When Woody Harrelson was a kid, his father was just a normal dad. But by the time he grew up, Charles Harrelson was a twice-incarcerated hitman.

Sometimes, the most interesting actors come from eccentric parents or broken childhoods. The latter is certainly the case with Woody Harrelson, whose father was a professional hitman who spent most of his life in prison.

Charles Harrelson disappeared from Woody’s life in 1968 when the actor was just seven years old. Afterward, the elder Harrelson killed a Texas grain dealer and received a 15-year sentence. Somehow, Harrelson got out early for good behavior. That was in 1978.

The hitman’s freedom didn’t last long.

Charles Harrelson’s Biggest Crime

Texas drug lord Jimmy Chagra hired Harrelson to kill someone who stood in his way. Chagra forked over $250,000 because he faced a life sentence for drug smuggling. Chagra was scheduled to go before U.S. District Judge John H. Wood Jr. in El Paso, Texas, in July of 1979.

Defense attorneys nicknamed Wood “Maximum John” because of the harsh life sentences he handed down to drug dealers. The judge’s reputation proved to be his tragic undoing.

A single assassin’s bullet to the small of Wood’s back on May 29, 1979, felled the tough-as-nails judge.

The murderer used a high-powered rifle and a scope to kill Wood outside of his home in San Antonio as the judge went to get into his car. It was the first time in American history a sitting federal judge was assassinated.

An intense manhunt ensued, and the FBI finally caught Charles Harrelson and arrested him for murder.

Woody Harrelson had no idea about his father’s checkered occupation until he was listening to the radio one day. The actor heard a radio news broadcast discuss the murder trial of Charles V. Harrelson. Curiosity got the better of the young man, and he asked his mother if the elder Harrelson was any relation.

His mother confirmed that the man on trial for murdering a federal judge was indeed Woody’s father.

Reconnecting With His Son

A judge handed down two life sentences to Charles Harrelson in 1981. Even though the two were estranged, the actor said he tried to have a relationship with his father beginning the early 1980s. Rather than see the convicted assassin as a father, Harrelson saw his elder as someone he could befriend.

Even more astonishing, the Hollywood A-lister said he easily spent $2 million (yes, that’s million) in legal fees trying to get his father a new trial.

Chagra, the drug lord, was acquitted of conspiracy charges in connection with the assassination. He supposedly entered the witness protection program for helping the feds on other drug cases. It helped that Chagra’s brother was a defense attorney who made a lot of money. The theory was that if Chagra himself was innocent, shouldn’t Harrelson also be not guilty of murder?

A judge didn’t agree with Harrelson’s lawyers and the elder Harrelson spent the rest of his days behind bars.

At one point during his life sentences, the elder Harrelson made the audacious claim that he assassinated John F. Kennedy. No one believed him and he later recanted, explaining that the confession was “an effort to elongate my life.”

However, Lois Gibson, a well-known forensic artist, identified Harrelson as one of the “three tramps,” who were three mysterious men photographed shortly after the JFK assassination. Their involvement in JFK’s death has often been linked to conspiracies theories.

Charles Harrelson died of a heart attack in prison in 2007.

When asked if the convicted assassin influenced his life, the younger Harrelson said:

“Quite a bit. I was born on his birthday. 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. It was just mind-blowing to see all the things he did just like me.”

Harrelson’s quirky roles in movies certainly bespeak an interesting past. Just look at Natural Born Killers, Zombieland and Seven Psychopaths.

In the end, Woody said he and his father got along despite his time in prison for being the first person in history to assassinate a U.S. federal judge.

After learning about Woddy Harrelson’s dad, Charles Harrelson, check out Abe Reles, the hitman who mysteriously died in police custody. Then, read about Susan Kuhnhausen, the woman who had a hitman set on her, so she killed him.