He Came By It Honestly
Woody Harrelson has spent four decades playing bartenders, lawmen, and lunatics. But none of those roles compare to his real-life story. A hitman for a father, a potentially long-lost A-list brother, and a quirky rap sheet of his own—it has all made Harrelson Hollywood’s happiest outlaw.
1. He Shared More Than A Name
Woodrow Tracy Harrelson started making trouble in Midland, Texas, on July 23, 1961—exactly 23 years to the day after his father was born. Charles Voyde Harrelson had married Diane Lou Oswald in 1959 but by 1964 had all but abandoned Oswald and their three boys: Jordan, Woody, and Brett. Even so, Charles provided what he could as an encyclopedia salesman and gambler.
The cards, believe it or not, were the respectable half of his résumé.
2. His Father Walked Free
Woody Harrelson shared a birthday with his father—and a knack for breaking the law. The elder Harrelson (who was almost certainly guilty) went to trial for the 1968 slaying of Alan Berg. Thanks to his fancy defense attorney, a jury acquitted him of the charges. But Charles Harrelson couldn’t stay out of trouble any more than his movie-star-to-be son would be able to stay out of Hollywood headlines.
3. His Father Was Well Behaved
For movie stars, sequels are always a good thing—but not for Harrelson’s father. After his acquittal, Charles faced separate charges related to a pay-for-hire slaying in Texas in 1968. By 1973, a judge sentenced Charles to 15 years behind bars but released him just five years later for “good behavior”. Good behavior that didn’t last.
4. His Father Took Aim At A Judge
Less than a year after walking free, Harrelson’s father made himself infamous. A trafficker named Jimmy Chagra reportedly paid him $250,000 to keep the judge on his trial, John H Wood Jr, off the bench…for good. Then, on May 29, 1979, Charles did just that in a San Antonio parking lot. It was the first time anyone had executed a federal judge in the US since the turn of the century.
Harrelson would have to distance himself from his father’s legacy.
5. His Father Was Never Really Around
Harrelson’s mother deliberately shielded him from his father’s troubling legacy. In fact, Harrelson barely had any memories of his father. He later revealed that his father had all but disappeared from 1968 onward, and even then he described his father’s presence, saying, “Away and back. Away and back. It wasn’t like he was there all the time prior to that”.
But he would learn of his father’s deeds one way or another.
6. He Heard It On The Radio
Woody Harrelson didn’t learn the truth about his father until 1981—and he heard it from a total stranger. A 20-year-old Harrelson was listening to the radio when he came across a news broadcast about the misdeeds of one “Charles V Harrelson”. Curious, Harrelson asked his mother whether that was his father and she reluctantly told him the truth.
But he wouldn’t let his father’s legacy drag him down.
7. He Found A Stage In Indiana
Far from becoming a hitman like his father, Harrelson pursued the arts. He graduated in 1983 from Hanover College with a double major in theater and English. But it wasn’t all rehearsals and Shakespeare. Harrelson joined the Sigma Chi fraternity and later received an honorary Doctor of Humane Letters following his entertainment career.
He made some interesting friends, though.
8. He Befriended A Future Vice President
During a 2018 appearance on Jimmy Kimmel Live!, Woody Harrelson confirmed that he had been friends with then US Vice President Mike Pence while at Hanover. “I knew him,” Harrelson said. “We were both very religious…I remember I actually quite liked him. I thought he was a pretty good guy”. But Harrelson acknowledged that they had since gone their separate ways.
The way he went led straight to TV history.
Screenshot from Jimmy Kimmel Live!, ABC (2003-)
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9. He Filled An Empty Barstool
When Nicholas Colasanto succumbed to a heart attack in 1985, he left the opening for a role on an iconic TV series: Cheers. Instead of simply recasting the role, however, the show producers decided they wanted a “dumb” character to allow them to get away with expository dialogue. They even dreamed up the perfect name for this bone-headed barkeep: “Woody”.
Screenshot from Cheers, CBS Television Distribution (1982-1993)
10. He Was Cool As A Cucumber
Despite the fact that the character bore his name, Woody Harrelson didn’t seem all that interested in the Cheers audition. For starters, he walked into the studio blowing his nose. Then, as producer Peter Casey put it, Harrelson “looked like he could be trouble if you crossed him”, dressed in street clothes that looked like they belonged in his father’s closet.
Somehow, that only charmed the producers. Then Harrelson sealed the deal.
11. He Cried For Comedy
Even before Harrelson showed up, Cheers was a TV comedy classic. So, naturally, Harrelson auditioned by crying. Show producer Casey continued, “When Sam told him that Coach [passed], he teared up and started to cry”. Harrelson’s unexpected waterworks were just the right thing. “Whoa, he can really act,” Casey remembered thinking.
Just like that, Harrelson landed himself a role in TV history.
12. He Poured Drinks For Eight Years
Woody Harrelson turned his bartending role into a career-launching juggernaut. Joining Cheers in its fourth season, Harrelson’s Woody Boyd became a show favorite, sticking around until its last call in 1993. And he had more than empty bottles to show for it. Harrelson racked up five consecutive Emmy nominations between 1987 and 1991, winning in 1989 for Outstanding Supporting Actor in a Comedy Series.
His love life, meanwhile, was moving even faster than his fame.
Screenshot from Cheers, CBS Television Distribution (1982-1993)
13. He Married On A Whim
Harrelson got more than a starring TV role in 1985. He also got himself a bride, a wife, and a divorce. On a whim, Harrelson and Nancy Simon—the daughter of the playwright Neil Simon—tied the knot at a one-stop shop in Tijuana, Mexico. Neither husband nor wife was kidding themselves, though, and they planned on getting divorced the very next day.
There was just one small problem.
14. He Couldn’t Get A Divorce
When Woody Harrelson and Simon returned to the marriage parlor the next day to get their divorce, they were surprised to learn that, being Sunday, the business was closed. Instead, the marriage lasted 10 whole months. Harrelson later joked with USA Today, “I think at the time Neil was a little bit worried I might try to go after her money”.
True love, however, wasn’t far away.
15. His Assistant Became His Main Squeeze
Harrelson played fast and loose with his marriage to Simon, but when true love found him, he took his time. A lot of time. Harrelson first met his future second wife, Laura Louie, when she began working as his personal assistant on Cheers. Even though the couple had met in 1987, they wouldn’t make things official until years later.
He would have another wedding before then.
16. He Gave His Father A Second Chance
After learning about his father’s misdeeds, Woody Harrelson made a point to visit him every year. He even stood in as proxy for his father at Charles’ 1987 wedding. “My father is one of the most articulate, well-read, charming people I’ve ever known,” Harrelson told People in 1988. “Still, I’m just now gauging whether he merits my loyalty or friendship”.
Only time would tell.
Ron Galella, Ltd., Getty Images
17. He Funded His Father’s Defense
Harrelson continued defending his father—to the tune of millions. When Charles appealed his sentence and conviction, Harrelson was the one who ponied up the cash for the famed defense attorney Alan Dershowitz. A whopping $2 million later, however, Charles was no closer to freedom. Or, at least, that’s what Harrelson thought.
18. His Father Nearly Escaped
Woody Harrelson had spent a fortune trying to give his father a proper defense. Charles, however, wasn’t leaving his fate in the hands of his famous son. After his failed appeal, in July of 1995, Charles and two of his Atlanta Federal Penitentiary cellmates strung together an improvised rope and attempted to escape. They might have succeeded had a guard not fired a warning shot.
Harrelson had to find something else to dedicate himself to.
19. He Ditched Steak For Salad
In 2009’s Zombieland, Harrelson had to eat Twinkies made out of cornmeal and vegan substitutes. But he wasn’t just trying to be difficult. Decades earlier, Harrelson had adopted a strict vegan diet. “I was about 24 years old and I had tons of acne and mucus. I met some random girl on a bus who told me to quit dairy and all those symptoms would go away three days later. By God she was right”.
Meat was the next thing to go—and it clearly suited him.
Screenshot from Zombieland, Columbia Pictures (2009)
20. He Was PETA’s Pick
With or without meat, Woody Harrelson was a beefy hunk—one that every woman wanted to take a bite out of. In 2012, PETA named Harrelson the most irresistibly juicy vegetarian, right alongside the equally sizzling Jessica Chastain. Funny enough, that was the same year that Harrelson snagged another Emmy nomination. His love of plants, however, was a little too intense.
21. He Sowed The Seeds
When Harrelson discovered that the state of Kentucky didn’t differentiate between hemp for industrial use and marijuana for recreational use, he took action. Flanked by his lawyer (and CNN cameras), Harrelson planted hemp seeds. Needless to say, the stunt landed him in cuffs. And even more needless to say, that didn’t slow Harrelson’s activism in the slightest.
22. He Took Over The Golden Gate Bridge
Woody Harrelson kicked his activism up a notch later that same year. In order to protest a logging operation, Harrelson and a cabal of other activists took over the Golden Gate Bridge, climbed it, and then unfurled a banner. The stunt drew attention—and ire. Ultimately, Harrelson and his friends racked up charges ranging from trespassing to public nuisance.
He regretted nothing.
23. He Was A Tree-Hugger
Despite the charges, Harrelson was proud of his actions. “I shamelessly and proudly call myself a tree-hugger,” he explained. “When a tree gets to be 1,000 years old…wouldn’t you stop and think that maybe they’re more sacred than money?” But if there was anything that could get him down off that bridge, it was the opportunity for the role of a lifetime.
24. He Played Another Famous Outlaw
Harrelson’s next big role landed him in court. Playing the publisher Larry Flynt in 1996’s The People vs Larry Flynt netted the actor his first-ever Academy Award nomination, for Best Actor. But the actual hardware came a decade later, when he shared the 2008 SAG Award for Outstanding Cast for the Coen brothers’ No Country for Old Men.
Off screen, he was picking fights with a very different sort of opponent.
Columbia Pictures, Getty Images
25. He Faced The World Champion
When he wasn’t planting hemp seeds, scaling bridges, or snagging another golden statuette, Woody Harrelson was sitting down to a good game of chess. Against world champion Garry Kasparov, no less. In the summer of 1999, Harrelson—with the help of grandmaster Yasser Seirawan—managed to get a draw against Kasparov.
Harrelson’s real opponent, however, was still waiting for him in Kentucky.
Gage Skidmore from Peoria, AZ, United States of America, Wikimedia Commons
26. He Won In 25 Minutes
Harrelson’s hemp seed planting stunt had landed him in hot water: a misdemeanor charge for possession, a $500 fine, and the very real prospect of a year behind bars. As he waited for the courts to settle his case, he narrated Grass, a 1999 documentary on how the US came to outlaw the plant in the first place. And the documentary did its job.
On August 24, 2000, a Kentucky jury took just 25 minutes to clear him of the charges. The verdict knocked him sideways.
27. He Was Terrified Of The Clink
For all of his swagger throughout the case, Woody Harrelson had been terrified. “When they said, ‘Not guilty,’ I actually cried a little bit,” he admitted afterward. “I was afraid. There was a very real possibility of going to [the lockup]”. The jurors put him at ease on their way out, telling him nobody in that room believed a man should do time over industrial hemp.
Two years later, in London, he wouldn’t be so lucky.
28. He Led A Chase Through Piccadilly
In June of 2002, Harrelson was involved in a chase around London’s Piccadilly that one cab driver described as “something out of Hollywood”. For unknown reasons, Harrelson allegedly damaged the inside of a cab before skipping out on the fare, hopping into another cab, and then finally leading London’s finest on a foot chase.
After he paid a nearly $1,000 fine, the authorities dropped the charges. Harrelson quickly made his money back.
29. He Turned His Frenzy Into Film
The charges against Woody Harrelson disappeared when he paid his fine—but the story didn’t. On January 19, 2017, Harrelson turned his London escapade into Lost in London—one unbroken 100-minute take, beamed live into more than 550 US cinemas while the cameras rolled. For his self-directed masterpiece, Harrelson called in the likes of Owen Wilson and Willie Nelson.
The first-of-its-kind film project was a success, but he wasn’t loving every moment in front of the camera. Especially if it wasn’t his camera.
30. He Blamed It On Zombies
Harrelson has offered some wacky explanations for his more eccentric behavior over the years, but in 2006 he came out with a truly wild excuse. TMZ photographer Josh Levine went after Harrelson for $2.5 million, claiming that the Hollywood renegade had attacked him outside of a nightclub. But Harrelson had good reason: he had, he said, mistaken Levine for a zombie. Far-fetched as it sounded, it worked.
A judge tossed the case in 2010. By then, Harrelson had moved on.
Gilbert Carrasquillo, Getty Images
31. He Finally Married His Assistant
Two decades after Laura Louie turned up as his assistant on the set of Cheers, Harrelson was finally ready to actually clink glasses. The couple tied the knot in a December ceremony on the tropical island of Maui in 2008. But they skipped the Hollywood glare. The ceremony consisted of only the couple’s closest friends—you know, like Owen Wilson, Willie Nelson, Sean Penn, and Alanis Morissette.
By that time, Harrelson was already a family man.
32. He Had A Full House
Long before their wedding, Harrelson and Louie had been living like husband and wife. With three daughters, no less. Deni Montana came first, on March 5, 1994, followed by Zoe Giordano on September 22, 1996. Makani Ravello, the baby of the family, showed up on June 3, 2006, by which point her eldest sister was almost old enough to vote.
Suffice to say, his daughters saved his life.
33. His Daughters Keep Him Humble
If some Hollywood celebrities treat their kids like accessories to their fame, Harrelson is the exception to the rule. “My kids have always let me know what an idiot I am,” he explained. “They don’t pat me on the back unnecessarily. They’ve helped me to be a kinder, gentler soul”. Harrelson went so far as to say that parenting was “the best thing going”.
And it didn’t slow his career one bit.
34. He Earned Another Oscar Nod
If anything, fatherhood sharpened Harrelson’s on-screen talents. In 2009, he picked up his second Academy Award nomination—Best Supporting Actor this time—for his turn in The Messenger. That same year, he received another rare honor, though not for his acting. York University handed him an honorary degree for his tree-hugging instead.
His convictions ran deeper than the forests, though.
Andrew H. Walker, Getty Images
35. He Lost His Religion
Harrelson had been, by his own admission, “very religious” even into his university years. However, by 2009, all of that had changed. Sitting down with Playboy, Harrelson explained his journey away from faith: “I was getting into theology and studying the roots of the Bible, but then I started to discover the man-made nature of it”.
“My eyes opened to the reality of the Bible being just a document to control people”. And if there was anything he couldn’t stand, it was control.
36. He Called Himself An Anarchist
Harrelson’s break from control went beyond religion. “I’m an anarchist,” he said in 2013. And he wasn’t reaching for a punchline. Throughout his life, Harrelson has taken swings at occupants of the White House regardless of their party affiliation, disparaging the likes of Barack Obama and Richard Nixon in equal measure.
That kind of candor didn’t always work in his favor.
37. He Ruined His Own Interview
On February 3, 2012, Harrelson sat down for a Reddit “Ask Me Anything” segment. Ironically, he wasn’t actually interested in answering anything. To his fans’ frustration, Harrelson would only take questions about his new movie, Rampart. Reddit, being Reddit, did not take to being treated as a billboard particularly well, and the public backlash was palpable.
Not that it slowed his late-career surge any.
Jonathan Leibson, Getty Images
38. He Mentored The Girl On Fire
Harrelson wasn’t showing any signs of slowing down. Between 2012 and 2015, he appeared in cinemas as Haymitch Abernathy, the hard-living mentor who keeps Katniss Everdeen alive across The Hunger Games films. At the same time, he was pulling off magic tricks in another hit franchise, Now You See Me, as Merritt McKinney.
Screenshot from The Hunger Games, Lionsgate(2012)
39. He Quit After Three Decades
Hemp seeds and activism aside, in May of 2016, Harrelson quit smoking the green after more than 30 years of steady use. Talking to CBS the following year, he explained that he had suffered a “weird reaction” that he later identified as adrenal exhaustion. Harrelson also cooled off on the drinks, explaining that he wanted “to be emotionally available to my family, to my friends”.
Harrelson, however, was never a quitter.
40. He Fell Off The Wagon
Harrelson’s sobriety was going well right up until Willie Nelson entered the picture. The two sat down at the same poker table and Nelson handed Harrelson a big, fat doobie after the True Detective star scored a big hand. “I just grab it and I take a big toke,” Harrelson said, “and he [Nelson] goes, ‘Welcome home, son!’”
Sobriety or not, Harrelson was still at the top of his game.
41. He Got A Third Oscar Nod
In his mid-50s, Harrelson hit the best form of his career. His small-town chief Bill Willoughby in 2017’s Three Billboards Outside Ebbing, Missouri brought him a third Academy Award nomination while the entire cast walked off with the SAG Award. Still, three nominations and no statuette—though by then nobody in Hollywood was counting.
He was working on improving his chess record.
42. He Needed Three Takes
At the 2018 World Chess Championship in London, Harrelson had exactly one thing to do: make the ceremonial first move. Instead he toppled challenger Fabiano Caruana’s king, which in chess is how a player resigns. For his second attempt, he pushed the wrong piece. Like generous directors, the tournament officials granted him a third go, and he grinned his way through it.
His other hosting engagements were equally contentious.
Frans Peeters from Roosendaal, The Netherlands, Wikimedia Commons
43. He Hosted And Horrified
When Harrelson hosted Saturday Night Live in February 2023, he took aim at the COVID-19 pandemic response and divided audiences. “The biggest [cartels] in the world get together and buy up all the media and all the politicians and force all the people in the world to stay locked in their homes,” he explained. “I threw the script away. I mean, who was going to believe that crazy idea?”
Elon Musk approved of the joke. Producer Lee Goldberg decried it as “insipid”. Harrelson just did his thing.
Screenshot from Saturday Night Live, NBCUniversal (1975-)
44. He Opened A Dispensary
Off-screen, Harrelson has a knack for starting businesses. First, there was O2, an oxygen bar. But when that closed up, he gave customers something else to inhale. Starting in May of 2022, Harrelson opened the Woods WeHo shop, selling a lot more than hemp seeds. Shortly after that, a plant-based drinks business followed.
Holistic living had become his new thing. And another dark family secret may have had something to do with it.
45. He Had Chemistry With McConaughey
Back when Harrelson teamed with fellow Texan Matthew McConaughey in HBO’s True Detective, fans got to work on a mystery of their own: why did Harrelson and McConaughey look so alike? Harrelson and McConaughey worked so well together on screen that Emmy voters handed Harrelson another nomination. Their chemistry was too good to be a coincidence.
Screenshot from True Detective, HBO (2014–2024)
46. He Learned A Family Secret
The Harrelson-McConaughey resemblance remained a fun coincidence until 2023. Appearing on Kelly Ripa’s podcast, McConaughey spilled the beans. “In Greece a few years ago,” McConaughey reminisced, “We’re sitting around talking about how close we are and our families. And my mom is there, and she says, ‘Woody, I knew your dad’”.
And by “knew”, she didn’t mean it as a passing acquaintance.
47. He Did The Math
Continuing on Ripa’s podcast, McConaughey said he and Harrelson started to put two and two together. “We went on to unpack what this ‘knew’ meant and did some math and found out that his dad was on furlough at the same time that my mom and dad were in their second divorce”. Harrelson himself later confirmed McConaughey’s account.
But the truth was not something that everyone wanted to have come out.
48. His Maybe-Brother Doesn’t Want To Know
For Harrelson, a DNA test would settle the matter—and for the better. “You’re gaining a different father and a brother,” Harrelson explained of the possible DNA match. On the other hand (or side of the family tree), McConaughey remains more reluctant. “You’re telling me my dad may not be my dad of 53 years…I got a little more skin in the game”.
The test itself could wait.
Jose Perez/Bauer-Griffin, Getty Images
49. He Still Doesn’t Know
Years after the possible connection surfaced, Harrelson’s and McConaughey’s cheeks remain unswabbed. But a DNA test can’t tell them what they already feel to be true in their hearts. In a 2025 radio interview, Harrelson said, “Well, we haven’t done the DNA test, but we’re probably going to do that. I think there’s a real possibility”.
In the meantime, their children call each other “uncle”.
Kristina Bumphrey, Getty Images
50. He Got Off The Hamster Wheel
Harrelson now spends his time kicking back in Maui. Getting “off the hamster wheel,” as he calls it, did what no role ever could. He spends his time doing yoga and practicing Brazilian jiu-jitsu. “I’m feeling much more positive about my life,” he said, reflecting on the latest chapter in his ongoing saga. Not bad for the son of a hitman.
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Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28
