Waylon was being managed by Buddy Holly 's former first manager ' Hi-Pockets ' Duncan who recommended Waylon to Buddy . With money out of his own pocket , Buddy produced Waylon 's first record , a Rock & Roll version of ' Jolie Blon ' & Waylon is considered to be Buddy 's ' protoge ' . In 1959 Buddy Holly hired Waylon Jennings to play electric bass for him during his " Winter Dance Party Tour " . After a show in Clear Lake , Iowa , Holly chartered a plane for himself , Allsup and Jennings to avoid a long bus trip to Fargo , North Dakota . This is because the tour organizers provided very inadequate transportation & the buses broke down in freezing weather . Jennings gave up his seat to J. P. Richardson , who was suffering from a cold and complaining about how uncomfortable a long bus trip was for a man of his size . During the early morning hours of February 3 , 1959 , later known as The Day the Music Died , the charter crashed outside Clear Lake , killing all on board . Jennings and Allsup continued the tour for two more weeks , featuring Jennings as the lead singer . When the tour ended , he returned to his DJ spot on KLLL and performed regionally
The Day the Music Died
The Day the Music Died
The Waylors