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

DISGRACELAND

Jake Brennan

True Crime, Music, Society & Culture

4.6 • 13.1K Ratings

🗓️ 22 July 2025

⏱️ 38 minutes

🔗️ Recording | iTunes | RSS

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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. To see the full list of contributors, see the show notes at www.disgracelandpod.com. This episode was originally published on June 27, 2024. Sign up for our newsletter and get the inside dirt on events, merch and other awesomeness - GET THE NEWSLETTER Follow Jake and DISGRACELAND: Instagram YouTube X (formerly Twitter) Facebook Fan Group TikTok 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

Transcript

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1:07.9	Disgraceland is a production of Double Elvis.
1:24.4	Music Disgraceland is a production of Double Elvis. The stories about Wayland Jennings are insane.
1:29.3	He gave up his seat on a plane hours before it crashed and killed, among others, Buddy Holly.
1:35.3	He stashed his pills in the wall of his apartment to hide them from his pillhead roommate, Johnny Cash.
1:41.4	He did blow during halftime of an NFL game with the Oakland Raiders,
1:46.8	pulled a loaded gun in the recording studio,
1:49.5	and was arrested by the DEA after a kilo of cocaine was sent to him in the mail.
1:55.6	Waylon Jennings was a badass and a taker of no shit,
	...

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