Following the break-up of The Crickets, Jennings played bass for Buddy Holly.
During a particularly harsh winter in February 1958 while touring with Holly, Ritchie Valens and The Big Bopper, 21-year-old Jennings offered up his seat on a chartered light aircraft to a flu-ridden Big Bopper, volunteering to travel in the freezing tour bus in his place.
As they were departing, Holly joked to Jennings that he hoped the coach would stall during the night. Jennings wrote in his autobiography how his quick-witted response, “I hope your plane crashes”, haunted him for years.
The plane crashed minutes after take-off, killing all three artists onboard and the pilot.
Jennings then played bass on the West Coast until 1965, when he began working the trenches for RCA in Nashville. Recording albums in the studio system left him unsatisfied though, and in 1973 he took on the mantle of producer for his album, Honky Tonk Heroes, one of country music’s landmark albums.
For writing duties, Jennings enlisted Billy Joe Shaver, a 34-year-old Texan who was just beginning to make a name as a Nashville songwriter. The collaboration proved to be an inspired one – Shaver wrote or co-wrote all but one of the album’s ten tracks, and his bleak parables of lawlessness and wantonness were the perfect match for Jennings’ low, weary singing voice.
With Jennings at the controls, the album had a stripped-down sound that was uncharacteristic of Nashville records at the time – he gave songs languorous tempos, while Ralph Mooney’s pedal steel was mournful and evocative.
As a member of the country supergroup, The Highwaymen, Jennings was overshadowed by Johnny Cash, Kris Kristofferson and Willie Nelson.
