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Waylon Jennings, Cocaine, and a DEA Raid Gone Wrong

May 6, 2026 · 1 h 4 min

Show notes

Waylon Jennings didn't just sing songs about being an outlaw. He genuinely became one.

In this week's Tape Spaghetti, Scott & Blake discuss the life and legend of Waylon Jennings, who went from small-town disc-jockey to Buddy Holly's bandmate to one of country's greatest rebels.

Back when Nashville was a highly polished music machine, Jennings forged his own gritty sound... and even grittier lifestyle. It all culminated in a raid of his recording studio by DEA agents in search a suspicious package, which vanished in just about the most absurd way possible.

Here's the story of Waylon Jennings as a myth-making outlaw country star, the tension between artists and Nashville overlords, and a dash of true crime that seems too crazy to be true.

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