Waylon Arnold Jennings ( pronounced ; June 15 , 1937 – February 13 , 2002 ) was an American singer , songwriter , and musician . In 1958 , Buddy Holly arranged Jennings 's first recording session , and hired him to play bass . Jennings gave up his seat on the ill-fated flight in 1959 that crashed and killed Holly , J. P. " The Big Bopper " Richardson and Ritchie Valens . During the 1970s , Jennings was instrumental in the inception of Outlaw country movement , and recorded country music 's first platinum album , '' Wanted ! The Outlaws '' with Willie Nelson , Tompall Glaser , and Jessi Colter
crashed and killed
The Day the Music Died
Waylon Jennings