Waylon Arnold Jennings (June 15, 1937 – February 13, 2002) was an American singer, songwriter, musician, and actor. Jennings began playing guitar at eight and began performing at 14 on KVOW radio. His first band was The Texas Longhorns. In 1958, Buddy Holly arranged Jennings's first recording session and hired him to play bass. In Clear Lake, Iowa, Jennings gave up his seat on the ill-fated flight that crashed and killed Holly, J. P. Richardson, Ritchie Valens, and pilot Roger Peterson.

The Winter Dance Party tour began in Milwaukee, Wisconsin, on January 23, 1959. The amount of travel created logistical problems, as the distance between venues had not been considered when scheduling each performance. Adding to the problem, the unheated tour buses twice broke down in freezing weather, with dire consequences. Holly's drummer Carl Bunch suffered frostbite to his toes and was hospitalized. Buddy Holly made the decision to find another means of transportation. Before their performance at the Surf Ballroom in Clear Lake, Iowa, Holly chartered a four-seat Beechcraft Bonanza airplane at Dwyer Flying Service in Mason City, Iowa, for himself, Jennings, and Tommy Allsup, to avoid the long bus trip to their next venue in Moorhead, Minnesota. Following the Clear Lake show Allsup lost a coin toss and gave up his seat on the charter plane to Ritchie Valens, while Waylon Jennings voluntarily gave up his seat to J. P. Richardson, who was suffering from the flu.

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