Woody Harrelson’s Childhood Was Anything but Common

When it comes to celebrity pasts and early lives, we hear from time to time about an early tragedy or an unconventional upbringing. It’s not uncommon that talented adults rise from tumultuous childhoods (just think of Ray Charles or Charlize Theron, to name a few). But in the case of Woody Harrelson, his childhood and family life were particularly unique.

Newspaper headline / Charles Harrelson at the age of 65 / Charles Harrelson / Woody Harrelson
Source: Getty Images

It’s not every day that you hear about an A-list actor whose father was a hitman. Harrelson’s father, Charles Voyde Harrelson, has some other labels attached to his name, such as assassin and (possible) JFK conspirator. So, what happened within the Harrelson family? And how did/does Woody deal with such a heavy branch in his family tree? Maybe his tendency to choose psychopath roles in his movies isn’t by chance…

When a Smile Speaks Volumes

Have any of you seen Rampart, Natural Born Killers, Seven Psychopaths, or even Zombieland? If you have, then you’ve seen Woody Harrelson nail his film roles as an insane police officer, a deranged killer, and a psychopath. Woody has a way of coming off as terrifying in such roles.

Woody Harrelson attends the premieres
Photo by Frazer Harrison/Getty Images

Even when he plays nice, like in Cheers as the dopey bartender, there’s something in his lopsided smile that kind of makes you wonder – and worry – about his sanity and your safety. In an interview with The Guardian, Woody was asked what “messed with his head more” – Rampart or Natural Born Killers? “I’d say this,” Woody began, “when I was doing Natural Born Killers, I was doing some weird s**t, too.”

“I Was the Sanest Guy in It”

When the interviewer told him that the movie freaked him out, Woody smiled his charming/unnerving smile and said, “Really, it’s a misunderstood romantic comedy… a dark comedy.” Let’s just recall for a second that Natural Born Killers featured some “Hollywood headcases,” like Robert Downey Jr., Tom Sizemore, Tommy Lee Jones, and Juliette Lewis.

Micky Knox, played by Woody Harrelson, is being interviewed in prison by Wayne Gale, played by Robert Downey Jr. in the film Natural Born Killers
Source: Moviestillsdb.com / Copyright: Warner Bros.

“I know, it was a mad little time. After we’d been working on it for a while, I felt I was the sanest guy in it,” Woody admitted. So, who took it the hardest? “Tom and Juliette went a little crazy,” Woody said. He went on to reveal that director Oliver Stone actually encouraged madness: “He needed to create that mayhem because that’s what was on the screen.”

(By the way, Oliver Stone was blamed for a series of copycat murders after the movie was released in 1994).

His Life Could Have Gone Down an Entirely Different Path

Woody is one of Hollywood’s more interesting actors. It’s not just the fringe roles he plays and the way he plays them; it’s his backstory. And his backstory involves a very unusual family history. The thing is Woody’s life could have gone down a whole other path. For instance, he could have easily ended up as a church minister.

Woody Harrelson posed for a photo with his hands in his pockets.
Photo by Aaron Rapoport/Corbis/Getty Images

Why? Because his mother, Diane Lou, is a religious Presbyterian, as was he through his childhood. In fact, he even saw it “a bit” as his calling. He studied theology and drama at university, which was when his belief system started to collapse.

He Mentions His Mom, His Brothers…

For the most part, Woody has remained quite private about his family life. He has mentioned his mother – and his love for her – and his two brothers, growing up in both Texas and Ohio, making it seem, more or less, like he had a regular childhood.

Woody Harrelson and Mother Dianne Harrelson at the Premiere of 'White Man Can't Jump'.
Photo by Ron Galella/Ron Galella Collection/Getty Images

There have been anecdotes here and there on the web, stating that Woody Harrelson’s father was a contract killer. Many people likely assume it is an urban myth. When asked how he got on with his father, the answer is usually simple: “Pretty good.” He added that his parents separated when he was young, so his father “was not around too much.”

Away and Back

Did his father end up in prison? “Yeaah,” he began; “Yes. That explains his absence.” This is when he typically expects the subject to change. But in this Guardian interview, it didn’t. Woody was prodded to elaborate on his father.

A mug shot of Charles Harrelson, Woody Harrelson’s father.
Source: Pinterest

“I think they separated when I was seven. But he was gone a lot before that, in prison. Away and back. Away and back. It wasn’t like he was there all the time prior to that.” The media frames his father as a “contract killer,” and Woody agreed that it was a “fair job summary” of his dad.

To Woody, He Was Dad

The life and crimes of Charles Harrelson are detailed in an investigative Spotify podcast called Son of a Hitman by journalist Jason Cavanagh. The podcast highlights conversations with witnesses, lawyers, the authorities, and relatives of Charles’ victims.

Charles Harrelson is exiting the back seat of a car in handcuffs.
Source: Reddit

As Cavanagh sees it, the man was a ruthless murderer-for-hire, an abuser, conman and debt collector. But for Woody, he was dad. And not just for Woody, but for his two brothers, Jordan and Brett. The three sons grew up largely without their father around as he was in and out of prison.

The Moment He Learned About His Father

The Harrelson boys didn’t believe that their father committed the crime for which he was given his life sentences (an assassination that we’ll get into soon). They had questions, though. Woody actually remembers quite vividly the moment he realized his dad was a criminal.

News people interview Charles Harrelson in a Harris County Jail visitor's room.
Photo by Bettmann/Getty Images

“I was 11 or 12 when I heard his name mentioned on a car radio,” Woody recalled. He described how he was in the car waiting for a woman who was picking him up from school (helping his mom out), and he was listening to the radio. What he heard was about his very father.

A Wild Realization

The radio “was talking about Charles V. Harrelson and his trial for murder and blah blah blah.” Woody recalled just sitting there, thinking, “There can’t be another Charles V. Harrelson.” He thought to himself, “That’s my dad!”

Convicted hitman Charles Harrelson being escorted into court.
Photo by Bettmann/Getty Images

“It was a wild realization,” Woody stated. When the woman got back in the car and saw the boy’s face, she understood that something was up. Woody remembers going home that day in shock and trying to talk to his mother about it. “But there was little to say – the truth was out there, on the radio and in the papers.”

His Mom Was Mum

Did Mrs. Harrelson know what her husband did for a living? Yes. As Woody put it, “she was pretty hip to all that.” Did she love him? No. Woody said that although his mother was “out of love with him,” she deserves credit since she never “soured” her boys on him.

Ted Danson, Woody Harrelson, and Dianne Harrelson pose for a photo.
Photo by Ron Galella/Ron Galella Collection/Getty Images

He explained that his mother never spoke negatively about him to Woody or his brothers, “never, ever.” And she easily could have. He was, after all, a criminal and unfit father and husband. But his mom stayed mum. Who exactly she was protecting isn’t as clear.

A Womanizer From Lovelady

Charles was born in 1938 and raised in Lovelady, Texas. He served in the Navy as a sonar man, working sporadically as a salesman and a dental equipment repairman (of all things). The man was also a professional gambler and a self-proclaimed “expert card mechanic.” (No, that’s not a typo).

Lovelady City Hall.
Source: Pinterest

Charles once said: “I could put any hand you want at any position you want it, by simply opening up a new deck of cards and shuffling them.” Cards weren’t the only thing he got his hands on. He was also a known womanizer. (How ironic that he was from a town called Lovelady…).

A Con Man With a Personality

One ex-girlfriend of his, Sandra Sue Attaway, described how she fell in love with him instantly. Then there was a Texas Ranger who called him “a con man with a personality.” Cavanagh (the podcast guy) noted that nearly everyone he spoke to said Charles “was incredibly smart and incredibly charming.”

Charles Harrelson is sitting in court.
Source: Pinterest

Harrelson was first tried in 1968 for the murder of Alan Berg, a carpet salesman from Houston. Why would Charles take out a carpet seller? Well, it was alleged that a rival carpet salesman, Frank DiMaria, had hired Charles to do it.

The Alan Berg Case

Attaway (the ex-girlfriend) testified against Charles while also claiming that she helped lure Berg to a bar, where Charles forced him into a car at gunpoint and shot him. Berg’s remains were found in a ditch six months later. The next morning, the front page of the newspaper featured a photo of a police officer holding Berg’s skull.

A photo of Alan Berg at a wedding.
Source: Facebook

Frank DiMaria, by the way, was found not guilty of any involvement in Berg’s murder. When researching for his podcast, Cavanagh tracked DiMaria down and spoke with him briefly on the phone. “I have nothing to say about that,” DiMaria stated. “Nothing at all.”

A Dangerous Underworld

“When I spoke to Frank DiMaria, I realized that I do need to be careful,” Cavanagh stated. He originally planned to just show up at DiMaria’s home, but Alan Berg’s brother warned the podcaster: “Do not go over there to try to talk to him. Just don’t do that.”

Charles Harrelson is getting out of a car in handcuffs.
Source: Reddit

Going into this project, Cavanagh knew he would be looking at different worlds that were potentially dangerous. The FBI, CIA, organized crime, Hollywood – there are a lot of worlds in which people have an interest in not giving the full picture.

He Snagged the Right Lawyer

These are the kind of people that, as Cavanagh learned, can make people “disappear.” Charles, like DiMaria, was found not guilty in Berg’s case, thanks to his celebrity defense lawyer Percy Foreman, who represented organized crime figures like James Earl Ray, who assassinated Martin Luther King.

Charles V. Harrelson moments after pleading not guilty in the murder of Houston carpet executive Alan Harry Berg, confers with Percy Foreman and other attorneys.
Source: Pinterest

He also represented Jack Ruby, who shot Lee Harvey Oswald. (One wild story has Charles smuggling weapons into Cuba with Ruby.) How Charles even managed to snag Foreman as his lawyer in the first place is something Cavanagh never figured out. Anyways, Charles got off this time, but his luck wasn’t going to last.

The Sam Degelia Case

Charles was tried again, but this time for the 1968 shooting of Texas grain dealer Sam Degelia. According to the prosecution, he was hired by Degelia’s business partner who wanted his life insurance payout. Degelia was found in a barn with gunshot wounds to the head.

A newspaper clipping about the murder of Sam Degelia.
Source: Newspapers.com

The trial ended up in a deadlocked jury. Charles had to wait for three years in jail for a retrial. According to one prison guard, Charles always had money and status while behind bars. He even paid off a guard to have, um, “relations” with an inmate’s sister.

Sentenced to 15; Served 5

The retrial in 1973 found Charles guilty, and on the way out of court, one juror was overheard whispering to the convict: “I’m sorry, that’s the best I could do.” He was sentenced to 15 years in prison. He served only five (good behavior).

Convicted killer Charles Harrelson sits in jail.
Photo by Bettmann/Getty Images

His good behavior inside wasn’t going to influence him on the outside, though. By 1981, he was tried again and ultimately given two life sentences for the assassination of district judge John H. Wood. It was, remarkably, the first murder of an American judge in the 20th century.

The Biggest FBI Investigation Outside of JFK

The assassination occurred on May 29, 1979, on the morning of Jamiel “Jimmy” Chagra’s trial. Chagra was a narcotics trafficker from El Paso, Texas, who made $100 million in the 1970s alone. According to the official version of events, Charles committed a sniper-style execution of the judge.

Newspaper headline about the assassination.
Source: Twitter

Wood had been checking a flat tire on his car outside his home when he was shot in the back. Because it was the first in the century, it became the biggest FBI investigation outside of the JFK assassination. Eventually, Texas Rangers tipped the FBI about Charles Harrelson being a potential suspect.

Hotel Confessionals

Charles was arrested in September 1980, when he was already a fugitive on weapons charges. The man was extremely strung out, and even wrote confessional notes while in his hotel room. He wrote that he organized a deal in which each of his three sons would be paid $100,000.

Charles Harrelson was looking over handwritten notes in court.
Source: Reddit

He also stipulated that he never killed anyone who “was undeserving.” One noted read: “Since death is certain I should only be credited with speeding up a natural process… My marker should read ‘He did his part for ZPG – zero population growth.’”

Where Hallucination Ends and Reality Begins

The drugs Charles was on caused him to hallucinate, and he was convinced that there were FBI agents surrounding his hotel. The thing is the FBI very likely were there. As Cavanagh points out in his podcast, “It’s hard to know where the hallucination ends, and reality begins for him.”

A selfie of Jason Cavanagh
Source: Facebook

Two days later, his paranoia came to fruition and what occurred was a manic six-hour standoff with the police, before he was finally arrested. It was September 1, 1980 when the police just outside of Vanhorn, Texas found themselves in an intense face-off with the fugitive.

A Six-Hour Standoff

Charles was in a truly manic state at the time. He was convinced that there was a bomb planted in the muffler of his car, which is why he pulled over on the side of the highway in the first place and started firing his gun, blowing his car tire to bits.

Charles Harrelson wears a solemn expression as he is taken from a Harris County courtroom by an unidentified deputy
Photo by Bettmann/Getty Images

Shirtless with cutoff jeans and gold chains dangling off his chest, Charles essentially held himself hostage. Among the many things he claimed was that he killed John F. Kennedy. And then he threatened to kill himself.

The “Maximum John” Case

Charles was later sentenced to two life sentences for shooting a federal judge named John H. Wood, aka “Maximum John,” since he was known for his tough sentences. Judge Wood was set to preside over the trial of Jimmy Chagra. But did Charles really do it?

A photo of US District Judge John Wood Jr.
Photo by Bettmann/Getty Images

Some questions are still hanging over his guilt, like how a witness testimony was made under hypnosis, for example. And if you ask his son, he says it wasn’t a fair trial. Woody clarified: “I‘m not saying my father’s a saint, but I think he’s innocent of that.”

From Recorded Conversations to Hypnosis

The trial began two years later, in September 1982, and it lasted over two months, with 94 witnesses involved. Evidence against Charles included recorded conversations between Chagra and Chagra’s brother Joe. There was also a rifle stock linked to a purchase made by Charles’ wife (Woody’s mother).

Jamiel “Jimmy” Chagra being escorted to court in handcuffs.
Source: Tumblr

One eyewitness even underwent hypnosis, which Cavanagh calls “questionable judgment” on the FBI’s part. These days, a hypnosis testimony would never be admissible in court. That very witness, Chris Lambros, spoke on the podcast and said, “admissibility was stretched to its absolute limits” in order to secure a conviction.

The Harrelson Sons Aren’t Convinced

Charles was given two life sentences. Chagra was acquitted of the murder but served 24 years anyways for drug trafficking. In the eye of the law, Charles was where he needed to be. But his sons weren’t as convinced of his guilt, despite knowing the nature of their father’s character and job.

Actor Brett Harrelson attends
Photo by Ron Galella, Ltd./Ron Galella Collection/Getty Images

Cavanagh said it was “a little challenging” telling the Harrelsons details about who their father really was. Brett was one of the brothers interviewed on the podcast, and he believes there’s an “irony” to his father’s final sentencing.

Did He Do It? Could He?

To Brett, the assassination of the judge could be the one murder that he didn’t commit. “I think he probably didn’t kill Judge Wood,” Brett began; “But I think the state had to find somebody and I think he would have been the easiest one to convict.”

Jordan Harrelson takes a selfie in a recording studio.
Source: Pinterest

Eldest brother Jordan is more resigned: “Do I believe he did it? Do I believe he could have done it?” Jordan’s answers to his own questions were “Yes. Yes.” As for our dear Woody, he admitted to having spent “a couple of million” trying to free his father.

“This Is Where We’re Going to Get Into Trouble”

“I tried for years to get him out. To get him a new trial,” Woody explained. When he gave a reason for why he tried so hard, he said he was “just being a son trying to help his dad.” Woody also believed his father was a secret CIA operative.

Woody Harrelson at an event.
Photo by Francois G. Durand/WireImage/Getty Images

But when he mentioned that he also said, “I shouldn’t get into this right now… This is where we’re going to get into trouble… I know it’s true.” It was 1981 when Woody heard his father was arrested for killing the judge, and it was then that he tried to get in touch with him, at the age of 20.

There’s a Thing in Japan…

In that Guardian interview, Woody was asked if he sees much of his father in him. “Quite a bit… I was born on his birthday.” Woody then explained that there’s a “thing” in Japan “where they say if you’re born on your father’s birthday, you’re not like your father, you are your father.”

Charles Harrelson is laughing and holding a large folder while in handcuffs.
Source: Twitter

He further explained how it would be “so weird” when they would sit and talk. “It was just mind-blowing to see all the things he did just like me.” What kind of things? “Idiosyncratic things. The way he laughed. The face, very similar.”

He Died in Prison

Charles Harrelson ended up dying in prison in 2007, at the age of 68 – in time for him and Woody to become friends but not to get him out. During his research, Cavanagh went back and forth on whether Charles really killed Maximum John.

Charles Harrelson at the age of 65 in prison.
Source: Reddit

“I think he did some terrible things over the course of his life,” Cavanagh said about Charles. “And I think he’s someone who lived by his own moral code and had a bizarre philosophy about the world and life. But there was actually a jailer who knew another side of Charles Harrelson.

The Conversations Between “Boss” and “Deacon”

Retired Deputy Jim Kershaw used to work the night shift at the Harris County Jail between 1980 and 1983. He had countless talks with many “guests” of the jail. And his talks with Charles Harrelson are some that he remembers to this day.

Deputy Jim Kershaw is standing next to a patrol car.
Source: Facebook

“We got along pretty good,” Kershaw said in a telephone interview. “We developed a good relationship, so much so that we had nicknames for each other.” Apparently, Charles called him “Boss” and he called Charles “Deacon.” Kershaw said he called him that because of his knowledge of the Bible.

He Was Well-Mannered and Intelligent

Charles would quote the Bible and “was one of the most well-mannered and intelligent people that I ever met in jail,” Kershaw claimed. At the time, Charles was serving time at the Harris County Jail for felony weapons possession (after the six-hour stand-off).

The inside of Charles Harrelson’s jail cell, with a tv, some books and a few newspapers.
Source: Reddit

It was what the guards referred to as “death row,” since it was a place where high-risk inmates were isolated from the other prisoners. Kershaw was only 21 at the time and in charge of keeping watch over these inmates, including Charles. His conversations and dealings with Charles are not those you would typically associate with a convicted killer.

Cool, Calm, and Collected

As Kershaw recalls, the inmate spoke more of his family than his criminal acts. Kershaw had limited information on the convicted murderer that he enjoyed talking to and had no idea he would ever be linked to what the FBI dubbed “the crime of the century.”

Charles Harrelson is led away from Federal Court 12/14 after a jury found him guilty in the murder of Federal Judge John H. Wood.
Photo by Bettmann/Getty Images

“We were told that he was a rumored hitman for organized crime,” Kershaw said. “He did look like a hitman. I mean nobody bothered him. I knew not to turn my back on him.” Charles was always cool, calm and collected. And he was a “great card player,” too, who happened to make his own playing cards.

They Butted Heads Only Once

Kershaw remembers that Charles didn’t have many visitors during the years he worked at the jail. It was mainly just his then-wife Jo Ann and his attorney. What the jailer noticed was that Charles was always writing letters.

Charle Harrelson dressed in his prison jumpsuit, looking annoyed.
Source: Tumblr

He had a large stack of papers in his cell at all times – it kept him busy. While the jailer and the “jailee” were cordial most of the time, there was one occasion where they butted heads. As Kershaw recalled, “Deacon” was on a hunger strike. Kershaw consistently put his food tray outside his cell, but this one time, he didn’t.

His So-Called Hunger Strike

Charles was angry because his tray wasn’t outside his cell this time. Kershaw knew that Charles was eating the food (his cell neighbor would push it over to him). He told Charles to run his hunger strike with the rest of the world, but not him.

Charles Harrelson being escorted by a cop and detectives while handcuffed.
Source: Reddit

“One minute it was like you were speaking to a CEO of a corporation and the next, I’d be talking to a con man. You just never knew who he was going to be.” In 1981, after being indicted for the murder of the judge, Charles was transferred to the Bexar County Jail in San Antonio.

Their Last Conversation

Kershaw said he’ll always remember what Charles told him before he left. In what would be their last conversation, “Deacon” told him, “No matter the road you take in life, always tell your family you love them.”

A photo of Charles Harrelson in a suit and tie.
Source: Twitter

Kershaw admitted to using that line on people since then. “As much as he was a convicted killer, I always believed he would have preferred just being a family man.” According to the book Dirty Dealings by San Antonio lawyer Alan Brown, Charles’ defense attorney, Woody came down to see his father numerous times. Brown said Woody wasn’t yet a star back then – “just a strange kid who didn’t say much.”

How Old Is Woody Harrelson?

Woody Harrelson is 59 years old, and it’s difficult to imagine that his character – both on and off-screen – hasn’t been shaped in one form or another by his father. Woody, despite his leftist views, makes a pretty convincing redneck when he plays those characters.

Woody Harrelson attends Giffoni Film Festival 2019.
Photo by Vittorio Zunino Celotto/Getty Images

But he said, while grinning his signature grin, that it wasn’t always like that. “I was a freshman in college in 1980, the year that Reagan was elected, and I went around badgering people to vote for him.” He explained that he was part of the Young Republicans and “bought all the bulls***.”

A Time of Excess

By his early 20s, Woody gave up on religion and Reagan. He got the part on Cheers and was introduced to environmental politics by his co-star Ted Danson. It was a time in Woody’s life that he was eating up everything around him.

Cheers star Woody Harrelson poses for a portrait.
Photo by Aaron Rapoport/Corbis/Getty Images

He admitted to going through a phase of “Satyricon. A time of definite excess,” which included numerous women. The way Woody sees it, “the road of excess leads to the palace of wisdom.” What’s both interesting and impressive is the fact that Woody has been with the same woman for three decades.

When Woody Met Laura

The two met in 1987, when Laura was his assistant. It took him some time, but he eventually realized he was in love with her. “I went to Africa, and I’m sitting around the fire out there, in Nairobi, thinking about her, fantasizing about her,” he described with a look of embarrassment on his face.

Laura Louie, Woody Harrelson arrives at the 90th Annual Academy Awards
Photo by Steve Granitz/WireImage/Getty Images

When he came back from Africa, he was too nervous to tell her. He recalled sitting there with a guitar, so he wrote a song for her. He ended up singing it to her. After he serenaded her, she told him, “Woody, I’ve been in love with you for the last two and a half years.”

They Moved to Hawaii, Thanks to Willie Nelson

“Then I picked her up and carried her in,” Woody recalled. He and Laura eventually tied the knot in 2008, after having already been together for years. The two have three daughters. The family moved to Hawaii – the 50th state that he only really knew because of country singer Willie Nelson.

Woody Harrelson is looking at a rainbow from the front porch of his house in Hawaii.
Source: Instagram/ @woodyharrelson

Woody saw Nelson play once, and after the show, Nelson’s wife Annie came up to Woody to tell him that Nelson wanted to hang out with him on the bus. After opening the bus door, and seeing through all the smoke, he sat down with the country singer.

The Good Life

“So, I go in and start hanging with Willie and I don’t know this is going to become one of my best buddies in life.” Nelson then invited Woody to visit him in his home in Hawaii. That’s when Woody and Laura discovered the remote part of Maui, and they never looked back.

Woody Harrelson and Willie Nelson backstage at Farm Aid.
Photo by Ebet Roberts/Redferns/Getty Images

For three years, Woody didn’t make a movie. He chose to take a hiatus and live the good life. He and Nelson would hang out on his porch, strumming away on a guitar, smoking “big fatties.” It was also a chance for Woody to write.

Chaos and Creativity Go Together

He wrote the play Bullet for Adolf, (with Frankie Hyman) which premiered in Toronto in 2003. It’s safe to say that Woody Harrelson has led a pretty remarkable life. And he knows it. “It’s quite a dichotomy,” he said, referring to his life.

Actors Lee Osorio, Marsha Stephanie Blake, Woody Harrelson, Nick Wyman and Shamika Cotton take a curtain call at the
Photo by Mike Coppola/Getty Images

He then recalled something a taxi driver once told him. The driver told Woody, “Chaos and creativity go together. If you lose one percent of your chaos, you lose your creativity.” Woody said it was “the most brilliant thing I’ve heard. I needed to hear that years ago.”