Waylon Jennings: Surviving Buddy Holly, the DEA, and Himself

Summary

DISGRACELAND – Waylon Jennings: Surviving Buddy Holly, the DEA, and Himself

Podcast: DISGRACELAND
Host: Jake Brennan (Double Elvis Productions)
Episode Release: March 20, 2026
Episode Theme:
A high-octane, true-crime-laced deep dive into the chaotic, mythic, and often dangerous life of country legend Waylon Jennings—his brushes with tragedy, addiction, the law, and his own outsize will to survive (and thrive) on his own terms.

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Main Theme & Purpose

This episode peels back the curtain on Waylon Jennings, painting an electrifying portrait of the outlaw country icon—his transformation from West Texas radio DJ to Buddy Holly's bassist, his survival of "the day the music died," his tumultuous relationships with drugs, women, and the Nashville establishment, and his near-mythical status as both a badass and a survivor. Through drama, dark humor, and reverence for music history, DISGRACELAND showcases how Jennings didn’t just make great music—he lived an often dangerous, legendary life that defied genre and rules.

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Key Discussion Points & Insights

1. Early Life & Rebellion Against Convention

• West Texas Roots & Early DJ Years
  • Waylon starts as a radio DJ in Lubbock, Texas, spinning the music he likes—country, blues, and especially R&B, despite station objections.
  • He’s fired for going off-script (“playing Little Richard and Ray Charles back to back”) but remains undeterred, doubling down on what feels right to him.
  • Quote (Jake Brennan, 05:40):

    "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."

2. Friendship with Buddy Holly & The Plane Crash That Changed Everything

• Buddy Holly’s Faith in Waylon
  • Buddy’s confidence lifts Waylon out of the DJ booth; Buddy teaches him bass and brings him on tour.
  • Heartfelt scene in a New York photo booth, capturing the two friends’ camaraderie.
  • Quote (Jake Brennan, 10:47):

    "Buddy Holly was a drug. That drug empowered Whelan and the others through a grueling tour, night after night, city after city."

• The Day the Music Died
  • Waylon gives his seat to a sick Big Bopper; Tommy Allsup loses his to Ritchie Valens in a coin toss.
  • Final words between Waylon and Buddy are laced with dark humor that would haunt Waylon for decades.
  • Quote – Buddy Holly to Waylon (Jake Brennan reads, 11:23):

    "I hope your damn bus freezes up."
    Waylon: "I hope your old plane crashes."

• Aftermath & Survivor’s Guilt
  • Waylon is forced to impersonate Buddy onstage out of contractual obligation—“made to perform as his dead friend.”
  • He returns to Texas, traumatized, with nothing but Holly’s bass and a future riddled with guilt and pills.
  • Quote (Jake Brennan, 12:41):

    "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..."

3. The Pill-Soaked Underbelly of 1960s Nashville

• Drugs as Part of the Music Industry Fabric
  • Pills (“white crosses, speckled birds, L.A. turnarounds”) are cultural currency; addiction is normalized and often overlooked.
  • Memorable scenario (Jake Brennan, 18:39):

    "Waylon Jennings had been awake for days, clutching a fistful of pills, while three different women waited for him in three different rooms... Waylon, Richie said, you're going to kill yourself. Waylon couldn't argue with that. He never knew when enough was enough."

• Rooming with Johnny Cash
  • Both hide their pill stashes from each other (“Stashing pills was a fluid game”); paranoia and addiction forge unreliable alliances.

4. Arizona Years, Women, and the Making of an Outlaw

• Phoenix, Infidelity, and Barroom Escapades
  • Pattern of failed marriages emerges—"the writing was on the wall."
  • Escapes a roadhouse conflict as the club goes up in flames; unspoken implication of outlaw retribution—“He and his band... piled into Whelan's bus... Suddenly, there was a huge explosion.”
• Birth of ‘Outlaw’ Reputation
  • Gritty, no-nonsense approach to gigs and life—resistance to conforming (even under the “Nashville system”).
  • Showdown with session musicians ends with Waylon threatening to shoot off fingers if they add unwanted “pickup notes.”

5. Breaking Free from Nashville’s Control

• Negotiating Autonomy
  • With savvy manager Neil Reschin, Waylon secures creative freedom and back pay in a pivotal move—a literal $25,000 bathroom break.
  • Quote (Jake Brennan, 27:13):

    "When Waylon stood up and left the negotiating table in silence, the suits at RCA freaked out... Neil Reschin smiled. Well, that, my friend, was a $25,000 piss."

• Honky Tonk Heroes and Outlaw Country
  • Waylon’s true voice emerges; finally “from For Real, the Nashville outlier... the guy who mashed together country and rock and roll like Elvis had done with country and blues.”

6. Escalation: Cocaine, the DEA, and Living on the Edge

• Epic Substance Abuse
  • Waylon's drug rituals grow extravagant—mixing cocaine, speed, and Quaaludes in a blender, consuming it through a straw in his vest pocket (“Waylon Jennings did thumps”).
  • Wild stories: Coked-out at Oakland Raiders halftime, enabling the team’s second-half comeback.
• DEA Raid & Narrow Escape (32:26 – 37:47)
  • Waylon receives a kilo of cocaine by mail, DEA agents burst in mid-session; Richie Albright, his drummer, outsmarts the Feds by using the studio “talkback button” to warn Waylon and dispose of the evidence.
  • Quotable (Jake Brennan, 36:53):

    "Where I come from, Waylon said, possession means got it. And you boys ain't got it."

  • He’s arrested anyway—an outlaw now in the eyes of law and legend.

7. Fame, Fortunes Lost, and Role Model Reckoning

• Chart Success and Financial Ruin
  • Despite multiple #1 albums and million-selling records, Waylon is strapped for cash, bled by alimony, taxes, and a bloated entourage.
• Hell’s Angels and Outlaw Kinship
  • Attracts biker muscle—bodyguards with grenades and gold teeth.
  • Realization strikes hard when his young son mimics his cocaine use.
  • Turning Point (Jake Brennan, 41:25):

    "That shook Waylon. Being a badass was one thing. Being a bad role model was something else entirely."

8. Kicking Drugs & Redemption

• Cold Turkey in the Arizona Desert
  • Waylon locks himself away with his fourth wife Jessie, toughs through withdrawal, and orders her to “get rid of the drugs” once he’s clean.
  • Quote (Jake Brennan, 42:28):

    "She dumped all $20,000 worth down the drain, yelling hallelujah as she did it... Waylon Jennings, was a survivor, a trailblazer, a total badass. And he was no longer a disgrace."

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Memorable Moments & Notable Quotes

• “He did blow during halftime of an NFL game with the Oakland Raiders... pulled a loaded gun in the recording studio... 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.” (Jake Brennan, 03:10)
• “Pills were the gasoline in the Music City tank, a cultural currency second only to the music.” (Jake Brennan, 19:35)
• “The next son of a bitch that hits one of them goddamn pickup notes is gonna get his goddamn fingers blown off.” (Jake Brennan as Waylon, 23:21)
• “When Waylon stood up and left the negotiating table in silence, the suits at RCA freaked out... Well, that, my friend, was a $25,000 piss.” (Jake Brennan quoting Neil Reschin, 27:13)
• “Waylon Jennings did thumps... $1,500 a day... You do the math.” (Jake Brennan, 32:37)
• “Where I come from... possession means got it. And you boys ain't got it.” (Jake Brennan as Waylon, 36:53)
• “Being a badass was one thing. Being a bad role model was something else entirely.” (Jake Brennan, 41:25)
• “Waylon Jennings, was a survivor, a trailblazer, a total badass. And he was no longer a disgrace.” (Jake Brennan, 42:41)

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Timestamps for Important Segments

• Waylon's Early Years & Buddy Holly – 03:05 to 14:27
• Pill Culture & Nashville Struggles – 18:39 to 21:08
• Flight from Nashville Conventions – 23:21 to 27:41
• Honky Tonk Heroes & Outlaw Country – 27:41
• Drug Stories & the Oakland Raiders – 32:26 to 34:53
• DEA Bust & Studio Drama – 34:53 to 37:47
• Financial Struggles, Outlaw Reputation Reinforced – 38:24
• Hell’s Angels, Family, and Kicking Cocaine – 39:41 to 42:41

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Final Reflection & Listener Engagement

Jake Brennan invites listeners to consider: “Was Waylon Jennings the most punk rock of the country singers? If not, who was?” (43:40) And highlights the legacy of Waylon as both total lunatic and revered legend.

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Conclusion

Waylon Jennings’ story—rife with survivor’s guilt, substance abuse, standoffs with law and label, and hard-won redemption—proves him not only unbreakable, but uniquely American: stubborn, wild, inventive, and ultimately, uncontainable.

For fans of music, true crime, and myth-busting, this episode delivers high drama, gritty details, and a deeper understanding of Waylon Jennings—the man who outlived the crash, the drugs, the establishment, and finally, himself.

Transcript

[Ryan Seacrest]

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[Public Podcast Sponsor / Host]

Support for the show comes from Public, the investing platform for those who take it seriously. On Public you can build a multi asset portfolio of stocks, bonds, options, crypto and now generated assets which allow you to turn any idea into an investable index with AI. It all starts with your prompt. From renewable energy companies with high free cash flow to semiconductor suppliers growing revenue over 20% year over year, you can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one of a kind index and lets you back tested against the S&P 500. Then you can invest in a few clicks. Generated assets are like ETFs with infinite possibilities, completely customizable and based on your thesis, not someone else's. Go to public.com podcast and earn an uncapped 1% bonus when you transfer your portfolio. That's public.com podcast paid for by Public Investing Brokerage Services by Open to the Public Investing Inc. Member FINRA and SIPC Advisory Services by Public Advisors llc. SEC Registered Advisor Generated Assets is an interactive analysis tool. Output is for informational purposes only and is not an investment recommendation or advice. Complete Disclosures available at public.comdisclosures

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[Jake Brennan]

Disgraceland is a production of Double Elvis. The story is about Waylon Jennings. Runnings are insane. He gave up a 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. Arrested 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 disgrace. 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 in 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 B, he loved it all and he played it all, especially Little Richard. Tutti Frutti 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 Whelen 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 Whelen'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 Waylon 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 instrumental choice guitar, but Buddy believed in him. Waylon 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 Waylon 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. Whalen 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 Whelan 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 Asa. But just hours before the flight, the Big Bopper, hit hard with the flu, asked Waylon if he would consider giving up his seat. Whalen could see that the Bopper in 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 shit. You're not going with me tonight, huh? What, did you chicken out? It's not like that. Waylon told him the Big Bopper's sick, and it seemed like the right thing to do. Okay, then, Buddy said, again with the shit talking, I hope your damn bus freezes up. Well, Waylon responded, I hope your old plane crashes.

[Public Podcast Sponsor / Host]

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 Ballin, 17, Buddy Holly, 22 and JP Richardson, known professionally as the Bait Bopper. Their small, charted 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.

[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 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 Allsup 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 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 Lion 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 Opry crackling out of the car's radio.

[Ryan Seacrest]

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[Public Podcast Sponsor / Host]

Support for the show comes from Public, the investing platform for those who take it seriously. On Public you can build a multi asset portfolio of stocks, bonds, options, crypto and now generated assets which allow you to turn any idea into an investable index with AI. It all starts with your prompt. From renewable energy companies with high free cash flow to semiconductor suppliers growing revenue over 20% year over year, you can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one of a kind index and lets you back test it against the S&P 500. Then you can invest in a few clicks. Generated assets are like ETFs with infinite possibilities, completely customizable and based on your thesis, not someone else's. Go to public.com podcast and earn an uncapped 1% bonus when you transfer your portfolio. That's public.com podcast paid for by Public Investing Brokerage Services by Open to the Public Investing Inc. Member FINRA and SIPC Advisory Services by Public Advisors llc. SEC Registered Advisor Generated Assets is an interactive analysis tool. Output is for informational purposes only and is not an investment recommendation or advice. Complete Disclosures available at public.comdisclosures

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[Jake Brennan]

Waylon Jennings had been awake for days, clutching a fistful of pills, while three different women waited for him in three different rooms. 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 of you aforementioned pills were waiting. White crosses, speckled birds, L.A. 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 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 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 of nowhere. The show was over. Waylon was 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 fuck 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 wa y l O N. As in way low. Yeah, you get it. Anyway, the Wailers, along with Waylon's songwriting friend, Billy Joe Shaver, piled into Whelan'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. Holy shit, Whaley. 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 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 later. And it didn't come without a fight. The fight started with a.22 Magnum pistol Waylon 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 that 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 bullshit. Waylon 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 Rushin, who made his name during Miles Davis's 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. Whelan 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. Well, 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 from 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.

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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 and 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 mahlox. 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 Waylon's buddy, Deacon Proudfoot, Hell's angel, current head of Waylon'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. Wayland. 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. Whalen, 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 Waylon, Waylon's pals Willie Nelson and Tomville Glaser, and Whelan's fourth and final wife, Jesse Coulter, was the first country record in history to sell a million copies. His next string of albums, Are youe Ready for the Country, Waylon Love, 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 Whelan'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 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 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 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 number One 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 table tape and pressed on the Harrison talkback 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 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 charge charges, Waylon owed something like a hundred thousand dollars in legal fees. His bank account balance was 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 Hell's 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 was walked 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, Waylon stepped foot out of that rented home. A new man. He told Jesse to get rid of the drugs. She dumped 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.

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All right.

[Jake Brennan]

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 singers? If not, who was Hit me up. Lot of candidates 617-906-6638 I want your answers. You can leave a voicemail or a text. You can also DM me at Disgracelandpod. Email me disgracelandpodmail.com we'll place some of your answers on the upcoming After Party episodes. Alright guys, I gotta take off. Got some credits coming up right now. Disgraceland was created by yours truly and is produced in part partnership with Double Elvis. Credits for this episode can be found on the show notes [e-mail] 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 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 [e-mail] Disgracelandpod Rocka Rolla

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