Problems first arose when the tour buses hired to transport the group began breaking down. 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. 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. ![]() Less than six miles northwest of the airport where it took off, the plane went down, killing all onboard. 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. ![]() 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.
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