On February 3, 1959—now known as “The Day the Music Died”—country legend Waylon Jennings narrowly escaped a tragic fate. He was supposed to be on the doomed plane that crashed near Mason City, Iowa, killing rock pioneer Buddy Holly, Ritchie Valens, and The Big Bopper (J.P. Richardson).
Jennings, who played bass for Holly at the time, gave up his seat to The Big Bopper, who was battling the flu and needed a quicker way home. Before takeoff, Holly jokingly told Jennings, “I hope your ol’ bus freezes up.” In a haunting response that allegedly haunted Jennings until his death in 2002, Jennings replied, “Well, I hope your ol’ plane crashes.”
Just five minutes after takeoff, the plane crashed into an Iowa cornfield, killing everyone on board. Investigators determined that poor weather and an untrained pilot were to blame. Holly was just 22, Valens 17, and The Big Bopper 28.
Heartbreakingly, Holly’s wife, Maria, found out about his death on television, which led to a miscarriage due to sho...