Best Woody Harrelson Movies, Ranked

Woody Harrelson is once again making waves in the world of cinema after his latest movie Triangle of Sadness won the prestigious Palme d’Or award and received an eight-minute standing ovation at the Cannes Film Festival. The dark comedy marks the English-language debut from the Swedish director Ruben Östlund and stars Harrelson as the raging Marxist captain of a cruise ship for the mega-rich.

A self-proclaimed anarchist, hemp activist, and all-around free spirit, Harrelson’s career in Hollywood has been as varied and unpredictable as one would expect from the man whose run-in with the law in the UK was later the plot for a feature film (starring Harrelson himself). Since his early days in acting, where he won the nation’s hearts playing Woody Boyd on hit sitcom Cheers, he’s gone on to appear in dozens of feature films, ranging from erotic thrillers to hit romantic comedies to all-out action adventures.

More often than not, though, Harrelson’s characters are unconventional — sometimes unhinged. Feeling just as at home in lower-budget independent movies as he does in huge blockbusters, Harrelson seems to revel in finding humor in some of the darkest places, a theme that runs through a lot of the movies on this list. With his southern drawl and inimitable charisma, Harrelson’s fine and expansive repertoire is home to some of the greatest movies of the last few decades. Here are his eight best, ranked.

8 Seven Psychopaths

The first, but not the only, movie on this list directed by Martin McDonagh, Seven Psychopaths is a violent and intelligent satire full of pitch-black comedy and engaging dialogue, à la Quentin Tarantino. Harrelson stars alongside some of Hollywood’s finest actors including Colin Farrell, Sam Rockwell, Abbie Cornish, and Christopher Walken. The branching story touches on numerous topics and themes, but as far as Harrelson is involved, he plays a violent and unpredictable gangster searching for the perpetrators of a dognapping committed against his beloved Shih Tzu. Harrelson is unnaturally convincing playing these types of unhinged characters so was quite at home in what is otherwise an utterly berserk, but thoroughly entertaining crime thriller.

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7 White Men Can’t Jump

Having already won the nation’s heart as Woody Boyd in Cheers, it was clear Harrelson was destined for big things. While White Men Can’t Jump wasn’t his first foray into cinema — he had appeared in a few other movies prior including the sports comedy Wildcats alongside Goldie Hawn — it was certainly the movie that cemented him as a serious force to be reckoned with. Along with co-star Wesley Snipes (who had also appeared with Harrelson in Wildcats) the pair became certified superstars, with the movie becoming a hit with critics and audiences alike. The basketball-based buddy comedy had just enough heart and humor to leave a long-lasting legacy in Hollywood, with the movie still being referenced in popular culture to this day. It has recently been announced that a remake is in the works, starring rapper Jack Harlow and NFL player Ryan Kalil.

6 Kingpin

From one sports comedy to another, Kingpin may not have been the worldwide hit that White Men Can’t Jump was — it received mixed reviews from critics at the time of its release and barely recuperated its budget at the box office — but it has since gone on to be re-appraised and amassed a cult following. The sport in question here is ten-pin bowling, with the somewhat surreal storyline focusing on Harrelson’s character, an alcoholic ex professional bowler who becomes the manager of a promising Amish bowler played by Randy Quaid. While, once again, Harrelson shines in this off beat quirky comedy, Bill Murray’s appearance as rival bowler “Big Ern” McCracken, in all his insane comb over glory definitely deserves an honorable mention in any article on the topic of Kingpin.

5 The People vs. Larry Flynt

The movie that earned Harrelson his first Academy Award nomination sees him delivering a tour de force performance as American pornographer Larry Flint, as it chronicles his battles with political, legal, and religious institutions. Aside from Harrelson, the supporting cast including Edward Norton and Courtney Love all turned in astounding performances that saw them receiving multiple accolades and high praise from critics across the globe. Harrelson’s undeniable charisma shines through as he takes the audience on a wildly entertaining trip through the life of one of America’s most notorious entrepreneurs. (Interesting tidbit: Woody Harrelson’s on-screen brother in the movie is played by his real-life brother Brett Harrelson).

4 Natural Born Killers

One of the most controversial movies of all time, Natural Born Killers follows the exploits of Mickey and Mallory, a couple of lovers on a killing spree. The original screenplay was written by Quentin Tarantino and the movie was directed by Oliver Stone. It certainly possesses artistic traits of both, but Tarantino has later disowned the film, stating that the finished product bears little resemblance to his screenplay. Nonetheless, it’s a white-knuckle rollercoaster ride of a film full of violence, action, dark humor, and satire, particularly taking aim at how the media glorifies violence, while simultaneously arguably doing the same. The acting from the two leads is impressive in how relatable yet utterly unhinged they manage to portray the killers, and the rest of the cast including Tommy Lee Jones, Robert Downey Jr, and Tom Sizemore also turn in top-notch performances. There is a particularly disturbing scene in which comic legend Rodney Dangerfield plays the abusive patriarch in the style of a TV sitcom, which has to be seen to be believed.

Related: 10 Best Oliver Stone Films, Ranked

3 Zombieland

Post-apocalyptic zom-com Zombieland is by far one of the most successful movies when it comes to mixing horror with comedy. It’s got enough action, scares, headshots, and blood to keep even the most avid of gore hounds satisfied, but the cocksure comedy never eases up and remains at the present throughout. It’s full of visual gags involving the zombies themselves and situation comedy revolving around the three lead characters and their clashing personalities. Harrelson plays the gun-toting outlaw type, Tallahassee; Jesse Eisenberg plays to type as the far more conservative, somewhat neurotic Columbus; and Emma Stone acts as the strong-willed, slightly sassy Wichita. Harrelson is also once again reunited with Hollywood royalty Bill Murray in what has to be one of the most memorable cameos in movie history.

2 No Country for Old Men

The sparse, minimalist landscape of the Texas desert peppered with the nihilistic dialogue were not ingredients that screamed box office success and Oscar glory. And yet, the Coen Brothers added another masterpiece to their already tight oeuvre with No Country for Old Men. With a tour de force performance of pure evil manifest, Javier Bardem wanders from place to place killing anyone and everything in his path while going on philosophical diatribes about the importance of the coin toss. “Call it Friendo”. Harrelson plays a grizzled operative hired to take him down. His limited screen time doesn’t alter the fact that, after Bardem’s, Harrelson’s character might just be the most intriguing character in this highly intriguing and visually rewarding movie.

1 Three Billboards Outside Ebbing, Missouri

Director Martin McDonagh’s second entry on this list, Three Billboards Outside Ebbing, Missouri, at the heart of it, is a highly dramatic and emotion laden dark crime thriller about a woman who rents three roadside billboards to call attention to her daughter’s unsolved rape and murder. Despite the dark subject manor, McDonagh still manages to sneak in a few glimmers of hope and laces it with an underlying darkly comedic tone. The entire movie is a masterclass in acting, with Frances McDormand and Sam Rockwell sweeping up at the awards ceremonies. Harrelson, playing a supporting role, was still recognized for his heart-rending, multi-layered portrayal of the cancer-suffering Sheriff, and was nominated for an Oscar, SAG, and BAFTA for his performance.

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