Woody Harrelson: Contract Killers, JFK Conspiracies, and Fathers & Sons

One of Hollywood’s most eclectic and unpredictable actors, Woody Harrelson has played a hayseed barback, a streetball hustler, a natural born killer, a true detective, and so many more. But his most profound and difficult role might be his real-life role: the son of an infamous contract killer. Woody’s father, Charles Harrelson, was sent to prison for the assassination of a federal judge, only after he had been the subject of one of the largest federal manhunts in U. S. history – a manhunt that ended with a six-hour standoff with authorities during which he confessed to the assassination of JFK. This episode contains themes that may be disturbing to some listeners, including domestic violence. What's your take on the JFK assassination? Who do you think was behind one of the most infamous murders in history? Let Jake know at 617-906-6638, [email protected] mailto:[email protected], or on socials @disgracelandpod. To listen to Disgraceland ad free and get access to a monthly exclusive episode, weekly bonus content and more, become a Disgraceland All Access member at disgracelandpod.com/membership https://disgracelandpod.com/membership. Sign up for our newsletter and get the inside dirt on events, merch and other awesomeness - GET THE NEWSLETTER https://mailchi.mp/doubleelvis/disgraceland-email-newsletter Follow Jake and DISGRACELAND: Instagram https://www.instagram.com/disgracelandpod/ YouTube https://www.youtube.com/@disgracelandpod X https://twitter.com/disgracelandpod (formerly Twitter) Facebook Fan Group https://www.facebook.com/groups/491024204626127/ TikTok https://tiktok.com/disgracelandpod Check out Kikoff: https://getkikoff.com/DISGRACELAND To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices See omnystudio.com/listener https://omnystudio.com/listener for privacy information.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Speaker 00

  This is exactly right.

• 0:13Speaker 01

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• 0:42Speaker 02

  This is Iris Palmer from Against All Odds with Iris Palmer. You know it's the holidays when somebody in the family starts cooking before the sun comes up. The babusas are grilling in the pan, everybody's sneaking bites, and somehow, there's always room for one more person at the table. And nothing goes better with that first holiday plate than a delicious Coca-Cola. That crisp, refreshing taste makes everything that much better. Because the best holiday traditions aren't just about what we're eating, they're about who we're sharing those moments with. So check that shopping list twice. Stock up on Coca-Cola for all your family fiestas y disfrutas. Coca-Cola.

• 1:19Speaker 03

  This episode contains content that may be disturbing to some listeners. Please check the show notes for more information.

• 1:26Jake Brennan?

  Disgrace Land is a production of Double Elvis.

• 1:41Jake Brennan?

  This is the story of a killer, a contract killer. Perhaps a killer who is part of one of the most infamous murders of all time. But it's also the story about that killer's son. An actor, Woody Harrelson. An actor who made great films and great television. An actor who was and is inspired by great music. Unlike that music I played for you at the top of the show. That wasn't great music. That was a preset loop from my Mellotron called Texas Book Colonoscopy MK1. I played you that loop because I can't afford the rights to "Hot Stuff" by Donna Summer.

• 2:25Jake Brennan?

  And why would I play you that specific slice of Somerville Girl Cheese? Could I afford it? Because that was the number one song in America on May 29, 1979. And that was the day that Judge John H. Wood was gunned down in his driveway. An event that led to a manhunt, a questionable conviction, and a major shift in the way that Woody Harrelson would look at his father forever. On this episode, contract killers, assassinations, fathers and sons, and Woody Harrelson. I'm Jake Brennan, and this is DisgraceLand.

• 3:36Jake Brennan?

  April 1968, Houston, Texas. A red Cadillac convertible idled on the side of a desolate road, blanketed in darkness. Sandra Sue sat in the driver's seat. She was afraid of what Chuck was going to do to her when he got back. Chuck was outside, behind the Cadillac, with the man they'd picked up near the Brass Jug Bar. She heard muffled voices over the purr of the engine. Chuck was probably beating the piss out of the poor guy. Sandra Sue put a hand to the spot where Chuck hit her just minutes earlier when she got the car stuck in the mud. Chuck called her a stupid bitch and slapped her across the face. And it stung like hell. It wasn't the first time he hit her, and she knew it wouldn't be the last.

• 4:22Jake Brennan?

  Sandra Sue and Chuck hadn't been together that long. A few months, half a year maybe. She met him at a party. Six foot three, handsome. His eyes were a cavernous blue, impossibly big. They moved in together two days after their first date. At first, he was sweet, but his mood swung hard. He was violent. Only a few months into the relationship, she contemplated leaving him. But she was worried how he'd react. She didn't want to take any chances. Chuck, on the other hand, took chances all the time. He liked to gamble, though he wasn't very good at it. On a recent trip to Vegas, Chuck won and lost five grand in quick succession, which was not good because Chuck needed money, bad.

• 5:07Jake Brennan?

  Life or death bad. He didn't tell Sandra Sue that he had debts. Debts to people that you didn't want to be in debt to. He also didn't tell Sandra Sue that he was married, that he had three sons from an earlier marriage, or that he had been arrested for everything from drunk driving to armed robbery. Or that he carried around business cards that advertised his under-the-table services. Cards that read wars fought, revolutions started, assassinations plotted, governments run, uprisings quelled, women seduced, tigers tamed, bars emptied, orgies organized. Sandra Sue did have her suspicions. One night, after Chuck had taken out his anger on her yet again, she asked him, "Do you hurt people for a living?"

• 5:51Jake Brennan?

  Chuck's response? "Of course." On this night, Chuck pulled Sandra Sue into his world for the first time. He needed her help. He said that a carpet salesman named Alan Berg had cheated a man out of some money, and that Chuck had been hired to convince Alan Berg to pay it back. Chuck would get $1,500 for his assistance. So Chuck and Sandra Sue call Alan, tell him that she had seen him around town, thought he was cute and asked if he wanted to meet her down at the brass jug. She seductively told him what she'd do to him with her mouth when they met up. Alan Berg couldn't say no. Alan Berg also couldn't say no to getting inside the Cadillac when it pulled up hastily outside the brass jug where he was waiting like a rube.

• 6:35Jake Brennan?

  He couldn't say no because Chuck jumped from the vehicle before it even came to a screeching halt and shoved a 25 caliber pistol in Alan's face. "Get in the back," Chuck told him. Chuck got in next to him and then told Sandra Sue to drive. She floored him. Chuck tied Alan's hands in front of his body. And then he had Sandra Sue pull the car over on the outskirts of Houston when he took Alan out of the car and around the back by the trunk. And now Sandra Sue waited. She was nervous. She was shaking. She figured that Chuck's pistol was just for show. A tactic he used to convince these deadbeats to pay what was owed to the people who hired Chuck. Chuck was a scary motherfucker when he wanted to be.

• 7:18Jake Brennan?

  So it probably wouldn't take much time to convince Alan.

• 7:23Jake Brennan?

  Sandra Sue's heart leapt to her throat. She could hardly breathe. She stepped out of the Cadillac and ran back to the trunk. Chuck's pistol was smoking. Alan was face down on the ground. And there was blood all over Chuck's shirt. Sandra Sue's entire body shook. Chuck lifted the pistol and aimed it at her. Get back in the car. I swear to Christ I'll do the same to you. Sandra Sue hadn't signed up for kidnapping or murder. But she knew exactly what would happen if she didn't follow Chuck's instructions. As she got back in the caddy, she watched as Chuck dragged Alan's lifeless body off the road and into the brush. He walked back to the caddy again and pulled a shovel from the trunk. And then he walked back to Alan's body. And after a few minutes, he hollered to Sandra Sue. He needed her again.

• 8:08Jake Brennan?

  Sandra Sue got out of the car and walked over to where Chuck was trying to dig into the ground. He had taken off his coat and tie. He brought the shovel down on the ground, but the dirt was like concrete. God damn it, this wasn't going to work. And Sandra Sue heard a wet, eerie sound coming from the ground. She looked down and something low, muffled, pitiful. It was Alan Berg. Gurgling noises were coming from his mouth. She asked Chuck what was happening. Chuck looked down at the man he thought he'd just killed. "God damn it," he said. "Now I'm gonna have to choke him." Sandra Sue felt like she was gonna be sick. Chuck handed her the shovel and told her to take it back to the car. He took the rope he had tied around Alan's hands and wound it around Alan's neck,

• 8:52Jake Brennan?

  cinched it up deathly tight, and then used it to drag Alan back to the car where he tossed the twice-killed body in the trunk.

• 9:02Jake Brennan?

  Chuck looked at Sandra Sue. "I'm driving," he said.

• 9:07Jake Brennan?

  The two sat in silence as Chuck drove the Cadillac south for miles to where there was water. And that would be the easiest way to dump the body. Fuck that shoveling shit. And they were far from Houston, probably Galveston. City lights receded in the distance. Chuck spotted a watery ditch. He pulled the car over, got out, dumped Alan's body in the water. Before he did, however, he pulled a watch off the body's wrist. Not because it was expensive, which it was, but because he needed it as proof that he had fulfilled the contract. And that contract was not to scare Alan Berg into paying his debt like he had told Sandra Sue. That contract was to kill Alan Berg. Chuck didn't give a fuck about another man's debts. He had his own debts to pay.

• 9:55Jake Brennan?

  Woody Harrelson was angry. They said he had stolen a purse. Bullshit. He'd done nothing of the sort. They had no proof. They were basing their accusations solely on his reputation. Sure, he'd gotten into trouble before. It was part of his charm. Woody was lovable, but he was also a bit of a scamp. But this is going too far. Not only was he accused of a crime he didn't commit, now they're attacking him, too. Berating him, hitting him. Woody clenched his fists, he grit his teeth, he ran from the room where he was being pummeled and persecuted into another room in the building. And the anger just continued to build inside him. He felt like he was going to explode. His fists were white-knuckled instruments of vengeance. He just wanted to fucking hit something.

• 10:40Jake Brennan?

  So the first window he came to, he shattered. His balled-up fist went right through it, and he found another window and broke that one, too. But the building he was single-handedly destroying wasn't just any building. It was an elementary school.

• 10:55Jake Brennan?

  The person accusing him of theft and then beating on him was a teacher. Woody Harrelson was just a first grader.

• 11:04Jake Brennan?

  It wasn't the first time Woody's tantrums got him expelled from school. The first time was a few years earlier, in nursery school. As a kid, Woody was quick to anger. His temper was just about the size of his home state and just about as hot, too. He was born in Midland, Texas, in 1961, to parents who were polar opposites. His mother Diane was a strict Presbyterian and a positive role model who instilled the old-fashioned values of treating others the way you would like to be treated. Woody's father, Charles, on the other hand, was a troublemaker. He always seemed to be in and out of a jam, in and out of trouble with the law, as far as Woody could remember. His parents split up when he was only five. His father was rarely around.

• 11:48Jake Brennan?

  As the years went on, the memories of Texas faded along with those of his absent dad. In 1968, Woody moved with his mother and two brothers to his mother's hometown of Lebanon, Ohio. He tried to be good, tried to keep his juvenile record from getting any more chequered than it already was. But he was his father's son after all, which meant there was an element of trouble that was simply coded into his DNA. He often wondered if he would ever see his father again. His mother was amazing, no doubt, doing the single parenting thing and all, but Woody couldn't help but think that maybe his attitude would be better if his dad were here. He also wondered what his dad was doing at this very moment, or why he was doing whatever

• 12:30Jake Brennan?

  he was doing, far removed from his own flesh and blood, as if Woody and his brothers didn't even exist. And thoughts like those made him really angry.

• 13:14Speaker 01

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• 13:31Jake Brennan?

  All right, guys, I got something really cool for y'all. Come cruise the Caribbean with yours truly and some other great podcasters as part of the Virgin Voyages True Crime Voyage. Yes, we are going on a cruise together, Discos, you, me, Zeth, and a whole ship full of true crime fans. Now, Zeth and I are going to be taping a live version of DisgraceLand, one of our after-party episodes, and there's going to be some other great podcasters doing the same thing. The folks from Wisecrack, you guys know about Wisecrack, 2026's Podcast of the Year, Ambi Award winner and iHeart Award winner for Best True Crime Podcast. Also, the folks from Exactly Right's Buried Bones will be on board doing their thing as well.

• 14:12Jake Brennan?

  So if you want a live true crime DisgraceLand experience and a party to go along with it, live podcast recordings, behind-the-scenes storytelling, exclusive meet and greets, and immersive programming on a one-of-a-kind voyage, well, then you're going to make your plans right now for the Virgin Voyages True Crime Voyage, happening March 20th, 2027. March 20th, 2027. That's right, we are departing from Miami on that day and sailing to Grand Turk and the Beach Club in Bimini. Come hang with me, Zeth, your fellow Discos and true crime fans, along with the hosts from Buried Bones and Wisecrack this coming March, March 20th, 2027.

• 14:53Jake Brennan?

  Head over to www.virginvoyages.com/trucrim to secure your spot. Chuck sat on the bed of a motel room with Sandra Sue by his side. The lights from the Houston Astrodome shone through the dirty window. It had been two days since Chuck murdered Alan Berg and dumped the body in a watery ditch out near Galveston. Two days. That's all it took for Chuck to blow through the money he'd been paid. All $1,500. And he didn't use a cent to pay off any of the debts that he owed, which meant he had yet to unfuck himself in the bad debts department. Once again, he needed cash, fast. Which meant, he needed another job. So he found one. One that didn't require any killing.

• 15:38Jake Brennan?

  Not that Chuck minded killing, but this one would be easy, or so he thought. There was a knock at the motel room door. In walked Pete Scamardo, a Texas grain broker. Chuck didn't know what the fuck a grain broker was, but he did know that it was essentially a front for Scamardo's other business: heroin. Scamardo handed Chuck a condom filled with Mexican smack. If Chuck could sell it, they'd split the profits. And there was plenty more where that came from. Chuck agreed. Could be a nice little cash cow. Weeks later, Chuck still had the same rubber filled with the same heroin. No one wanted it. Desperate, he called a contact in Kansas City, who convinced Chuck to bring the dope to the heart of America, where he could easily find a buyer.

• 16:23Jake Brennan?

  But Chuck found no buyers in Kansas City. In fact, the first person he talked to when he rolled into town was a cop. He was pulled over the minute he hit city limits. Someone sold him out. Cops even had a search warrant for his car. Twelve fucking hours from Houston to KC and this is what he got for it. Chuck stepped out of the car with the condom stuffed deep in his jeans pocket. But while the cops poked around the car, he waited for the right moment, pulled a condom out of his pocket and dropped it, unnoticed, down a sewer drain or on the curb. Didn't matter. The police found a sawed-off shotgun in the glove box and charged Chuck with a federal firearms violation. He did not pass go, did not collect money for selling junk. He went straight to jail.

• 17:08Jake Brennan?

  He posted bail that night, thanks to the same friend who summoned him to Kansas City in the first place. But he wasn't in the clear yet. Now, he had to go back to Houston and tell Pete Scamardo that he'd dropped the heroin in the sewer while the cops searched his car. Scamardo was beyond pissed. Thousands of dollars of Mexican heroin down the fucking drain, literally. Chuck owed him, big time. But Chuck didn't have any money. No matter. He had the ability to do the dirty work that others didn't have the stomach for. And Scamardo had something that would get Chuck's hands real fucking dirty.

• 17:46Jake Brennan?

  Pete Scamardo had a partner in the green business, Sam Degilia Jr. Scamardo wanted him gone. If Degilia was out of the picture, then the company would collect $100,000 in life insurance. Scamardo could use half of it to pay off the business loans and the other half, well, don't worry about what he'd do with the other half. Scamardo offered Chuck two grand to put a bullet in Degilia's head. Chuck left Sandra Sue back home this time, and Jerry Watkins, an ex-con just out of prison who Chuck had recently met, went along for the ride. And they drove way the fuck out to McAllen, Texas, so far south that they were practically in another country. Chuck told Jerry to wait in the car. He took his 25 caliber pistol from the glove box. He thought about the two grand.

• 18:31Jake Brennan?

  It wasn't enough. It was never enough. He could start to make a dent on some of the debts he owed. He just had to resist the urge this time. Don't piss it all away on poker or booze. Easier said than done. Suddenly Degilia appeared. It was dark, but Chuck could see him walking near a small shack, alone. Degilia could hardly make out Chuck as he made his quick approach, but he saw Chuck's eyes, big, blue like tidal pools that spun in the shadows and swallowed the real estate of Chuck's face. Chuck trained the pistol on Degilia. He motioned to the shack, inside, now. Chuck followed Degilia inside the little shack. He told Degilia to get on his knees. The grain broker was shaking from his head to his feet.

• 19:14Jake Brennan?

  He tried to beg for his life, but he just stuttered through spittle and panicked breaths. Chuck repeated the instruction. On your fucking knees, now. Degilia dropped to his knees with a thud, and the plywood dug into his skin. He looked up at Chuck, six foot three, towering over him. Even though the barrel of the pistol was inches from his face, all Degilia could see were Chuck's blue eyes lurking behind him. Those eyes hypnotized her. Degilia didn't even notice that Chuck had moved the pistol even closer to his face and had begun to squeeze the trigger. Inside the car, Jerry heard the gunshot. He turned the ignition. An I-RA caller argued politics with a competitive host on the AM radio.

• 19:57Jake Brennan?

  And seconds later Chuck emerged from the shack. He got back in the car. And what the fuck was Jerry listening to? Talk radio? Nah. It was a long drive back to Houston and this shit was gonna bore Chuck to tears. He told Jerry to drive and then grabbed the tuner with his fingers and changed the channel.

• 20:15Speaker 05

  Breaking news to report tonight out of Texas. Charles V. Harrelson has been found guilty for the 1968 murder of Samuel DeGallia Jr. He has been sentenced to 15 years in prison.

• 20:25Jake Brennan?

  Woody Harrelson turned the car radio up, leaned his head in toward the speaker. Did he just hear what he thought he heard? Charles V. Harrelson? Could it be? How many Charles V. Harrelsons were there in the world? Nah, it couldn't, it couldn't be. His father may have been a deadbeat to his family or just a faded memory to Woody, but he wasn't a killer, right? Woody looked out the window and searched the parking lot for his mom's friend, the one who had picked him up from school to bring him home. She had stopped to run an errand and left him alone in the car. Then the report on the radio amplified just how alone he felt. His stomach began to turn. He dug his fingers into his palms and made a fist. He knew something wasn't right. He knew, deep down, that something was horribly wrong.

• 21:08Jake Brennan?

  He didn't know if he should be sad or if he should be angry. And sometimes, he couldn't tell the difference between the two. It was 1973, Lebanon, Ohio. Woody Harrelson was 12 years old. It had been years since he'd heard from his father, let alone seen him. Regardless, he felt a connection, a son to a father. Maybe it wasn't actually there, but he felt it. He wanted to feel it. Could be wishful thinking. Woody and Charles were both born on the same day, July 23rd. Woody thought about how someone once told him that the Japanese had this belief that if a son was born on his father's birthday, he wasn't like his father. He was his father. Wild.

• 21:50Jake Brennan?

  To think, somewhere out there, there was a man who was just like him, only a little older. What if they were exactly alike? And if Charles V. Harrelson was, in fact, a convicted murderer? Then what did that say about Woody? His fist got tighter. He felt sick. He wasn't paying attention when the driver's side door opened. He jumped. His mother's friend got back in the car. She looked over at him, and Woody looked like he was in shock. She asked him what had happened, was he all right? Woody paused to collect his thoughts and then said, "What do you know about my father?"

• 22:28Speaker 05

  We'll be right back after this word, word, word.

• 22:34Speaker 06

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• 23:04Jake Brennan?

  All right, guys, I got something really cool for y'all. Come cruise the Caribbean with yours truly and some other great podcasters as part of the Virgin Voyages True Crime Voyage. Yes, we are going on a cruise together, Discos, you, me, Zeth, and a whole ship full of true crime fans. Now, Zeth and I are going to be taping a live version of DisgraceLand, one of our after-party episodes. And there's going to be some other great podcasters doing the same thing. The folks from WiseCrack, you guys know about WiseCrack, 2026's Podcast of the Year, Ambi Award winners, and iHeart Award winner for Best True Crime Podcast. Also, the folks from Exactly Right's Buried Bones will be on board doing their thing as well. So if you want a live true crime DisgraceLand experience

• 23:49Jake Brennan?

  and a party to go along with it, live podcast recordings, behind-the-scenes storytelling, exclusive meet-and-greets, and immersive programming on a one-of-a-kind voyage, well, then you're going to make your plans right now for the Virgin Voyages True Crime Voyage, happening March 20, 2027. March 20, 2027. That's right, we are departing from Miami on that day and sailing to Grand Turk and the Beach Club in Bimini. Come hang with me, Zeth, your fellow Discos and true crime fans, along with the hosts from Buried Bones and WiseCrack this coming March, March 20, 2027. Head over to www.virginvoyages.com/trucrim to secure your spot.

• 24:34Jake Brennan?

  The blessing and the curse of playing a memorable TV character over the course of many seasons and many years is that the character never leaves you. Just ask Peter Falk. He starred in amazing films by auteurs like John Cassavetes and Vim Venders, but to most, he'll always be Columbo. Tom Selleck will always be Magnum P.I., George Reeves, Christopher Reeve, Superman, both to the end. And after eight years playing a country bumpkin barback on Cheers, Woody Harrelson could have very easily been Woody Boyd the rest of his life. Instead, when the long-running NBC sitcom wound down in the early 1990s, Woody pursued film roles that aggressively played against type.

• 25:17Jake Brennan?

  He played a street hustler on a half-court next to Wesley Snipes in White Men Can't Jump. He let Robert Redford sleep with his wife for a million dollars in a decent proposal. And then, he obliterated any remaining trace of Woody Boyd with a chilling performance as a natural-born killer in Oliver Stone's controversial and hyper-violent 1994 film. It was a role that was as different from Woody Boyd as Kirstie Alley was from Shelley Long. "I thought he was sort of a psycho," Stone said at the time when asked about the left-field casting choice. "That's why I liked him: his eyes were kind of blue and blank." Woody Harrelson had his father's eyes, naturally, even if he had only had the opportunity to look into his father's eyes a handful of times in his entire life.

• 26:01Jake Brennan?

  Charles Harrelson was doing hard time. Not for the murder of carpet salesman Alan Berg, for which he was acquitted in 1970, and not for the murder of grain broker Sam DeGilia Jr., the one that Woody heard about on a car radio when he was a kid, for which Charles served five years of a 15-year sentence. They let him out in 1978 on account of good behavior. It only took a few years for Charles's behavior to go from good to bad again, and once again, he was behind bars. And this time, it looked like he was there to stay. The fate of Charles Harrelson weighed heavily on Woody Harrelson's mind in 1997 when he appeared on Barbara Walters' annual pre-Oscares television special.

• 26:42Jake Brennan?

  Woody was nominated that year for his first Academy Award for another type-breaking role. This one, as the real-life head honcho of Hustler magazine in The People vs. Larry Flynt. Woody was thinking of his father again because Barbara Walters had brought him up. "It's fairly well-known," Walters said, "if anybody's read anything about you or talked with you, that your father went off to prison, convicted of murder. And tell me how you feel today and what the story is today." Woody paused and took a deep breath. The last thing anyone wanted to discuss was how their father was a convicted murderer. It was a sensitive subject. And even though Charles Harrelson was who he was, a hitman, a non-presence in his

• 27:23Jake Brennan?

  family's life, Woody wasn't entirely convinced that he was guilty of his most recent crime. Like when Woody was in first grade and a teacher blamed him for theft just because he had that reputation. Woody struggled to find a way to collect his thoughts coherently. "Well, he is in prison right now for the killing of a federal judge, which, well, I don't think it was a fair trial, especially because the guy who supposedly hired my father to commit the murder was later acquitted on a retrial." Barbara Walters doubled down. "Woody, do you think your father is innocent?"

• 27:57Jake Brennan?

  "I'm not saying my father's a saint," Woody replied, "but I think he's innocent of that one." That one would be the 1979 assassination of federal Judge John H. Wood, a crime for which Charles Harrelson was now serving two life sentences. Seventeen years before Woody's interview with Barbara Walters in September of 1980, Charles was arrested after a six-hour standoff with police in Texas near the Mexican border. He was in a state of cocaine-induced paranoia. He thought the Corvette he was driving was bugged, so he pulled it over and shot it up. This caught the attention of the authorities, who had already pegged Charles as suspect numero uno in the murder of Judge Wood.

• 28:41Jake Brennan?

  The search for Charles lasted more than a year and cost upwards of $12 million, one of the largest federal manhunt's in history. The prosecution later claimed that Charles was paid $250,000 from a Texan drug lord facing a life sentence for drug smuggling to quietly get rid of the judge who had a reputation for harsh sentences. But when police found Charles on the side of the road, he was anything but quiet. He was ranting and raving. He was waving a gun around. He stuck the gun under his chin and threatened to blow his own brains out. And this went on for hours. And during that time, Charles admitted to committing murder, but not just the murder of a judge. Charles Harrelson also confessed to the assassination

• 29:25Jake Brennan?

  of President John F. Kennedy. Hold up. You heard that, right? Woody Harrelson's father, contract killer and the subject of a massive federal manhunt, called a coked-up audible during a six-hour standoff with police and admitted to killing JFK. After his arrest, the sober Charles offered an explanation. "At the same time I said I had killed the judge, I said I killed Kennedy, which might give you an idea as to the state of my mind at the time," Charles told a Dallas TV station. "It was an effort to elongate my life." But Charles's explanation didn't stop the elongation of conspiracy theories that sprouted up around his roadside confession. One theory that has gained traction over the years was that Charles was one of three tramps arrested for vagrancy

• 30:09Jake Brennan?

  near the Texas School Book Depository on November 22, 1963. The tramp theory gave truthers pause. Was Charles Harrelson actually present the day JFK was shot? Was he actually telling the truth during that police standoff? It wasn't the only crazy theory about Charles Harrelson's mysterious past. Back in 1997, Barbara Walters asked Woody Harrelson about his claim that his father was actually a CIA operative. Woody nodded his head. How did he know? Where was the proof? Woody smiled and his head went from a nod to a shake. "Nah, see, I shouldn't get into this right now," he said. "This is where we're gonna get into trouble."

• 30:52Jake Brennan?

  Woody Harrelson knew trouble. He was born on the same day as his troubled and troublesome father, after all, which meant they weren't simply alike. They were the same. But the trouble that Woody was facing wasn't the kind you can simply chalk up to being young and dumb. Not like that time when he was 20 years old, jaywalking with a friend stopped by a cop who wanted to see some ID. Woody had his license on him, but told the cop he didn't. Why? And why the fuck not? When the cop found out Woody was lying, he threw him up against a wall, and Woody wriggled free and bolted. Why? He didn't know why. It was just a reaction hardwired inside of him. Within minutes, he was surrounded, on the ground, knee to the throat, handcuffed. They tossed him in a paddy wagon, which he did sit in for a little while.

• 31:35Jake Brennan?

  But when the paddy wagon made a stop to pick up some drunk and disorderly kids and the back doors swung wide, Woody ran. The handcuffs kind of made it more fun, honestly, and he ran so hard, he thought his chest would explode. He heard the cops behind him gaining, their feet flat and loud, their voices even louder. And Woody didn't notice the car. It came from the right, out of nowhere, directly in his path. His body hit it with a smack. He felt the nose of the thing dent his ribs. His body rolled over the hood, and then he hit the pavement, head first. And as he figured out a way to use his cuffed hands to clutch his aching head and his bruised ribs, it seemed like a whole precinct stood over him. And the mace rained down and burned his skin. Nah, Woody was no longer 20. He was 36. He had grown-up troubles now.

• 32:19Jake Brennan?

  Like, how does a son reconcile with a father who was not only absent, but was objectively not a good person at all? And what do you do with all this anger you feel? The kind you've carried around with you since you were a little kid? You know better than to let it out, let it have a voice, but it's a part of you. And just who are you? And why do you feel like you have no control over the person you've become?

• 32:58Jake Brennan?

  In 1995, Charles Harrelson attempted to escape from the Atlanta Federal Penitentiary, where he was serving two life sentences for the assassination of Judge John H. Wood. He crafted a ladder out of rope and hoisted himself over a wall. A guard caught him in the middle of his great escape and fired off a warning shot. Charles put his hands in the air and surrendered to his fate. That fate was an immediate transfer to the United States Penitentiary Administrative Maximum Facility in Florence, Colorado, a supermax prison that was notoriously escape-proof. With no chance of busting out of a supermax joint, Charles instead found refuge in isolation. Besides, what the hell did he think he was gonna do on the outside?

• 33:41Jake Brennan?

  Kill again for money and then blow it all gambling? Again and then repeat the cycle until the debts he owed eventually got him killed? On the inside, he had no other debts to settle besides the one he was paying for with the remaining years of his life. He had no contracts left to carry out. "The silence is wonderful," he wrote in a letter to a friend. "Being left alone is great. Nobody bothers me."

• 34:07Jake Brennan?

  2002, London. Woody Harrelson just wanted some of that wonderful silence and to be left alone as he sat in the back of a taxi in Piccadilly Square. A few days earlier, he chose not to be alone. Big fucking mistake. He wound up in a compromising situation with three other women. A paparazzo sold a steamy photo of the encounter to a UK tabloid. Woody's lapse in judgment nearly cost him his relationship with his longtime girlfriend and soon-to-be-wife. She forgave him, but he knew he'd let her down. He'd let himself down. And what was he doing? Who the hell was he? Was he Woody Boyd? Blissfully unaware of the double entendres flying around him behind the bar of Cheers? The mezcal and popping psychopath from Natural Born Killers?

• 34:52Jake Brennan?

  The bowler with the prosthetic hand in Kingpin? Or was he a laid-back Texas boy who sang the praises of all things hemp and got high with Willie Nelson on his tour bus? And maybe he was all of those things, but he hoped he was also a good son. His mother told him he was. His entire life, she told him so. Even when he got himself kicked out of school. But he lacked the validation from his dad. And he couldn't even help his dad out, no matter how hard he tried. He did help in small ways, like when he served as a proxy for Charles in 1987 so that he could get remarried from behind bars. But his larger efforts failed. He spent millions of dollars trying to get Charles a new trial. He even found a sympathetic judge.

• 35:35Jake Brennan?

  But after the judge and Woody were spotted playing a spur the moment game of pickup basketball, the judge removed himself over concern that the friendly match would be seen as biased. Everything fell apart after that, which sucked, because despite who Charles was and what he had done, there were things that didn't sit right with Woody about this conviction. The judge who presided over his original trial was allegedly a pallbearer at Judge Woods's funeral. Talk about bias. It was also said that the recording on which Charles was fingered as the hired hitman was obtained illegally. Woody felt the backseat of the taxi get small. He told the cabbie to stop. He wanted a bail. And the cabbie told Woody to hang on. And they were in the middle of four lanes of traffic and he had to pull over to the side of the road first. Nah, Woody wanted out.

• 36:20Jake Brennan?

  Now. He tried to open the door, but it was locked, and the cabbie was yelling at him to hold on, and Woody yelled back. He tried the door handle again, still locked, and the interior of the taxi swallowed him. Woody's heart rate doubled. He kicked at the door, and the taxi swerved as the cabbie panicked. But Woody kicked the door again, and it buckled, and one more kick would do it. He thrust his foot forward again. The door swung open, and Woody jumped out into the bustle of a London night. The cabbie followed in hot pursuit, so much for being left alone. And Woody ran. He held another taxi and jumped in, and the taxi with the broken door was right behind him. Soon, other vehicles joined the chase. A police car, and then another, and another, and six London police cars in total, lights

• 37:05Jake Brennan?

  flashing and sirens wailing, the distinctly European siren sound so frustratingly foreign.

• 37:13Jake Brennan?

  Fifteen years later, in 2017, a decade after Charles Harrelson died of a heart attack while still in supermax lockup, Woody Harrelson used the true story of the night he led police on a chase and then spent in a London jail as the basis for a dark comedy called Lost in London. Turning the self-described worst night of his life into a cathartic film project was an exercise in learning who he had been in the past and who he wanted to become. Someone better than before. He could use the future to make up for the past and to make up for any past disgrace.

• 37:53Jake Brennan?

  I'm Jake Brennan and this is DisgraceLand.

• 38:11Jake Brennan?

  Alright, thanks for checking out this episode of DisgraceLand. I hope you guys dug it. This week's question of the week is, who do you think killed JFK? And why was it Woody's dad? If not, who was it? What are your conspiracy theories? I want to know. I don't care how outlandish they are. Hit me up. Let me know. 617-906-6638. Leave me a voicemail. Send me a text. We'll get into it in the after-party. Let me know. You can also reach me at @disgracelandpod as well on Instagram, X, and Facebook. Leave a review for the show on Apple Podcasts or Spotify and win some free merch. Alright, here comes some credits.

• 38:45Jake Brennan?

  DisgraceLand was created by yours truly and is produced in partnership with Double Elvis. Credits for this episode can be found on the show notes page at disgracelandpod.com. If you're listening as a DisgraceLand All-Access member, thank you for supporting the show. We really appreciate it. And if not, you can become a member right now by going to disgracelandpod.com/membership. Members can listen to every episode of DisgraceLand ad-free. Plus, you'll get one brand-new exclusive episode every month, weekly unscripted bonus episodes, special audio collections, and early access to merchandise and events. Visit disgracelandpod.com/membership for details. Rate and review the show and follow

• 39:26Jake Brennan?

  us on Instagram, TikTok, Twitter, and Facebook @disgracelandpod and on YouTube at youtube.com/atdisgracelandpod. Rock-a-rola.

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