Episode #183 | 7.21.25

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

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In this episode

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.