV shows — ranked, naturally.
15. LBJ (2016)
LBJ wasn’t even the best movie about President Lyndon Baines Johnson in 2016, with that honor going to the excellent All the Way starring Bryan Cranston. However, while LBJ as a whole isn’t great, Harrelson is excellent in it.
Johnson was a strange, eccentric man and Harrelson channels that, bringing his A-game while keeping the character broadly realistic. There aren’t too many people who can capture the weirder sides of Johnson, but Harrelson does it with aplomb (even through some slightly distracting make-up).
14. Game Change (2012)
Harrelson has frequently dipped his toe into political drama, as well as periodically playing Joe Biden on Saturday Night Live!. But it’s in 2012 HBO movie Game Change that he really shines. This dramatizes John McCain’s 2008 presidential campaign, with Ed Harris as McCain and Julianne Moore as Sarah Palin. Harrelson plays Steve Schmidt, with the movie seeing him become gradually more and more alarmed by Palin’s odd behavior and inexperience.
Harrelson picked up several nominations for his performance, including nods from the Screen Actors Guild, the Golden Globes, and the Emmys.
13. The Thin Red Line (1998)
Terrence Malick’s arty World War II movie is very much an ensemble movie with a truly star studded cast including Sean Penn, Adrien Brody, Jim Cavaziel, Jared Leto, George Clooney, John Cusack, Nick Nolte, and John Travolta (among many others). But even amongst this glittering cast Harrelson makes an impact.
Harrelson plays a Sergeant who fumbles throwing a hand grenade while under fire, pulling the pin while it’s attached to his belt. At first, the scene is vaguely comedic as he exclaims “I blew my butt off!” Things rapidly get serious as he realizes he’s going to die from his injury and demands his men tell his wife ” I died like a man” before he bleeds out.
12. The Messenger (2009)
The Messenger proves once again that Harrelson is a perfect fit for military dramas. This Oscar-nominated performance sees Harrelson as Captain Tony Stone, a casualty notification officer (i.e. the person who informs a soldier’s family of their death). Despite the morbid subject matter, it’s continually interesting, with Harrelson and co-star Ben Foster having great chemistry.
Harrelson would go on to receive many nominations for his performance, though lost to Christoph Waltz for Inglourious Basterds. And, let’s face it, nobody that year was going to beat him.
11. No Country for Old Men (2007)
Javier Bardem’s Anton Chigurh sucks almost all the oxygen out of the room in No Country for Old Men and was rightly garlanded by just about every awards body. However, Harrelson’s bounty hunter Carson Wells is also very much worthy of recognition.
What’s particularly interesting about Harrelson’s performance here is that he’s effectively playing his real-life father Charles Harrelson, who was a hitman once suspected of being involved in the Kennedy assassination. Author Cormac McCarthy even directly referenced Charles’ murder of a judge in the original novel, making for a strange synchronicity between fact and fiction. Harrelson formed a relationship with his father in prison and the film was eventually released just two months after he died behind bars.
10. TransSiberian (2008)
Maybe one of Harrelson’s lesser-known movies, it’s worth checking out if you missed the train (sorry) the first time around. Harrelson and costar Emily Mortimer are superb in the psychological thriller and give their characters a vividness that the audience can invest in. The story follows the duo as a couple who wind up in possession of matryoshka dolls (better known as Russian nesting dolls) that are filled with heroin. The suspense that leads to the premise, and the fallout from it, are captivating to the very end.
9. The People vs. Larry Flynt (1996)
The core themes of the movie might not be for everyone – namely, pornography, and the fight for supposed freedom of speech – but the performances by Harrelson and Courtney Love (seriously) still stand up today. Harrelson plays the titular Flynt, who founded the pornographic magazine Hustler, and his fight with the legal system, moral opposers, and of course his own inner demons, to make the magazine successful and legal. Love plays Althea Leasure, a stripper who becomes Flynt’s love interest and even advocate and caretaker.
8. Kingpin (1996)
As a movie, no, this shouldn’t be in any top 10 lists, really (unless it’s the 10 best bowling movies), but Harrelson’s grandiose performance is a masterpiece. It’s quite a stark contrast to the other movies he put out in ’96, the aforementioned The People vs. Larry Flynt and The Sunchaser, but it’s the lighter, goofier side he probably needed to keep exploring and use to offset the more serious roles.
Harrelson plays an alcoholic ex-professional bowler, Roy Munson, who takes a budding bowler under his wing, the Amish Ishmael Boorg (Randy Quaid). A lot of hijinks, highs, and lows follow, with some gags that still get laughs today, but the movie lacks a tighter script and maybe could’ve benefited from better casting for the third star in the film, Vanessa Angel.
7. Three Billboards Outside Ebbing, Missouri (2017)
An incredibly intense movie (and subject matter) with equally intense and powerful performances from the three main stars of the movie — Frances McDormand, Sam Rockwell, and Harrelson — that garnered a lot of award nominations and wins. In the movie, Mildred Hayes (McDormand) is livid and distraught after the assault and murder of her daughter remained unsolved, and she rents three billboards calling out the police chief, Bill Willoughby (Harrelson). Willoughby, who is battling pancreatic cancer, increases his efforts to solve the crime as the town around them grows incensed at the billboards and tries to pressure them into taking the signs down and distracting from the case.
6. The Hunger Games series (2012-2015)
The original movie was a phenomenon, and the sequels were pretty great as well. Harrelson played Haymitch Abernathy, who was just askew of the heart of the story throughout the series as a guide and sometimes role model for the main protagonists, Katniss Everdeen (Jennifer Lawrence) and Peeta Mellark (Josh Hutcherson), despite his rampant alcoholism and self-destructive nature.
The premise of the series revolves around a futuristic nation called Panem that is controlled by the Capitol. Panem once tried to revolt and the current 12 districts of the nation must undergo a tournament each year as punishment, in which a boy and girl between the ages of 12 to 18 years old must be selected to fight to the death; this tournament is known as the Hunger Games, and it plays out on television for all to see. Katniss and Peeta are from a poorer district, District 12, and are the unlucky contestants for the games in the first movie, with the stakes and drama ramping up as the series plays out.
5. Cheers (1985-1993)
It’s hard to pinpoint whether this should be a little lower or even higher on the list, because of the power and persistence of Cheers. The show lasted in reruns long, long after it stopped airing, and it’s still held in high esteem as one of the best shows in history. Harrelson definitely played a part in that as a mainstay on the show after joining in the fourth season; he played that midwest charm to a T as the bartender with the same name.
4. True Detective (2014)
A legitimate epic neo-noir crime saga, True Detective was so enthralling it spawned sequels that unfortunately didn’t come close to meeting the standards of the original. Playing Martin “Marty” Hart opposite Matthew McConaughey’s Rustin “Rust” Cohle, there was sizzling chemistry between the two and gripping dialogue amid all the chaos, tragedy, and near redemption. We’re sure that the duo, while providing mesmerizing performances on the show, had a good time together off-screen considering some of their shared interests.
The first season of True Detective features Rust and Marty investigating what turns out to be an intricate occult spiral they were investigating 17 years before picking up the narrative in the present day. They find links to unsolved crimes as they both struggle with their past. The first season is also full of gorgeous cinematography and one of the most famous scenes to hit TV — the tracking, lengthy one-shot sequence masterfully done by Cary Joji Fukunaga.
3. White Men Can’t Jump (1992)
Harrelson plays said white man from the title of the movie, and for anyone who’s seen the movie, it’s clearly about a lot more than basketball. The film expertly sifts through romantic relationships, friendships, race relations, athletic endeavors and what that brings out in people, as well as exploring the paths people go down when they are fighting the feeling of needing to prove themselves.
Harrelson plays Billy Hoyle, a former college basketball standout who now makes it by hustling on the streetball courts, playing to the stereotype he won’t be any good because he is white. Eventually, he meets up with Sidney Deane, who is a fellow streetball player bested by Hoyle before the two decide to team up to hustle others as a running bit.
On the side of that, Hoyle and his girlfriend, Gloria (Rosie Perez), are on the run from mobsters because he owes them money, and all the while, she is striving to become a contestant on Jeopardy! of all things. The interplay between all the characters, including Sidney’s wife, Rhonda Deane (Tyra Ferrell), is engaging and the movie is still just as great today as it was when it came out.
2. Zombieland & Zombieland: Double Tap (2009, 2019)
Playing a character by the name of Tallahassee, Harrelson in Zombieland feels like the perfect example of what audiences probably think — or want — Harrelson to be like in real life, especially if there were zombies involved. Both films follow four characters named after their hometowns — Columbus (Jesse Eisenberg), Wichita (Emma Stone), Little Rock (Abigail Breslin), and Tallahassee — as they navigate a post-apocalyptic zombie world triggered by strains of mad cow disease that turned the majority of Earth’s humans into zombies.
At first, Columbus is on his own before he meets up with Tallahassee, who is brash, cocky, and prefers to be a loner. Eventually, the two encounter the other members of their soon-to-be tribe, Little Rock and Wichita, who trick them at first before the four begin to rally around each other to try and survive in their new reality. The sequel is solid because of the four stars, but the first film is the better movie of the two.
1. Natural Born Killers (1994)
We can’t quite call this Harrelson’s breakout movie role, because that was the previous entry, but it absolutely is the movie that made those in Hollywood and across America see Harrelson in a new light. Sometimes shocking and always riveting, Harrelson brought both menacing and loving qualities to the character of Mickey Knox.
The movie itself is a directorial masterpiece by Oliver Stone, with several incredible performances from Juliette Lewis, Robert Downey Jr., Tommy Lee Jones, and Tom Sizemore. In the film, Mickey and Mallory Knox (Harrelson and Lewis, respectively) become mass murderers triggered by their tragic childhood experiences and set in motion by a diner scene that turns violent before they set off on their spree. The media surrounding the duo makes them cult heroes. There are some hard-to-watch scenes in the movie, but all in all, it’s hard to turn away because the film is so well done.
