

Waylon Jennings: Surviving Buddy Holly, the DEA, and Himself
Jul 22, 2025
Explore Waylon Jennings' heartbreaking choice to give up a seat on a fateful plane, which claimed buddy Buddy Holly's life. Delve into his journey of grief and guilt, leading to a fervent quest for artistic freedom. Experience wild tales of his chaotic lifestyle, including run-ins with the DEA and notorious drug use at a Raiders game. Witness his poignant struggle towards sobriety, supported by his wife, marking a turning point in his life. This is a gripping tale of music, addiction, and resilience.
AI Snips
Chapters
Books
Transcript
Episode notes
Plane Seat Switch and Tragic Crash
- Waylon Jennings gave up his plane seat to Big Bopper, sparing his life but losing Buddy Holly and others in a crash.
- He was haunted by guilt and forced to impersonate Buddy Holly in subsequent shows after the crash.
Hiding Pills from Johnny Cash
- Waylon Jennings hid his pills inside the wall switch panel of his apartment to keep them from Johnny Cash.
- This method meant destroying the wall to retrieve his stash, showing the lengths he went to hide his addiction.
The $25,000 Piss Negotiation
- Waylon walked out of a contract negotiation and took a bathroom break, which forced RCA to meet his $25,000 demand.
- This "$25,000 piss" gave him creative freedom and financial gain.