Waylon Jennings: Surviving Buddy Holly, the DEA, and Himself
DISGRACELAND
Exactly Right and iHeartPodcasts
4.6 • 13.4K Ratings
🗓️ 20 March 2026
⏱️ 34 minutes
🧾️ Download transcript
Summary
Waylon Jennings’ musical career began with tragedy. On tour as the bass player for his friend Buddy Holly, Waylon gave up his seat on the tiny plane that, just hours later, crashed, killing Buddy and three others. That experience alone nearly put an end to Waylon’s musical dreams. But he continued, persevering by doing only the things he wanted to do – which included hiding his pill stash from his roommate Johnny Cash, hiding his coke stash from the DEA, and creating a county/rock hybrid that refused to conform or even obey the law.
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This episode was originally published on June 27, 2024.
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Transcript
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| 0:00.0 | Disgraceland is a production of Double Elvis. |
| 0:17.0 | The stories about Wayland Jennings are insane. |
| 0:21.9 | He gave up his seat on a plane hours before it crashed and killed, among others, Buddy Holly. |
| 0:28.2 | He stashed his pills in the wall of his apartment to hide them from his pillhead roommate, Johnny Cash. |
| 0:34.4 | He did blow during halftime of an NFL game with the Oakland Raiders, pulled a loaded |
| 0:40.2 | gun in the recording studio, and was arrested by the DEA after a kilo of cocaine was sent to him |
| 0:46.8 | in the mail. Whalen Jennings was a badass and a taker of no shit, a major player in the formative days of both rock and roll |
| 0:56.9 | and outlaw country. And he made, of course, great music. Unlike that loop I played for you at the |
| 1:04.3 | top of the show, that wasn't great music. That was a preset loop from my Melotron called |
| 1:10.5 | John Hughes Fever Dream, MK, 2. |
| 1:14.7 | I played you that loop because I can't afford the rights to best of my love by the emotions. |
| 1:21.5 | And why would I play you that specific slice of whoa, whoa, whoa, oh, cheese, could I afford it? |
| 1:28.6 | Because that was the number one song in America on August 24, 1977. |
| 1:35.5 | And that was the day that federal agents raided a Nashville studio in the middle of a |
| 1:40.3 | recording session with a warrant for Wayland Jennings' arrest. |
| 1:44.6 | On this episode, a plane crash, pill stashes, |
| 1:49.1 | coked up Oakland Raiders, loaded guns, badasses, and Wayland Jennings. |
| 1:55.5 | I'm Jake Brennan, and this is Disgraceland. |
| 2:32.0 | Thank you. and this is Disgraced Land. You know when you have a great idea? |
| 2:35.1 | Maybe you've finally figured out what the meaning of life is, |
| 2:38.5 | 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, |
| 2:42.1 | whatever, it doesn't matter. |
... |
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