Waylon Jennings: Surviving Buddy Holly, the DEA, and a $25,000 Piss

DISGRACELAND

Jake Brennan

True Crime, Music, Society & Culture

4.6 • 13.1K Ratings

🗓️ 22 July 2025

⏱️ 37 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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0:00.0	Double Elvis.
0:06.0	Oh, that's my prime delivery.
0:09.0	What, already?
0:10.0	Only one thing can match the buzz of Primes fast delivery.
0:13.0	And that's the buzz of Primes entertainment.
0:16.0	What are we watching?
0:17.0	Heads of State, that new action comedy with Idris Elba as the Prime Minister,
0:20.0	John Sina as the president and Priyanka Chopra Jonas as their only hope. Looks like a blast. From fast delivery to explosive entertainment, it's on Prime. For only $899 a month, join now. Content includes limited ads, subscription or to run news. For more information, go to amazon.com. U.K.S. Prime. So, what are you watching at the moment?
0:38.9	Squid game, Dad.
0:40.2	Let's watch it together this weekend. That'd be nice. What's it on again? Netflix. You've got EETV, so you just switch it on. What season are we up to? Um, four? That's Stranger Things, Mom. And what about the kids?
0:34.6	Don't worry, they'll watch Coca-Mellon for the hundredth time.
0:37.8	Switch on Netflix with EETV, plus change ups things, Mom. And what about the kids? Don't worry, they'll watch Colcomellon for the hundredth time.
0:55.1	Switch on Netflix with EETV,
0:57.4	plus change up sports and entertainment.
0:59.6	It's TV with the ultimate flex for the whole family.
1:02.6	EETV requires EE broadband,
1:04.4	separate 24-month contracts for TV and broadband content may vary time supply.
1:08.0	Disgrace and is a production of Double Elvis.
1:10.2	Music Disgrace Land is a production of Double Elvis.
1:28.5	The stories about Wayland Jennings are insane.
1:34.8	He gave up his seat on a plane hours before it crashed and killed, among others, Buddy Holly.
1:41.0	He stashed his pills in the wall of his apartment to hide them from his pillhead roommate, Johnny Cash.
	...

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