Credit: Alamy

Waylon Jennings: The outlaw who cheated death

The early hours of February 3rd 1959 were witness to one of the most gruesome events in music history – what later came to be known as ‘The Day the Music Died‘. Buddy Holly, Ritchie Valens and J. P. Richardson were on Holly’s Winter Dance Party tour across the Midwest but the hectic schedule, haphazardly picked venues, awful weather conditions and the extensive distances the band had to travel, along with the complications with the tour bus, soon caught up with them.

Frustrated and tired, Holly booked a flight from Clear Lake, Iowa, to their next show venue in Moorhead, Minnesota to cut the travel time short. But, little did they know what fate had in store for them. The flight never made it to its destination, crashing into a cornfield barely six miles away from where it took off, killing all four onboard – Holly, Valens, Richardson and the pilot Roger Peterson.

At the time of the Winter Dance Party tour, Holly and his band, consisting of Waylon Jennings, Tommy Allsup and Carl Bunch, were accompanied by rising artists such as Richardson and Valens as guests. Many in the group, affected by the long uncomfortable journeys on the tour bus and the freezing temperatures, were suffering from cases of flu and frostbite. It was then that Holly decided to charter a plane to reach the next venue relatively comfortably. The plan was that the band members were going to board the plane to reach their destination. But, Allsup lost his seat to Valens in a coin-toss, while Jennings gave his seat up to Richardson who was suffering from the flu, thereby making Allsup and Jennings the survivors of a plane crash they were never on.

Jennings later revealed a part of a conversation that he and Holly shared when the singer learnt that Jennings was not going to board the plane. In jest, Holly had said: “Well, I hope your ol’ bus freezes up” to which Jennings had countered, “Well, I hope your ol’ plane crashes” – a response that continued to haunt him for the rest of his life.

Waylon Jennings, who learned of the plane crash on the news, called his family and the KLLL’s Sky Corbin to let them know he hadn’t boarded the plane. Arrangements were later made to complete the Winter Dance Party tour, which now featured Jennings as lead singer, and it continued for another two weeks. Jennings went on to write and record ‘The Stage (Stars in Heaven)’ in the 1960s as a tribute to Holly, Valens and Richardson as well as Eddie Cochran, a musician who died in a road accident a year after the plane crash.

For years, Jennings held himself responsible for what happened to his band members and resorted to substance abuse, as a means of escape, through much of his career. Jennings’ career went through a wave of turmoil and for nearly a decade as he struggled to find solid ground as an artist. He switched from one record company to another in hopes of better opportunities. In 1972, he released his album Ladies Love Outlaws.

This album marked Jennings’ transition towards his outlaw country image and style. Jennings was one of the pioneer artists to secure outlaw country as a rising musical genre. The music was defined by honky-tonk and rockabilly, fused with folk rhythms, country music and introspective lyrics that focused on the law-opposing lifestyle. It originated as a kick against the controlling nature of the Nashville sound, which Jennings himself experienced. With the release of Wanted! The Outlaws, a compilation album featuring Jennings, Willie Nelson, Jessi Colter and Tompall Glaser, in 1976, outlaw country gained widespread recognition.

Outlaw music embraced everything that resisted the mainstream. From shedding the “proper” garb to countering the orthodox Nashville sound, to espousing an independent, non-conformist approach to music — outlaw country soon gained popularity as a subgenre of country music. Waylon Jennings was regarded as one of the movement’s spearheads; his history of standing up to his record company and forcing them into letting him play his own sound, making him the ultimate embodiment of all things outlaw.

Jennings went on to produce several more albums such as Lonesome, On’ry and Mean, in 1973, followed by Honky Tonk Heroes. As the movement evolved, Jennings began to feel restricted by the outlaw style as well, referring to the overexploitation of the outlaw image in his 1978 song ‘Don’t You Think This Outlaw Bit’s Done Got Out of Hand’. Jennings would go on to produce several singles and albums throughout his career. His Never Say Die: Live (2000) became his final album, which was recorded in Nashville’s historic Ryman Auditorium that played a pivotal role in popularizing country music.  

After a long battle with excessive smoking, drug abuse, diabetes and heart issues, Waylon Jennings died from diabetic complications in his sleep in 2002. His music had a huge impact in changing the course of music, blending different styles and forms taken from different genres and bringing it under one umbrella. He influenced several artists after him and brought about a revolutionary change in how music would be and should be perceived.

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