Woody Harrelson is an actor who, once you see one performance, you’re want to track down everything else he’s ever done. The Texas native has a charming charisma about him, usually playing characters that do whatever they feel like doing. Harrelson’s father was convicted hitman Charles Voyde Harrelson, who was convicted of assassinating a federal judge. Prior to his conviction, he threatened to kill himself and claimed that he killed John F. Kennedy. With his father serving two life sentences, Woody and his two brothers grew up poor, living off his secretary mother’s wages. After graduating high school, he studied theater in Indiana and landed the role of bartender Woody Boyd in Cheers. He joined in the sitcom’s fourth season and remained until the show’s end, eight seasons later.

While still working on Cheers, Harrelson started his film career in 1986’s Wildcats alongside Goldie Hawn. Four years later, he starred in the 1990 romantic comedy Cool Blue. The ’90s was a great decade for him; he starred in White Men Can’t Jump, Money Train, Indecent Proposal, Natural Born Killers, and The People vs. Larry Flynt, among others.

Harrelson’s Surprise Brother

In 2023, Harrelson’s longtime friend and co-star Matthew McConaughey revealed that they could potentially be brothers from the same mother. McConaughey’s mother claimed to have been intimate with Harrelson’s father around the time of McConaughey’s conception. While appearing on The Late Show With Stephen Colbert, Harrelson said, “Well, I’ll just say there is some veracity to that thought.” While taking a joint vacation with Harrelson and McConaughey’s families, Matthew’s mom Mary let them know of the possibility.

When the topic of regrets came up, Harrelson recalled he said, “‘You know, it’s odd that my father has no regrets.'” That’s when “Ma Mac” told Woody, “‘I knew your father.’” He described Mary’s pause to be “filled with innuendo.” By doing the math, Harrelson said the year of McConaughey’s birth was nine months before his. “She was on a sabbatical from her relationship with his supposed father, Jim.”

See below our top five picks of Woody Harrelson’s best roles in film and television.

• 5. As Bill Willoughby in 'Three Billboards Outside Ebbing, Missouri'

  Though his role as Chief Willoughby was short-lived in this emotional crime drama, Harrelson’s character takes all the pressure and heat from Mildred Hayes (Frances McDormand) and her three billboards. He’s dying from pancreatic cancer, so he spends the perfect day with his loving family before taking his own life after they all go to bed. It makes for a powerfully heart-wrenching scene.

• 4. As Merritt McKinney in 'Now You See Me'

  With three other magicians, Harrelson’s Merritt McKinney is the standout. His charisma again shines as he takes on the role of a hypnotist, mentalist, and a self-proclaimed psychic. Merritt wants to rise again to his glory days as a famous magician as part of “The Four Horsemen.”

• 3. Tallahassee in 'Zombieland'

  We love Harrelson’s Tallahassee in 2009’s Zombieland. He delightfully gives no f—s in the post-apocalyptic zombie flick, but reluctantly joins Jesse Eisenberg’s Columbus. Tallahassee gets off on killing and torturing zombies, making for hilariously gory entertainment.

• 2. Billy Hoyle in 'White Men Can't Jump'

  Harrelson’s best movie role has got to be this sports comedy classic starring alongside Wesley Snipes. He makes for the perfect streetball hustler, Billy Hoyle, and loves to come off as humble, but has an air of arrogance about him. We highly recommend not wasting your time on the remake and instead, revisit the 1992 original.

• 1. Detective Martin 'Marty' Hart in 'True Detective'

  The top spot goes to Harrelson’s role as homicide detective Marty Hart. Starring alongside his buddy, Matthew McConaughey as Rust Cohle, their character’s relationship dynamic is tense as hell but fun to watch and Harrelson is the one who is the “voice of reason.”

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