Waylon Jennings ( June 15, 1937 – February 13, 2002) was a respected and influential American country music singer and guitarist, born in Littlefield, Texas.
Growing up in the abject poverty of the Dust Bowl, a young Waylon Jennings sought to escape the dirt roads of Littlefield. He began singing at an early age, winning a spot singing and playing guitar on a local radio show. He became a popular DJ for several Texas radio stations, and a musical performer on the early rock and roll performance circuit in Texas, alongside the likes of fellow Texans Roy Orbison and Buddy Holly. In 1956, he married Maxine Lawrence.
After Holly achieved national stardom, he offered to produce Waylon's first records. Though neither of the first two recordings had much success, it was the beginning of a short but influential friendship with the rockabilly legend. Holly asked Waylon to join his touring band playing bass guitar, an offer Waylon accepted despite the fact that he did not know how to play bass. They embarked on a nationwide tour riddled with difficulties, including a tour bus without heat that repeatedly stalled in the cold weather.
On the night of February 3, 1959 ( The Day the Music Died) the airplane carrying Buddy Holly, Ritchie Valens and J.P. Richardson (aka The Big Bopper) crashed outside of Mason City, Iowa, killing all passengers. Waylon had given his seat to Richardson, who had the flu and desperately needed rest. In his 1996 autobiography, Waylon admitted for the first time that in the years afterward, he felt severe feelings of guilt and responsibility for the crash. After Waylon gave up his seat, Holly had jokingly told Jennings that he hoped the tour bus would stall. Jennings replied, with equal jocularity, that he hoped the plane would crash; these words would haunt him for years.