The day the music died. That's how songwriter Don McLean memorialized February 3rd, 1959, in his 1972 single "American Pie," an epic, eight-minute music-history lesson that begins with a reference to the plane crash that killed musicians Buddy Holly, J.P. Richardson (a.k.a. the Big Bopper) and Ritchie Valens, along with the pilot of the 1947 Beechcraft Bonanza that had been chartered to transport the performers from Iowa to their next show in Minnesota. Less than six miles northwest of the airport where it took off, the plane went down, killing all onboard.
One member of Holly's band who did not make the trip went on to become a country music trailblazer, one of the genre's original "outlaws." 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.
"The only reason Buddy went on that tour was because he was broke. Flat broke," Jennings revealed to Rolling Stone in 1973. "He didn't want to go, but he had to make some money. I ain't sayin' the person's name that was the reason he was broke."
Although "Jole Blon," one of the tracks produced by Holly, was only a minor success for Jennings, he would go on to become one of the most influential country acts of the Seventies. In 1976, Wanted: The Outlaws, which also featured his wife Jessi Colter, Willie Nelson and Tompall Glaser, was the first country album ever to be certified as a million-seller. In 2001, Jennings was inducted into the Country Music Hall of Fame, although the ailing icon sent his son Shooter to accept the honor in his place. Following complications from diabetes, Jennings died in Arizona in February 2002.