All About Woody Harrelson’s Parents, Charles and Diane Harrelson

Woody Harrelson was raised by a single mother while his father, Charles Harrelson, was in and out of jail

Woody Harrelson’s parents were practically polar opposites.

The former Cheers star was the second son born to Diane Harrelson (née Oswald), a devoutly religious legal secretary, and Charles Harrelson, a professional hitman who died while serving a life sentence for killing a federal judge. Woody and his brothers, Jordan and Brett, were raised by their mother Diane in both Texas and Ohio — while their father, Charles, was in and out of prison and only communicated with his sons through infrequent letters.

“I don’t feel he was much of a father,” Woody told PEOPLE in 1988. “He took no valid part in my upbringing.”

Despite Charles’ absence in his son's lives — and the crimes he was accused of committing —The Hunger Games actor developed a relationship with his father as an adult. Woody would visit his father in prison, helped him pursue a new trial and even stood in as his proxy when Charles got married in 1987.

“This might sound odd to say about a convicted felon, but my father is one of the most articulate, well-read, charming people I’ve ever known,” Woody told PEOPLE about Charles in 1988.

He added, “I look at him as someone who could be a friend more than someone who was a father.”

And while the True Detective star grew up without a father figure, he was close with his mother, grandmother and great-grandmother — who all raised him and his two brothers.

“I have a big appreciation for mothers,” Woody told GQ in 2012. “To me mothers are un-f------ believable."

So who are Woody Harrelson’s parents? Here is everything to know about the Emmy Award-winning actor’s mother and father.

Charles and Diane wed in the 1950s

Woody’s parents had a whirlwind romance: Charles and Diane married on a whim in Houston while he was on leave from the Navy, per Texas Monthly.

Charles and Diane moved to Los Angeles in 1959, according to the Houston Chronicle, where he sold encyclopedias — and also began to dabble in crime. He was charged with robbery the same year, but served as a jailhouse "snitch" in exchange for five years probation, the Chronicle reported.

In 1960, the couple moved to Midland, Texas, where they welcomed their three sons: Jordan, Woody and Brett — all born within three years of each other.

Charles left Diane and his sons in 1968

When Woody was just 7 years old, his father abandoned their family. But even prior to that, Charles was not a present father or husband, due to his frequent brushes with the law.

“I think they separated when I was seven,” Woody recalled to The Guardian in 2012. “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.”

And though it was Charles who walked away from their family, Woody revealed that his mother was no longer in love with his father by that point either.

“She was well out of love with him,” he told The Guardian. “You know, I’ve got to give her credit because she never really soured us on him, she didn’t talk negative about him, never, ever. And she could have — he wasn’t the greatest husband. Or father.”

Diane raised Woody, Jordan and Brett as a single mom

After Charles left the family, Diane moved her three sons back to her hometown of Lebanon, Ohio — where she raised them as a single mother with the help of her mother and grandmother. As a result, Woody is a self-proclaimed “mama’s boy," he told Esquire, and grew up “more feminine,” he revealed to GQ in 2012.

“They were all very good women,” Woody told GQ about his mother, grandmother and great-grandmother. “All very kind hearted, good souls, so I think it really shaped me positively.”

Diane worked as a legal secretary to make ends meet for her three children. Though times were often tight, Woody has spoken positively about his childhood in Ohio.

“We were poor,” Woody told the Financial Times in 2018 about his upbringing. “But my mom always took care of us [and] we always had food. It was a lot to raise three kids on her own as a secretary but she did it and she sure did look after us.”

Charles was a convicted hitman

Before Woody was famous for his acting roles, his father Charles was infamous — as a professional hitman.

Charles’ first alleged murder-for-hire was in 1968 when a carpet seller named Frank DiMaria supposedly hired Charles to take out Alan Berg, a rival carpet salesman from Houston, The Telegraph reported. Charles was charged in the murder — and Woody only learned of his father’s arrest when he heard about it on the radio, according to Texas Monthly.

“How many Charles V. Harrelsons can there be?” Woody recalled asking himself, per Texas Monthly. “That has to be my father.”

While Charles was acquitted in the murder of Berg, he was not so lucky when it came to the murder-for-hire killing of Sam Degelia, a Texas grain dealer. Prosecutors alleged that Degelia’s business partner — who wanted the life insurance payout — had hired Charles to carry out the murder, per The Telegraph. His first trial ended with a deadlocked jury, but in 1973, he was retried, found guilty and sentenced to 15 years in prison. Charles only served five years of his sentence, however, and was released in 1978 for good behavior.

Shortly after he was paroled, Charles was linked to another murder — and this time, it was the killing of a federal judge. A Texas drug trafficker by the name of Jimmy Chagra allegedly paid Charles $250,000 to assassinate Judge John Wood in 1979, according to Texas Monthly. Judge Wood was about to preside over Chagra’s drug trial when Charles allegedly shot him in the back with a hunting rifle while he was checking a flat tire outside of his home.

After a massive FBI investigation, Charles was arrested for Wood’s murder in September 1980, The Telegraph reported. He was found guilty in September 1982 and sentenced to two life sentences.

Diane brought up her sons in a strict, religious household

Religion was an important part of Woody’s childhood — thanks to his mother Diane, who was a devout Presbyterian.

“I was very religious growing up. My mom still is. We went to church all the time, went to Bible study; we even did Bible study at my house,” Woody shared with GQ in 2012.

He continued, “I was in ... all the way, and so I remember doing my first sermon when I was 17, I was in high school.”

Woody was so dedicated to his faith that he studied theology at Hanover College, a small liberal arts college in Indiana, with the intention of becoming a minister.

“It was a Presbyterian college at the time, and I was there on a Presbyterian scholarship,” Woody recalled during a 2018 appearance on Jimmy Kimmel Live!.

Woody added, “I was actually considering being a minister and then I just kind of went a different way.”

And although Woody did not end up pursuing a career in ministry, his mother’s faith and morals continue to influence him to this day.

“I do feel she was a great influence on me and instilled a lot of good values — just the way you treat people, behaving honorably, which I don’t always do, but she was a great role model for that and still is,” he told The Guardian about his mother in 2018.

Woody spent “millions” trying to get his father a new trial

Though Charles was absent for Woody’s childhood, Woody spent many years of his adult life trying to get his father a new trial for the murder of Judge Wood. The endeavor was not only time-consuming, but also expensive, the actor revealed to The Guardian.

“I tried for years to get him out. To get him a new trial,” Woody said in 2012, before admitting he “spent a couple of million … easily” in legal fees.

At the time, Woody said he did so because he was “just being a son trying to help his dad” — but the True Detective star has also claimed that his father did not receive a fair trial.

“I think that it was not a fair trial ... I’m not saying my father’s a saint but I think he’s innocent of that,” Woody said in an interview with Barbara Walters in 1997.

Charles once attempted to escape from federal prison

In 1995, Charles and two other inmates attempted to escape federal prison in Atlanta by using a makeshift rope to climb over a wall, the Orlando Sentinel reported. Charles and the other inmates — two bank robbers — all surrendered, however, after a warning shot was fired from the guard tower.

Following the escape attempt, Charles was transferred to Supermax in Colorado, the highest-security federal prison in the U.S., according to the Los Angeles Times. Other notorious inmates at Supermax included Unabomber Theodore Kaczynski, Oklahoma City bombing co-conspirator Terry Nichols and Olympic Park bomber Eric Rudolph.

Charles died in prison in 2007

On March 15, 2007, Charles died of a heart attack. He was 68 years old.

Felicia Ponce, a spokesman for the Bureau of Prisons, said that Charles was found unresponsive in his cell at the Supermax federal prison in Colorado where he was serving two life sentences. An autopsy later revealed that he had severe coronary artery disease, according to the Los Angeles Times.

Woody was born on his father’s birthday

Woody and Charles share the same birthday — July 23 — but 23 years apart. (Charles was born in 1938, while Woody was born in 1961.) Although Charles was absent for the majority of Woody’s childhood, their shared birthday created a connection between the father and son.

“They have 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, and it’s so weird when I would sit and talk with him,” Woody told The Guardian in 2012. “It was just mind-blowing to see all the things he did just like me ... Idiosyncratic things. The way he laughed. The face, very similar.”

Though Charles was in prison, the two managed to form a relationship as adults. “We got along pretty good,” Woody told The Guardian about his late father. When you can’t hang out and go to a pub, you know what I mean, it’s hard.”

Woody credits his mother Diane with giving him his “energy”

While he may look like his father, Woody shares several notable qualities with his mother Diane — including a shared passion for the environment.

“She cares about the world and nature,” Woody, who was arrested in 1997 at an anti-logging protest and narrated the 2020 climate documentary Kiss the Ground, told GQ about his mother. “I think she’s invested a little bit of that in me. I really do care about the world and nature.”

Woody also revealed that his mother instilled her sense of “compassion” and her energy in him.

“She’s got a lot of energy and she really is always doing something,” he told GQ. “Now, I’m a lollygagger. I’ll lollygag ‘til the cows come home, but I also think she gave me her energy.”

He continued, “Like, I have a good work ethic even though I have a better play ethic.”

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