Some of my earliest childhood memories oddly enough revolve around Woody Harrelson. It sounds strange, I know, but I vividly remember watching reruns of Cheers when I should have been sleeping or catching the White Men Can’t Jump trailer before some random movie on VHS at a friend’s sleepover. And ever since then, Harrelson’s body of work has played a fairly significant role in the direction of my life. I became obsessed with watching movies over and over again after catching Natural Born Killers (or at least the most sensational parts of it) at a neighbor’s house after school one day and decided I wanted to write for the school paper after watching No Country For Old Men on Thanksgiving Eve. The list could go on and on.
That being said, here are some of the best Woody Harrelson movies and TV shows to check out if you want to see what one of the most entertaining living actors is all about.
Triangle Of Sadness (2022)
A superyacht full of celebrities and other wealthy passengers becomes stranded on a desert island where everyone, including the tormented crew, is forced to fight for survival. That’s the basic premise for Ruben Östlund’s 2022 satirical black comedy, Triangle of Sadness, a film that was up for a total of four Academy Awards shortly after its release.
Woody Harrelson, who plays the ship’s drunk and off-kilter captain, is in top form throughout Triangle of Sadness. His performance, which had him take part in a chaotic and vomit-filled dinner scene, steals the show and once again proves that he’s one of the most talented actors around.
Stream Triangle of Sadness on Hulu.
Rent/Buy Triangle of Sadness on Amazon.
Buy Triangle of Sadness on Blu-ray on Amazon.
White House Plumbers (2023)
There have been countless movies and TV shows about the Watergate Scandal and its fallout, but the 2023 HBO original series, White House Plumbers, took a much different and far more humorous approach to one of the biggest political controversies of the 20th century. In the miniseries, Woody Harrelson plays E. Howard Hunt, a CIA officer who works alongside Justin Theroux’s G. Gordon Liddy to find the source behind the Pentagon Papers in a scheme that inadvertently led to the Watergate episode.
Harrelson, who has always been able to bounce between comedy and drama, is masterful in his portrayal of a morally ambiguous government figure, especially whenever he finds himself in the middle of some major disasters.
Stream White House Plumbers on Max.
Buy White House Plumbers on Amazon.
North Country (2005)
One of Charlize Theron’s best movies, the 2005 drama, North Country, tells the story of Josey Aimes (Theron), a Minnesota iron mine worker who files a sexual harassment lawsuit after her employer and male coworkers subject her to a vicious cycle of abuse and disturbing behavior in hopes she’ll quit her job.
Woody Harrelson comes into the picture as Bill White, a lawyer who takes up Aimes’ case and helps her get back at those who made her life a living hell just because she wanted to make a living for herself. The scene where Bill cross-examines Bobby Sharp (Jeremy Renner) on the witness stand happens to be some of Harrelson’s best acting.
Rent/Buy North Country on Amazon.
Buy North Country on DVD on Amazon.
War For The Planet Of The Apes (2017)
The final chapter in Matt Reeves’ sci-fi action trilogy, War for the Planet of the Apes features one last showdown between Caesar (Andy Serkis) and his army and a dangerous group of humans led by the tyrannical Colonel (Woody Harrelson). After the leader of the Alpha-Omega militia kills members of the ape leader’s family and closest friends, we’re on our way to full-on war.
Though he plays a downright evil and megalomaniacal character, it’s hard not to enjoy Harrelson’s performance in this 2017 thriller. It’s easy to tell that he was having just as much fun playing a dastardly villain as audiences had watching it in the theater.
Rent/Buy War for the Planet of the Apes on Amazon.
Buy War for the Planet of the Apes on Blu-ray on Amazon.
Champions (2023)
If you’re looking for a Woody Harrelson movie that has comedy, drama, and a whole lot of heart, then look no further than Champions. This 2023 inspirational sports film follows Marcus Marakovich (Harrelson), a hot-tempered basketball coach who agrees to lead a team of intellectually disabled players instead of an 18-month prison sentence. Little does he know, but Marcus’ life is about to change… for the better.
This great sports underdog story has all the hallmarks of the genre, and features some killer laughs, emotionally driven drama, and some awesome basketball sequences. Harrelson is both strong and vulnerable throughout, which adds a great deal to this heartwarming film.
Stream Champions on Prime Video.
Rent/Buy Champions on Amazon.
Buy Champions on Blu-ray on Amazon.
Cheers (1985 - 1993)
Although not one of the original members of the Cheers cast, Woody Harrleson’s dim-witted but beloved Hoosier bartender Woody Boyd quickly became one of the standouts of the long-running NBC sitcom with his introduction at the start of Season 4. After he arrives at Cheers to meet his “pen pal” Coach Emile Pantusso (Nicholas Colasanto), Woody learns of the former bartender’s passing from Sam Malone (Ted Danson) who subsequently offers him a job tending bar, and the rest is history.
Woody Harrelson would be nominated for five Primetime Emmy Awards for his Cheers performance, winning one for Best Supporting Actor in a Comedy Series in 1989. Not bad for his first television role.
Stream Cheers on Hulu.
Stream Cheers on Paramount+.
Stream Cheers on Pluto TV.
Buy Cheers on Amazon.
Buy Cheers on DVD on Amazon.
White Men Can’t Jump (1992)
In the spring of 1992, Woody Harrelson went from one of the most familiar faces on TV to a promising movie actor with Ron Shelton’s sports comedy White Men Can’t Jump. In the all-time great basketball movie, Harrelson plays Billy Hoyle, a white basketball player who uses his opponents' underestimation of his skills on the court to make big money. One of these hustles puts him face-to-face with Sidney Deane (Wesley Snipes), who sees the potential of the scheme and partners up with Hoyle to take the scheme all across Los Angeles.
If Cheers put Woody Harrelson on the map, White Men Can’t Jump made him one of the most recognizable faces in young Hollywood and took things to the next level.
Stream White Men Can’t Jump on Max.
Rent/Buy White Men Can’t Jump on Amazon.
Buy White Men Can’t Jump on DVD on Amazon.
Natural Born Killers (1994)
Directed by Oliver Stone and based on a story written by Quentin Tarantino, the 1994 psychedelic crime drama, Natural Born Killers, tells the story of Mickey (Woody Harrelson) and Mallory Knox (Juliette Lewis) two young lovers who stop at nothing to be together, even if that means killing 52 people on a cross-country crime spree that makes them terrifying serial killers to some and cult heroes to others.
The brilliant thing about Natural Born Killers, well, besides the cast that also includes Robert Downey Jr., Tom Sizemore, and Tommy Lee Jones, is the fact that remains just as relevant now as it was upon its release 30 years ago. Through its attacks on society’s obsession with serial killers and a media with an “if it bleeds, it leads” mentality, Stone’s controversial thrill ride is at times enlightening as much as it is frightening.
Rent/Buy Natural Born Killers on Amazon.
Buy Natural Born Killers on 4K UHD on Amazon.
The People Vs. Larry Flynt (1996)
On Christmas Day 1996, Miloš Forman gave the world of cinema an unexpected gift in the form of a biographical drama about one of the most unconventional crusaders for free speech this country has ever seen: Hustler magazine founder and provocateur, the late Larry Flynt. In The People vs. Larry Flynt, we see Woody Harrelson take on the role of the famed pornographer as he and his attorney Alan Isaacman (Edward Norton) take a case involving decency laws all the way to the United States Supreme Court.
Oddly inspirational and undoubtedly hilarious, The People vs. Larry Flynt is a biopic befitting of the prominent media figure, especially with the Academy Award-nominated performance of Woody Harrelson and his commitment to the larger-than-life character.
Stream The People vs. Larry Flynt on Paramount+.
Rent/Buy The People vs. Larry Flynt on Amazon.
Buy The People vs. Larry Flynt on Blu-ray on Amazon.
Three Billboards Outside Ebbing, Missouri (2017)
Martin McDonagh’s 2017 crime drama Three Billboards Outside Ebbing, Missouri, tells the story of Mildred Hayes (Frances McDormand), a woman who will stop at nothing to get justice for her daughter who was raped and murdered several months earlier. Not happy with Police Chief Bill Willoughby’s (Woody Harrelson) investigation that hasn’t turned up any leads, Hayes takes out three billboards outside of town in hopes of getting everyone’s attention. What follows is a tale of determination and redemption in the face of evil and injustice in a small Midwestern town.
Woody Harrelson was nominated for an Academy Award for Best Supporting Actor (which was won by his co-star Sam Rockwell) for his portrayal of a character who is forced to look at his own mortality dead in its eyes while also facing the biggest professional crisis of his career. While not the most likable character, Harrelson’s performance is beautiful if not a little tragic.
Rent/Buy Three Billboards Outside Ebbing, Missouri on Amazon.
Buy Three Billboards Outside Ebbing, Missouri on DVD on Amazon.
True Detective (2014)
Told over the course of 17 years and two timelines, True Detective Season 1 follows Louisiana State Police homicide detectives Rustin “Rust” Cohle (Matthew McConaughey) and Martin “Marty” Hart (Woody Harrelson) as they investigate the gruesome murder of a young prostitute. As their investigation carries on, the two detectives are forced to reckon with the nature of the case, those who may or may not be involved, and how the uncertainty and brutality of it all impacts them on a personal and spiritual level.
One of the best set of episodes of television of the 21st Century, the first season of Nic Pizzolatto's HBO crime anthology series has great writing, direction byCary Joji Fukunaga), and acting from its leads as well as supporting roles.
Stream True Detective on Max.
Buy True Detective on Amazon.
Buy True Detective on DVD on Amazon.
No Country For Old Men (2007)
What starts as a normal day of hunting in the West Texas desert turns into anything but when Llewelyn Moss (Josh Brolin) stumbles across the aftermath of a drug deal gone bad. After discovering a bag of cash, the Vietnam War veteran becomes the hunted when ice-cold assassin Anton Chigurh (Javier Bardem) comes looking for the lost drug money. What follows in No Country For Old Men, one of the best Western films is a cat-and-mouse chase through the small towns and wide-open spaces of the U.S.-Mexico border.
Just when it doesn’t look like No Country for Old Men could get any better (and deadlier), contract killer Carson Wells (Woody Harrelson) makes his big debut as a hired gun sent in to find the missing money and take out Chigurh, even if it’s only for a few minutes.
Stream No Country for Old Men on Paramount+.
Stream No Country for Old Men on Pluto TV.
Rent/Buy No Country for Old Men on Amazon.
Buy No Country for Old Men on Blu-ray on Amazon.
The Messenger (2009)
The 2009 military drama The Messenger centers on Will Montgomery (Ben Foster), an injured Iraqi War veteran who joins the U.S. Army’s Casualty Notification service alongside Tony Stone (Woody Harrelson). Together, the pair bring families the news no one wants to hear about their sons, daughters, mothers, or fathers. An already tough job is made even more difficult when Will crosses the line with a soldier’s widow.
Woody Harrelson received multiple nominations for his portrayal of the war-torn and emotionally battered Tony Stone and was more than deserving of them all. His pairing with Ben Foster also makes for a great mentor-mentee dynamic that adds much of the emotional weight to this heartbreaking modern war film.
Stream The Messenger on Peacock.
Stream The Messenger on Plex.
Stream The Messenger on Pluto TV.
Stream The Messenger on Tubi.
Rent/Buy The Messenger on Amazon.
Buy The Messenger on Blu-ray on Amazon.
Kingpin (1996)
Years after losing his hand in a con gone wrong, bowler Roy Munson (Woody Harrelson) finds a second chance at fame, glory, and tons of cash, when he takes Amish bowler Ishmael Boorg (Randy Quaid) under his wing. Along the journey, however, Munson comes face-to-face with the man who cost him his career all those years earlier: the scheming Ernie McCracken (Bill Murray).
Despite being one of the Farrelly Brothers movies that doesn’t seem to get talked about as much as the others, Kingpin isn’t one that you should miss. It also features two of the ‘90s cinema’s best scumbags: Roy Munson and Ernie “Big Ern” McCracken.
Rent/Buy Kingpin on Amazon.
Buy Kingpin on Blu-ray on Amazon.
Zombieland (2009)
Released at the peak of the early 21st-century zombie craze, Ruben Fleischer’s 2009 horror comedy Zombieland follows a party of four survivors — Tallahassee (Woody Harrelson), Columbus (Jesse Eisenberg), Wichita (Emma Stone), and Little Rock (Abigail Breslin) — as they drive across the country in hopes of reaching Los Angeles where they believe there’s a chance of making it through the undead nightmare. And while safety and security are what they seek, the four quickly find something more: family.
One of the best things about Zombieland (besides its cast and that excellent cameo near the end) is the way it blends elements of comedy, drama, and horror to create this emotionally complex story about survival in the face of certain death. And you’ll never look at Twinkies the same.
Stream Zombieland on Apple TV+.
Rent/Buy Zombieland on Amazon.
Buy Zombieland on DVD on Amazon.
The Edge Of Seventeen (2016)
The 2016 coming-of-age drama The Edge of Seventeen follows awkward, depressed, and disruptive high school junior Nadine Franklin (Hailee Steinfeld) as she tries to find meaning, purpose, and a new support system when her best friend and older brother start dating each other. After striking up a friendship with her teacher Max Bruner (Woody Harrelson), Nadine begins to experience a great deal of change on multiple fronts on an extremely personal journey.
The Edge of Seventeen is made all the better with the pairing of Woody Harrelson and Hailee Steinfeld. There are points in the movie when it feels like you’re watching an actual student and teacher open up with one another, as opposed to two actors on a set, their performances are that effective.
Stream The Edge of Seventeen on Netflix.
Rent/Buy The Edge of Seventeen on Amazon.
Buy The Edge of Seventeen on DVD/Blu-ray on Amazon.
After looking back on all those great Woody Harrelson movies and TV shows, I know how I will fill up my nights while I wait for all those 2024 new movie releases to make their way to my local theater (or streaming service).
