The Six Words That Haunt Waylon Jennings After Buddy Holly's Death: "Well, I hope your ol' plane crashes." On February 3, 1959, before the tragic plane crash known as "The Day the Music Died," Waylon Jennings was touring with Buddy Holly, Ritchie Valens, and The Big Bopper (J.P. Richardson). Due to the harsh winter conditions and issues with their tour bus, Holly decided to charter a small plane to fly to their next destination, Fargo, North Dakota. Jennings, a member of Holly's band at the time, was initially supposed to be on the flight. However, Jennings gave up his seat to The Big Bopper, who was suffering from the flu and needed a more comfortable travel arrangement. When Holly learned that Jennings wasn't going to fly, he jokingly said, "Well, I hope your ol' bus freezes up." Jennings replied in jest, "Well, I hope your ol' plane crashes." Tragically, the plane did crash later that night, claiming the lives of Holly, Valens, and The Big Bopper. Jennings was devastated by the loss of his friends and deeply regretted his parting words to Holly. The incident haunted him for the rest of his life, and he often spoke about the guilt he felt in interviews.