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- [00:00]
Kristen Bell
Foreign.
- [00:08]
Jake Brennan
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Quint works directly with top artisans to cut out the middlemen and give us luxury pieces without the markups. I've even turned my wife onto quint. Quint has 100% European linen shorts and dresses for $30, luxe swimwear, Italian leather plat sandals and so much more. And again, the best part, everything with Quince is half the cost of similar brands. Give your summer closet an upgrade with quints. Go to quints.com Disgraceland for free shipping on your order and 365 day returns. That's Q-U-I-N-C-E.com Disgraceland to get free shipping and 365 day returns. Quints.com Disgraceland Disgraceland is a production of Double Elvis. The stories about Waylon Jennings are insane. He gave up his seat on a plane hours before it crashed and killed, among others, Buddy Holly. He stashed his pills in the wall of his apartment to hide them from his pill head roommate, Johnny Cash. He did blow during halftime of an NFL game with the Oakland Raiders, pulled a loaded gun in the recording studio and was arrested by the DEA after a kilo of cocaine was sent to him in the mail. Waylon Jennings was a badass and a taker of no shit. A major player in the formative days of both rock and roll and outlaw country. And he made, of course, great music. Unlike that loop I played for you at the top of the show. That Wasn't great music. That was a preset loop from my melotron called John hughes fever dream mk2. I played you that loop because I can't afford the rights to Best of My Love by the Emotions. And why would I play you that specific slice of Whoa, whoa, cheese. Could I afford it? Because that was the number one song in America on August 24, 1977. And that was the day that federal agents raided a Nashville studio in the middle of a recording session with a warrant for Waylon Jennings arrest. On this episode, a plane crash, pill stashes, coked up Oakland Raiders, loaded guns, badasses, and Waylon Jennings. I'm Jake Brennan, and this is Disgraceland. You know when you have a great idea? Maybe you finally figured out what the meaning of life is? Or you've got this idea for a great recipe for a Thanksgiving dinner where you stuff a chicken inside of a duck that's stuffed inside of a turkey. Whatever, it doesn't matter. What matters is that you get this idea in your head. Something original, something unique, something genius. So genius that you're convinced that no one else has ever thought of it. But you want to make sure. And we live in a time where you can make sure with a few keystrokes. So you Google it, and guess what? Turns out you're no genius after all. Tens, hundreds, maybe thousands of people have already thought of that same brilliant idea. Some 70 years ago in the 1950s, there was no Google, so there was no quick way to confirm if your idea was unique to you or not. That said, I am confident that Elvis Presley wasn't the only person on the face of the planet at that time thinking about taking country music and the blues and mashing them together to create something new. He just happened to be the first one to put that thought into action. And that thought, breaking with tradition, breaking down color barriers, it was also on the minds of others, like 800 miles due west from Elvis, from Memphis, all the way over in West Texas. First in the small town of Littlefield and then Lubbock, where young Waylon Jennings was sharing that brilliant idea long before the Tupelo Kid told his band to get real gone. And just like Elvis, at least the Elvis before Colonel Tom Parker entered the picture. And just like many of the strong, humble folk out there in West Texas, Waylon Jennings didn't do what he didn't want to do. He didn't want to pick cotton no more. So he quit. He didn't like school, so he dropped out. What he did want was to sing and play guitar and also play records on air at KDAV, a small radio station in Lubbock, Texas, where 18 year old Waylon Jennings, newly married, worked as a DJ. Country, blues, R and B, he loved it all and he played it all. Especially Little Richard. Tutti Fruity sent his listeners into a frenzy, but not necessarily for the reason you'd think it was. Because this was supposed to be a country music radio show and here was Whelan spinning R and B. The station manager, Waylon's boss, was so pissed that he got into his car, drove all the way over to the station and tore Waylon a new one. But that didn't cramp Waylon's style. In fact, he doubled down the next night. He played Little Richard and Ray Charles back to back. And that same night he was fired. Didn't matter, because Waylon Jennings wasn't meant to play other people's records on the air. He was meant to make his own music. His good friend and fellow Lubbock resident Buddy Holly was convinced that Whelan was as talented as Texas was big. Which is why Buddy played guitar on Whelan's first single, Joe Lay Blown. And then in December of 1958, Buddy Holly, at the time one of rock and Roll's Pioneers, a 22 year old megastar, came to his friend Waylon Jennings, one year Buddy's Junior, and handed him a bass guitar. You got two weeks to learn that thing, Buddy told him, and I'll see you in New York for the tour. Tour, New York. The bass. Waylon didn't play bass. Not that it was all that different from his instrument of choice, guitar. But Buddy believed in him. Whelen was the guy for the job, end of story. He and another of Buddy's friends, Tommy Alsa, would be replacing Buddy's backing band, the Crickets, after they walked following a contract dispute. So Whelan got to learning Buddy's songs on a four string. Then he took a red eye from Texas to the big city where the rest of his life was there waiting for him. January 1959, Grand Central Station. Waylon Jennings and Buddy Holly squeezed themselves into a photo booth and dropped a coin in the slot. Whelen stuck a menthol cigarette in his mouth and lit it up. Buddy elbowed him. Waylon, gimme a Salem. Waylon passed one over and the camera began to flash. Both of them with huge grins on their faces. Waylon wearing dark shades, Buddy in his trademark horn rim glasses. To Waylon Jennings, Buddy Holly wasn't just a good friend. He was what he called an upper, as were the shows they were playing. Uppers. Ballrooms packed with teenagers dancing along to the Big Boppers singing Chantilly Lace, Ritchie Valens doing La Bamba, before finally pressing up tight against the stage. When Buddy closed out each night, the whole room feeding off that energy, Buddy Holly's energy. Waylon, for one, couldn't get enough of it. He was addicted. Buddy Holly was a drug. That drug empowered Waylon and the others through a grueling tour, night after night, city after city. Even in the Midwest, in February, in the dead of winter, 40 below at times, 40 below. The tour bus was a meat locker and everyone was getting sick. Buddy decided to rest up. During the next leg of the trip from Iowa to North Dakota, he chartered a plane. He offered the two extra seats to his band, to Waylon and Tommy also. But just hours before the flight, the Big Bopper, hit hard with the flu, asked Waylon if he would consider giving up his seat. Whelen could see that the Bopper and his current state needed a break from the bus more than he did. So Waylon gladly gave it up. And then Tommy also lost his seat to a last minute coin toss with Richie Valance. Word got to Buddy right before the plane took off. He found Waylon, and as all good friends do, really good friends anyways, he gave Waylon. You're not going with me tonight, huh? What, did you chicken out? It's not like that, Waylon told him the Big Bopper sick. And it seemed like the right thing to do. Do okay then, Buddy said, again with the talking. I hope your damn bus freezes up. Well, Whan responded, I hope your old plane crashes.
- [10:29]
News Anchor
We interrupt this program for a special news bulletin. Three young singers who soared to the heights of show business on the current rock and roll craze were killed today in the crash of a light plane in an Iowa snow flurry. The singers were identified as Richie Valen, 17, Buddy Holly, 22, and JP Richardson, known professionally as the Big Bopper. Their small chartered plane crashed in a lonely farmyard about 15 miles northwest of Mason City. Cause of the crash was due to inclement weather conditions. Details upcoming from Action Central news.
- [11:06]
Jake Brennan
Buddy Holly's death in 1959 at just 22 years old came as an incredible shock, not least to his good buddy, Waylon Jennings. Waylon was racked with guilt, convinced that his last words ever spoken to Buddy were the reason that he died. I hope your old plane crashes. That line, those words, they echoed in his head, a telltale heart beating from beneath the floorboard of the tour bus, which continued to rattle along through America. The show must go on. And go on it did, with a grieving Waylon Jennings made to perform as his dead friend for the next few shows before an impersonator was hired to play Buddy Holly. Let me, Let me repeat that. Buddy Holly had just died. And Waylon Jennings was made to perform posing as his dead friend Buddy Holly for the next few shows before a Buddy Holly impersonator was then hired. Waylon and Tommy Alsop were promised money and time off to fly to Buddy's funeral, but that never came to pass. A month later, Waylon returned to where he started with little to show for it back at Grand Central Station, this time not goofing off in a photo booth, but instead placing Buddy's bass and amplifier in a storage locker. He shut the door, locked it, and mailed the key key to Buddy's widow. Then he began the long drive back to West Texas from New York City, but without his upper his Buddy. So Waylon needed something else to help him make it through those long nights of White Line Fever. He managed to get by this time, not with a little help from his friends, but with some pills he caught from a truck driver at a rest stop and the sound of the grand ole opinion crackling out of the car's radio. So the convenience of being able to pay for almost everything these days, digitally, yeah, it's easy. But guys, I don't know about you, it's also very easy to lose track of what I'm spending my money on. Okay, I looked at my credit card statement a couple weeks ago and the amount of garbage I realized I was spending money on was staggering. I don't think I spend a lot of money on takeout food, but I do. I don't think I spend a lot of money on buying garbage that I don't need on a random Sunday afternoon walking through town with my family. But I do. Did I really need that Uber XL ride both to and from the airport? Probably didn't. I realized all this from using Monarch Money, which is an award winning budgeting app. Helps you not only manage your money, but like I said, for me, it helps me track what I'm spending on and identify where I can save. I use it weekly now every Saturday morning as part of my routine when I'm drinking my coffee, paying my bills, I track my weekly spending with my Monarch Money app. And I can do it by category. And because of this, I'm saving a ton of money now. Monarch money is the real deal. Over a million households are using it, not just the Brennan household. Wall Street Journal named it the best budgeting app of 2025 and it has over 30,000 five star reviews. Get control of your overall finances with Monarch Money. You use code disgraceland@monimalmoney.com in your browser for half off your first year. That's 50% of your first year at monarchmoney.com with code disgraceland. Hey Discos, if you want more Disgraceland, be sure to listen every Thursday to our weekly After Party Bonus episode where we dig deeper into the stories we tell in our full weekly episodes. In these After Party Bonus episodes, we dive into your voicemails and texts, emails and DMs and discuss your thoughts on the wild lives and behavior of the artists and entertainers that we're all obsessed with. So leave me a message at 617-906-6638, disgracelandpodmail.com or disgracelandpod on the socials and join the conversation every Thursday in our After Party Bonus episode. So one thing you probably don't know about me is that I just picked up golf and as you can likely assume, I am horrible at it. Okay? That said, I'm also loving it. And I don't care how annoying it is to be trapped behind me on the course. I might not be banging any holes in one anytime soon, but I am banging back. 5 hour energy transfusion Shots on the course. That's right. Inspired by the unofficial golf cocktail, this energy shot tastes great. Hints of grape, ginger, lemon and and and and it's all without alcohol, but with as much caffeine as a premium cup of coffee. So look, if you're playing behind me and I just missed my chip shot for like the fourth time a chill b know that I'm doing the best I can, man. I'm hitting that five Hour Energy transfusion to keep me going as fast as I can. And you should be doing the same. It's easy to stash your five Hour Energy anywhere in your bag, ready for your early morning tea time, a late round, whatever five Hour Energy is there to help you tee off. Five Hour Energy Transfusion flavor is available online or in stores. Head to www.fivehourenergy.com to order yours today. Waylon Jennings had been awake for days, clutching a fistful of pills while three different women waited for him in three different rooms on three different floors of the same hotel. They'd have to wait a little longer. Right now, Waylon had to listen to his longtime Drummer Richie Albright speak his mind, Waylon. Richie said, you're going to kill yourself. Waylon couldn't argue with that. He never knew when enough was enough. That went for pills and later, cocaine. That went for women. And that went for music, too. Waylon Jennings was also a man who didn't do what he didn't want to do. Not cotton picking, not school. He tried going back to the DJ booth, back to a normal life in Lubbock, Texas. But that upper, the Buddy Holly upper, the thrill of the road and of performing, he couldn't shake it. Buddy Holly was the gateway drug. And it didn't take long for Waylon's Cadillac to drive right through that gate over to the other side where those aforementioned pills were waiting. White crosses, speckled birds, Louisiana turnarounds. In some parts of the American South. One greets a stranger by asking, what y' all got in the smoker? In Nashville in the 1960s, it was, y' all got any pills? Pills were the gasoline in the Music City tank, a cultural currency second only to the music. Nashville even had a popular physician on call, Dr. Snap, who was wrote scripts on the regular above board, completely legal, because this was a time when pills were seen not so much as an addictive drug, but as a necessary medicine to do your job. And if that sounds naive, well, Waylon Jennings, like Johnny Cash and many others making their way in Nashville at this time, was little more than a naive kid from the country who didn't know any better. And also, like Johnny Cash, Waylon was a fiend for pills. So much so that when the two of them were roommates in Nashville, they had to keep their respective stashes hidden from each other. I'm gonna find those goddamn pills, hoss. Johnny Cash was inside Waylon's car, on his back up front on the floor, ripping apart the interior. He yanked the paneling down. Nothing. He knew they were here. What he didn't know is that they were here yesterday. Waylon never used the same hiding place twice. Stashing pills was a fluid game. This week, Waylon had unscrewed a light switch panel in the wall of their shared apartment and dumped a big bag of pills in the cavity. Boom. Cash was never gonna find him. Only problem was, when Waylon really needed them, he was gonna have to kick a hole in the drywall to get them out. But hold up. I'm getting ahead of myself. Let's back up. Before Nashville and after Buddy Holly, there was Arizona, a far cry from Waylon's West Texas roots. In A place where from the jump. Too much of everything was never enough. And everything, remember, that's drugs, women and music. They went together in Phoenix. Waylon played every Tuesday through Saturday night at a place called JD's. And he started fooling around with a woman named Lynn Mitchell. Lynn Mitchell was not Waylon's wife. Not yet, anyway. His wife, at the time, Maxine, was back in Texas with the kids. Four of them now. And as you can imagine, given the fact that Maxine and Waylon were not living in the same state, the writing was on the wall. It was only a matter of time before Lynn Mitchell, here, Phoenix. Lynn Mitchell became the second Mrs. Jennings. And then only a matter of time after that before Lynn joined Maxine as another ex, collecting Waylon's alimony. You see the pattern here. But at the time, life was like a country song for Waylon Jennings. The kind he played at JD's, where he made his name. The kind he played out on the road, where he made his reputation. A reputation built on nights like this one. At a roadhouse club. More like a huge barn in the middle. Middle of nowhere. The show is over. Waylon is waiting to get paid. But there would be no payment tonight. Tonight there was just a shotgun, locked and loaded and the club owner's insistence that Waylon get the out. Fine. Waylon wasn't about to put up a fight. Not here. He and his band, the Wailers. Not like Bob Marley's band, but the Wailers, as in W A Y L O N. As in Waylon. Yeah, you get it. Anyway, the Wailers, along with Whelen's songwriting friend, Billy Joe Shaver, piled into Waylon's bus and hit the road. Waylon drove, the bus made its way up a dirt road toward the highway, the club behind them receding in the distance. Suddenly, there was a huge explosion. Billy Joe Shaver jumped in his seat and spun around out the bus's window. He could see the back half of the barn engulfed in flames, holding. Holy shit, Waylon. Did you see that? Waylon kept his hands on the wheel and his eyes on the road. I didn't see nothing. Word traveled. Just like the smoke traveled up to the heavens from that burning burn. One, he did not fuck with Waylon Jennings. And two, Waylon Jennings was the next big thing in country music. Nashville agreed to that second point. Specifically, Chet Atkinson, AKA the Country Gentleman, AKA one of the architects of the then modern Nashville sound. He signed Waylon to the RCA Victor label and then began to have him cut records that were more Chet Atkins vision than his own folk country love of the common people. The taker Tulsa Some of these are great albums that Waylon Jennings made inside the Nashville system, but none of them truly captured who he really was. That would come come later. And it didn't come without a fight. The fight started with a.22 Magnum pistol Whalen brought with him to the studio one afternoon. All these Nashville cats kept hitting those pickup notes on their instruments. Like the pedal steel player doing it now, that's to say playing notes during the intro of a song. The dovetail into the first full measure when the singer starts the verse. Totally unnecessary to Waylon's ears. You're cluttering up a good song with this. Whelan didn't want to hear any pickup notes on his records anymore. The pedal steel player, though, he kept playing them until Waylon cocked his gun. The next son of a bitch that hits one of them goddamn pickup notes is gonna get his goddamn fingers blown off. Cooler heads soon prevailed. The coolest belonging to Neil Reschin, who made his name doing Miles Davis taxes that was now managing Whelan. Neil Rushin was was a big deal because he single handedly discovered that RCA was screwing Whelan over. RCA said Whelan owed them money, but Neil Rushin proved it was actually the other way around. Furthermore, RCA had failed to comply with a renewal clause in Wayland's contract, which meant now Whelan had the upper hand when it came to the negotiations. 1972. Whelan and Neil Rushin sat in Chet Atkins office across the table from RCA executives. Waylon wanted freedom to do what he wanted. And that freedom, in Waylon's mind, should include an extra $25,000 in his coffers. It wasn't just about the respect that extra money provided. Waylon needed it. He had stacks of unpaid bills, alimony to not one, not two, but now three ex wives. RCA wasn't sympathetic and they weren't budging either. Their final offer was on the table to Waylon. To Neil, the offer was still $25,000 short. Both sides sat at the table in silence. Fuck this. Waylon had to take a piss. He didn't say anything about it. He just stood up and walked out. Minutes later, his bladder relieved, he emerged from the bathroom to find the meeting over and Neil Reschin waiting for him in the hallway. Waylon, he said. You're a fucking genius walking out of that meeting like that. That was the move we needed. What do you mean move? I decided to take a piss. Neil Rushin smiled But that, my friend, was a $25,000 piss. When Waylon stood up and left the negotiating table in silence, the suits at RCA freaked out. They asked Neil what Waylon was doing, and Neil, in all honesty, told him that he had no clue. You know Waylon. He's crazy. He'll do anything. Hell, maybe he's walking away right now and never coming back. RCA's hand was forced. Waylon got his money and his autonomy. All of which then gave the world honky tonk heroes, something like Waylon's 19th studio album, but arguably the first to present Waylon Jennings for real. The Nashville outlier. A heat packing, barn burning outlaw who took $25,000 pisses in the RCA bathroom. The guy who mashed together country and rock and roll like Elvis had done with country and blues all those years ago. Something new, something different, something daring. Just like Whelan himself. Now moving from one thing to the next. First buddy Hollywood, then pills, and now to the big game, where the stakes were higher than the uppers were, too. We'll be right back after this. Word. Word. Word.
- [26:22]
Carvana Representative
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- [26:55]
Kristen Bell
Hi, I'm Kristen Bell, and if you know my husband Dax, then you also know he loves shopping for a car. Selling a car, not so much.
- [27:01]
Jake Brennan
We're really doing this, huh?
- [27:03]
Kristen Bell
Thankfully, Carvana makes it easy. Answer a few questions, put in your VIN or license and done. We sold ours in minutes this morning and they'll come pick it up and pay us this afternoon.
- [27:14]
Jake Brennan
Goodbye, Truckee.
- [27:15]
Kristen Bell
Of course, we kept the favorite.
- [27:19]
Jake Brennan
Hello, other Truckee.
- [27:20]
Kristen Bell
Sell your car with Carvana today. Terms and conditions apply.
- [27:26]
Liquid IV Representative
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- [28:01]
Jake Brennan
Waylon Jennings dumped a quarter ounce of cocaine into the blender, followed by a gram of speed and one Quaalude. He hit the button that read puree or chop or liquefied. Didn't matter, they all did the same thing. He then poured the blended concoction into an empty aspirin bottle, which he tucked inside a cigarette pack, then stuffed into the top pocket of his vest, close enough to his face so that all he had to do when he wanted a bump was to stick a straw down into the pocket and the other end of said straw up his nose. But when it came to cocaine, Waylon Jennings didn't do bumps. As his son Terry wrote in his memoir, Waylon Jennings did thumps, waking himself up from a dead sleep at 2:3 in the morning to do more, buying it at $100 a gram, $1,500 a day. You do the math. He did enough blow in one afternoon for an entire football team. Oakland, California Raiders vs Chiefs halftime coach John Madden hit the locker room and pounded an entire bottle of Maalox. His team, the Oakland Raiders, were down six nothing. His players were beat up. One of his defensive tackles, a brick shithouse of a man, was puking his guts out. Madden began to draft a motivational pep talk in his head, but the Raiders needed something stronger than a pep talk. Thank God for Waylon Jennings, here now in the locker room at halftime, visiting his friend Kenny the Snake Stabler, the Raiders quarterback. Waylon had the remedy, as did Whelan's buddy Deacon Proudfoot, Hell's angel, current head of Whelen's security detail. That remedy, so to speak, was being doled out in the bathroom, thumps of cocaine that Waylon and Deacon were handing back and forth over the stalls. One line, two lines, Three, four. Shotgun style. That's half a gram of one nostril and one more of the other. Halftime was over, and the Oakland Raiders, high on Waylon Jennings cocaine, went back out onto the field at the Coliseum and proceeded to beat the ever loving shit out of the Kansas City Chiefs. Whelen, like the Oakland Raiders in the second half, was untouchable, not so much living outside the law as he was creating his own law. The music was undeniable. The Outlaws, a 1976 compilation album featuring songs by Whelan, Whelan's pals Willie Nelson and Tom McLaser, and Whelan's fourth and final wife, Jessie Colter was the first country record in history to sell a million copies. His next string of albums, Are you ready for the country? Waylon Live, Ol Waylon and Waylon and Willie all hit number one on the country chart. His success was hard fought. It was sweet. But when it came to Waylon's finances, success wasn't enough to break even. Alimony, back taxes, all manner of delinquents putting a strain on the payroll. The kind of situation that leads to taking bigger chances. Chances and bigger risks. August 24, 1977American sound recording Studio Nashville. Little over a week since the King himself, Elvis Presley, took his last seat on a porcelain throne. Waylon was eager to finish laying down this harmony track on his wife Jesse's new song. Equally eager to then dip into the stash of cocaine sitting at his feet. One kilo he'd just had sent to him through the mail. Drugs via the United States postal system. Just the sort of brass balls outlaw move that only Waylon Jennings could pull off. Or so the thinking went. On the other side of the double glass wall in the control room where Waylon's drummer, Richie Albright was running the recording session, the outside door flew open. Two men stepped inside. DEA agents who had been tracking Whelan's package of cocaine. Richie was fast. He thought fast, acted fast. He leaned back against the recording console and pressed his hand down on the talkback button. Now this is an important detail. The American Sound recording studio was equipped with a Harrison mixing console, which unlike most mixing consoles at the time, had a talkback button that when pressed, allowed both the control room where Richie was and the studio room where Waylon was, and to simultaneously talk to and hear each other. Other consoles only allowed for one way communication. So Richie Albright, without the DEA agents knowing, was allowing Waylon through the headphones he was wearing in the studio to hear this entire conversation with the feds as it unfolded. So Richie says, can I help you boys? This is a closed session. Agent Number One goes, what happened to that package that was just delivered? Richie goes, do y' all have a warrant? Agent 1 says, we have a warrant for Waylon Jennings arrest. Richie. Listen boys, I'd love to help you, but we're right in the middle of one last vocal take. This place is like 200 bucks an hour. Can we just finish the take and then Waylon is all yours. Agent number Two looked at agent Number One and gave a curt nod of approval. Richie ran the tape from the top and Waylon began to sing again. Halfway through the Chorus. Richie stopped the tape. Kate and pressed on the Harrison talk back button again. Waylon. I'm sorry, Hoss, but there's something wrong with your microphone. Let me come in there real quick and swap it out for another. The agents waited impatiently. Richie slipped into the studio room, replaced the mic, and then, very carefully, without anyone noticing, removed the bags of cocaine from the box at Waylon's feet and slid them down the front of his jeans. Minutes later, he was flushing the contents down the toilet in the studio bathroom while the DEA agents grilled Waylon. Where I come from, Waylon said, possession means got it. And you boys ain't got it. The DEA didn't have to have anything. They knew Waylon was dirty. They arrested him anyway, charging him with possession and conspiracy. The case dragged on for months. Months. Months in which Waylon's paranoia ran as high as his continuing drug intake. He checked every phone for bugs. He hired former FBI agents to sweep his house. But the case against him only made his reputation stronger. He was a modern day Robin Hood or Billy the Kid. He used that rep to his advantage with his next single, don't you think the outlaw bits done got out of hand. The song essentially confessed to the crime he was currently fighting and it peaked at number five on the country chart. That song, the attention, none of it got Waylon Jennings what he really needed. Neither did his new role on the Dukes of Hazzard as the balladeer singer of the popular TV show's theme song. Waylon needed money. The kind of money that could support all those ex wives, the taxman, a bloated payroll. And that wasn't all. When the government finally dropped the cocaine charges, charges, Waylon owed something like a hundred thousand dollars in legal fees. His bank account balance was at negative 860 grand. I'm not even sure how that's possible. The bank froze everything. By the early 1980s, the only thing higher than Waylon Jennings was his impossibly tall mountain of debt. No matter how dire his financial situation, Waylon Jennings surrounded himself with people who believed in him, just like Buddy Holly had believed in him all those years before. These days, it was the Hells Angels Motorcycle Club. The bikers saw in Waylon Jennings a kindred spirit. They were drawn to him like so many others who, let's be honest, were a part of the larger problem, at least when it came to Waylon's bottom line. But the Angels were tough guys, reinforcing Waylon's air of toughness. Like Deacon Proudfoot and Boomer Baker. Boomer Had a mouthful of gold teeth. And he walked with a cane that had a gold skull on top. He was there to protect and serve. Like on the night he stood watch outside Waylon's hotel room, armed to the teeth. Guns, knives, a grenade even. On account of the rumor going around that a rival motorcycle club, in their quest to become bigger and more powerful than the Angels, had put a hit out on Whelan or a member of his family. A family that Boomer took care of. Not least of which was Whelan's youngest son, Shooter, now a great musician and producer in his own right. But back in the day, a little toddler being raised by outlaws. Outlaws like Boomer Baker. Outlaws like his father. A father who was now watching as his son, shooter, just 3 years old, found one of Waylon's coke straws and stuck it up his nose, doing like his daddy did. That shook Waylon. Being a badass was one thing. Being a bad role model was something else entirely. Waylon decided to rent a house in Arizona. Not in Phoenix, where he'd first meet his bones as a performer, but way out in the desert, where he was at the mercy of the elements. Zero distractions. No band members, no bikers. Just Waylon and his wife, Jesse. He had to clean up everything. His finances and also his habit. March, 1984. Whelen climbed into his tour bus and did as much cocaine as he could handle. One last hurrah. Then he exited the bus and walked in, into his rented house, leaving about 20 grand worth of cocaine behind. Call it cold turkey, with a safety net, a little insurance in case what he was about to do proved too difficult. And it was difficult. As soon as that final high wore off, his bones began to ache. His entire body shook violently. He was sick. He couldn't sleep. He knew he could end this awful feeling just by going back to the bus, where piles of cocaine were waiting. But he didn't. He'd made up his mind. Waylon Jennings didn't do what he didn't want to do. Not picking cotton, not going to school, not conforming to the Nashville machine. And not cocaine. Not anymore. A month later, Whelen stepped foot out of that rented home. A new man. He told Jesse to get rid of the drugs. She dumped all. All $20,000 worth down the drain, yelling hallelujah as she did it, ecstatic that her husband, Waylon Jennings, was a survivor, a trailblazer, A total badass. And he was no longer a disgrace. I'm Jake Brennan, and this is disgrace. All right. Thank you. For hanging out with me and the one and only Waylon Jennings Apple Podcast listeners. If you have not already, please turn on auto downloads so you don't miss any of our episodes. Listen Waylon Jennings complete and total lunatic. Known as one of the outlaw country singers. But my question of the week for you guys is was Waylon Jennings the most punk rock of the country sing singers? If not, who was Hit me up. Lot of candidates. 617-90-66638 I want your answers. You can leave a voicemail or a text. You can also DM me disgracelandpod email me disgracelandpod gmail.com we'll place some of your answers on the upcoming afterparty episodes. All right guys, I gotta take off. Got some credits coming up right now. Disgraceland was created by yours truly and is produced in partnership with Double and Elvis. Credits for this episode can be found on the show notes page@gracelandpod.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 us on Instagram, TikTok, Twitter and Facebook Disgracelandpod and on YouTube@YouTube.com Disgracelandpod Rocka Rolla He's a bad, bad man.
- [40:42]
Carvana Representative
Thanks for selling your car to Carvana. Here's your check.
- [40:44]
Jake Brennan
Whoa. When did I get here?
- [40:46]
Carvana Representative
What do you mean?
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Jake Brennan
I swear it was just moments ago that I accepted a great offer from Carvana online. I must have time traveled to the future.
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Carvana Representative
It was just moments ago. We do same day pickup. Here's your check for that great offer.
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Jake Brennan
It is the future. It's.
- [40:59]
Carvana Representative
It's the present. And just the convenience of Carvana. Sorry to blow your mind.
- [41:03]
Jake Brennan
It's all good. Happens all the time.
- [41:05]
Carvana Representative
Sell your car the convenient way to Carvana. Pickup times may vary and fees may apply.