The delightfully quirky and dynamic actor Woody Harrelson is known for portraying colorful characters and embracing any genre of film. A respected star of both the big and small screen, the performer has appeared in countless award-winning programs and pictures, first rising to prominence as Woody Boyd on the beloved sitcom Cheers.
He would go on to craft a prominent film career, starring in outstanding cinematic staples like White Men Can’t Jump, Natural Born Killers and The People vs. Larry Flynt. Harrelson has worked with some of the most revered directors and actors in the entertainment industry, working under Spike Lee, Milos Forman, Barry Levinson, Richard Linklater, Terrence Malick, Robert Altman, the Coen brothers, and numerous others.
Harrelson recently played a mad Marxist ship captain in Triangle of Sadness, which won the highest award at the 2022 Cannes Film Festival; his next project will be alongside Kevin Hart in the upcoming Netflix action comedy The Man from Toronto. With an Emmy and two Screen Actors Guild Awards, three Academy Award nominations, and four Golden Globe nominations, it’s safe to say that he’s both consistently acclaimed and consistently prolific; Harrelson has been credited in a whopping 29 films in just the last decade alone. .
However, it’s very hard to pin the actor down. He’s played a wide variety of roles, though he’s perfectly honed a few styles throughout the years.
Woody Harrelson the Funny Southern Charmer
20th Century Fox
Woody Harrelson actually began as pretty much a directly comedic performer; he was a good actor from the beginning and charmed with his Southern wiles, but his actual beginnings are mostly in comedy. Launched to fame with Cheers, where he played the ditzy bartender Woody Boyd, Harrelson perfected his brand of handsome humor. He would take it to his first movie, Wildcats with Goldie Hawn, and to an early rom-com in his career, Cool Blue.
His first great movie role was when Harrelson appeared alongside Wesley Snipes in the 1992 sports comedy White Men Can’t Jump, in which the two talented actors portray streetball hustlers who team up to win money on the street courts of Los Angeles and in a basketball tournament with a $5,000 prize. In the ‘90s staple, Harrelson plays Billy Hoyle, a former college basketball player who makes a living hustling streetballers who assume he can’t shoot well because he’s white; when he crosses paths with the cocky but gifted Sidney Deane, the pair join forces to start a business partnership and hustle the courts of California.
Former basketball star and Hall of Famer Bob Lanier was hired to train Harrelson and Snipes for their roles, who later declared the performers reached Division II college basketball skill level. White Men Can’t Jump went on to earn critical and commercial success, with a reboot starring rapper Jack Harlow currently in the works, and most of this was due to the comedic charm Harrelson pulls off. He would continue to bring comedy to a variety of movies over the years, perhaps most significantly in the Farrelly brothers gross-out comedy classic Kingpin and the massive horror-comedy success story, Zombieland and its sequel.
Columbia Pictures
That sidesplitting 2009 comedy follows four vastly different survivors of a zombie apocalypse as they reluctantly join forces and set out on a road trip to California in hopes of discovering a rumored safe haven from the flesh-eating creatures in Los Angeles. In the uproarious flick, geeky college student Columbus (Jesse Eisenberg) meets the Twinkie-craving, zombie-killing mean machine Tallahassee (Woody Harrelson), with the duo partnering up in their search for a sanctuary. Zombieland was a knockout with both critics and audiences alike, with Harrelson’s performance being lauded as one of its fines; the Toronto Star wrote, “‘Nut up or shut up,’ is the most quotable of Woody Harrelson’s cowboy maxims in the genre mash-up Zombieland, and squeamish moviegoers should take it as gospel.”
Harrelson also memorably played a transvestite German prostitute who gets to slap the crap out of Adam Sandler in Anger Management, which was fun, and had a quirky, uncomfortably funny star turn as the titulat Wilson. Perhaps his most underrated role as a funny Southern charmer (though a much more nuanced and subtle performance) is in the great Paul Schrader film The Walker, where he plays an effeminate Southern gentleman who gets involved with a political scandal and murder. He’s surprisingly witty and delivers a delicious performance. Sometimes, Harrelson brings his ‘funny Southern charmer’ routine to the next skill he’s mastered: the wild man.
Woody Harrelson the Wild Man
Warner Bros.
Woody Harrelson shocked his fans and general audiences when he appeard in Oliver Stone’s controversial 1994 crime drama Natural Born Killers. The film follows two disturbed victims of childhood trauma who go on a violent murder spree across the country, attracting the attention of the media and becoming distressing news and tabloid fodder. Harrelson and Juliette Lewis famously appear as sensationalized serial killers Mickey and Mallory Knox, and Stone willfully cast Harrelson against type, since the actor had been primarily known for his comedic performances, a decision that helped mark a shift in the star’s career.
Suddenly, people could see the unstable spark in Harrelson’s eyes and his penchant for pitch-perfect, over-the-top, and truly wild performances. Shortly after Natural Born Killers, Harrelson delivered an all-time iconic performance, injecting this wild, unpredictable, and shocking persona with his comedic skills.
Depicting the rise to prominence of controversial pornographer Larry Flynt, the 1996 biographical drama The People vs. Larry Flynt chronicles the notorious Hustler publisher as he becomes embroiled in high-profile battles with both the law and religious institutions and becomes a protector of freedom of speech. Woody Harrelson was nominated for the Academy Award for Best Actor for his commanding performance of Flynt, inviting the polarizing businessman as his plus one when he was denied an invitation to the Oscars’ ceremony.
On his highly-buzzed about portrayal of the publisher, Harrelson told Yahoo! Entertainment, “I really came to like him, I don’t think I would’ve been much into doing the movie if I hadn’t come to respect Larry. I don’t respect much the pornography part of what he does, but what he is as a person, and the rebel that he is.” It’s this rebellious nature, the wild card Texan who refuses to play by the rules, which can also be seen in his performances in Zombieland and even The Hunger Games series, where he plays Haymitch Abernathy, the only living winner from Katniss’ district and a rebel at heart.
Another brilliant instance of Harrelson injecting his wild man with a bit of humor is the 2012 satirical black comedy Seven Psychopaths, in which Harrelson goes all-in with a hilarious performance alongside an A-list cast that includes Sam Rockwell, Colin Farrell, Christopher Walken, and Tom Waits.
CBS Films
The film centers on a struggling Los Angeles writer as he inadvertently becomes embroiled in the city’s crime underworld after his screwy but well-meaning buddies kidnap a notorious gangster’s cherished Shih Tzu. In the entertaining and off-the-wall flick, Harrelson masterfully plays the violent and erratic mobster Charlie Costello, who loves his beloved dog Bonny more than anything and will kill anyone who gets in his way of tracking her down and reuniting with the pooch.
Director Martin McDonagh praised the talented actor’s performance saying, “I’ve known Woody for years and years, and he was a perfect choice for this too. He’s got those great dramatic elements which he’s shown in Rampart recently, and he’s always been a fantastic comedian. You need that in this – someone who can be out-and-out funny, but also turn sinister on a dime.” This expertly describes Harrelson’s wild man.
Woody Harrelson the Quietly Intense Brooder
Oscilloscope Laboratories
Despite his ability to be hilarious or “turn sinister on a dime,” Harrelson is surprisingly great at manifesting melancholy in various roles which find him using his expressive face to the best of its abilities. Two of the greatest of these performances are his films with Oren Moverman.
Moverman made his directorial debut with the 2009 war drama The Messenger, telling the poignant story of injured Iraq soldier Will Montgomery (Ben Foster) as he returns home to finish his tour with the Army’s Casualty Notification service, working alongside the respected veteran officer Tony Stone (Woody Harrelson). Will finds his new mission complicated when he becomes romantically involved with a fallen soldier’s widow.
To prepare for production, the filmmakers worked alongside the United States Army in addition to the Walter Reed Medical Center to properly research military life, enlisting Lieutenant Colonel Paul Sinor to serve as a technical consultant for the drama. The Messenger premiered at the Sundance Film Festival where it was lauded by critics, with many calling it the best of Harrelson’s career; the actor was nominated for an Academy Award for Best Supporting Actor and won an Independent Spirit Award for his portrayal.
His other film with Moverman, Rampart, might not have been as universally acclaimed, but Harrelson’s performance certainly was. In his perfect review of the film, Roger Ebert writes, “Harrelson is an ideal actor for the role. Especially in tensely wound-up movies like this, he implies that he’s looking at everything and then watching himself looking.” Peter Travers of Rolling Stone concurred, writing, “it could have been a bucket of bleak. But the electric talent of Harrelson and Moverman is too exciting to be anything but exhilarating.” Harrelson’s dark, brooding turn as a corrupt cop is terrifying and multifaceted.
The actor played an entirely different cop in the Oscar-winning crime drama Three Billboards Outside Ebbing, Missouri, which found Harrelson re-teaming with writer/director Martin McDonagh from Seven Psychopaths. The film focuses on the efforts of determined mother Mildred Hayes as she rents three Missouri billboards to shame the police in an effort to solve her daughter’s rape and murder, leaving a pointed and controversial message for the local authorities.
Fox Searchlight Pictures
In the heartrending picture, Woody Harrelson portrays Ebbing police chief William Willoughby, who faces immense guilt over the unsolved crime and is secretly battling terminal pancreatic cancer. Three Billboards Outside Ebbing, Missouri earned numerous accolades and praise, with Time Out saying that it, “plays like a country ballad that’s full of improvised riffs on old themes: Its verses head off in different directions, some violent and swearing, others reflective and funny.” Frances McDormand is the pounding heart of the film, a fiery explosion in every scene she’s in, but Harrelson is the real soul of the movie. It’s a quiet, surprising, pained, and perfect performance of a suffering man trying to do what’s right as his world falls apart around him.
It’s clear from this cursory overview of Harrelson’s career that the actor has mastered his craft in not just one style but in many; he personifies what poet Walt Whitman meant when he wrote, “I contain multitudes.” Harrelson’s role in Triangle of Sadness is sure to be one of his best ‘wild man’ roles yet, and The Man From Toronto should find him tapping into that great comedic timing and handsome charm the star is known for. We can’t wait.
