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Waylon Jennings gave up his spot on a flight that changed music history. His mentor, Buddy Holly, took that seat and was killed when the plane crashed. Born dirt poor, Jennings went from country disc jockey to country superstar, leading the revolution in country music with his platinum album The Outlaws. Through his eyes we see the Nashville scene in the early days, and through his honest, no-holds-barred storytelling, we follow his struggle to overcome drugs and impending bankruptcy to establish himself as one of the living legends of country music.