Waylon Jennings was hired by Holly to play bass for him on the Winter Dance Party Tour, which began January 23rd, 1959, in Milwaukee. Jennings, 21 at the time, had been in New York City recording sessions produced by Holly, and after taking a train to Chicago, met up with the rest of Holly’s band. Problems first arose when the tour buses hired to transport the group began breaking down. After a show in Clear Lake, Iowa, on February 2nd, Holly decided to charter a plane for himself, guitarist Tommy Allsup and Jennings so they could fly to Fargo, North Dakota, instead of taking the long, frozen bus trip. Richardson, who was suffering from the flu, asked Jennings for his seat on the plane, and Valens asked the same of Allsup. When Jennings told Holly that he was going to take the bus, Holly jokingly told him he hoped the bus broke down, to which Jennings replied, “I hope your ol’ plane crashes.” “God almighty, for years I thought I caused it,” the country legend said decades later in a CMT interview.] Waylon Jennings was hired by Holly to play bass for him on the Winter Dance Party Tour, which began January 23rd, 1959, in Milwaukee. Jennings, 21 at the time, had been in New York City recording sessions produced by Holly, and after taking a train to Chicago, met up with the rest of Holly’s band. Problems first arose when the tour buses hired to transport the group began breaking down. After a show in Clear Lake, Iowa, on February 2nd, Holly decided to charter a plane for himself, guitarist Tommy Allsup and Jennings so they could fly to Fargo, North Dakota, instead of taking the long, frozen bus trip. Richardson, who was suffering from the flu, asked Jennings for his seat on the plane, and Valens asked the same of Allsup. When Jennings told Holly that he was going to take the bus, Holly jokingly told him he hoped the bus broke down, to which Jennings replied, “I hope your ol’ plane crashes.” “God almighty, for years I thought I caused it,” the country legend said decades later in a CMT interview.
