Waylon Jennings Biography

Waylon Jennings is a Texan legend when it comes to musical expression and songwriting. Born in Littlefield, Texas, USA on 15 June 1937, Waylon Jennings went on to have an extensive and ground-breaking career which included not only songwriting for which he received multiple awards but also saw him taking on acting work as well.

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Waylon Jennings was tutored from a young age to enjoy music. Learning his first musical lessons from his mother at the age of eight, it was not long before he was playing borrowed guitars at family gatherings. He continued to borrow guitars from any family member who had one until he was gifted with a used Stella guitar from his mother. She later replaced this old Stella with a Harmony guitar.

Waylon’s talent did not go unnoticed – between serenading his family and winning talent shows, he set his sights on something bigger and auditioned to play on the local Littlefield radio station, KVOW. Waylon was only 12 years old at the time but the owner of KVOW, J.B McShan, was not put off by the age of this new performer and liked what he heard. He ended up bringing on Jennings for a weekly 30-minute program, and Waylon took the opportunity to collect some of his other musically gifted friends and acquaintances together to form his first band, the Texas Longhorns.

From the age of 12 and through high school, Jennings grew his musical talent and ability but he was also disruptive and unruly at school and so at the age of 16, the local high school superintendent excluded him. Being forced out of school led Waylon to start looking for work and he went through a variety of jobs, including driving a concrete truck, working for a lumber company, and working in produce at a grocery store, but through all of this, it was his music and the desire to make music his career that kept him going.

While performing on KDAV Radio, Waylon Jennings met Buddy Holly and the two became fast friends. Continuing his music career working as a DJ in Lubbock, Texas, Jennings recorded a variety of songs that would become some of his most iconic pieces. Some of the music produced during this time included songs like “Jole Blon” and “When Sin Stops (Love Begins).”

It was in 1958 that Waylon Jennings’ fortunes began to change when he was invited by Buddy Holly to go on what would become the now infamous Winter Dance Party tour.

The Winter Dance Party tour began on 23 January 1959, in Milwaukee, Wisconsin. However, scheduling was not given enough thought, considering the distances and difficulty of winter travel in the Midwest. The tour buses broke down repeatedly, even leading to a frostbite related hospitalisation of the band’s drummer. This led to the need to make other travel arrangements. Renting a charter plane to get to their next location of their next gig seemed to be the best way, although the plane would not seat everyone. Waylon Jennings gave up his seat to a fellow tour member who had the flu. It was during this time that an incident occurred that would haunt Waylon for the rest of his life.

When Buddy Holly found out that Waylon had given up his seat on the plane and was going to take the bus to the next venue location, Buddy Holly is reported to have said, “I hope your butt freezes,” to which Waylon jokingly responded, “Well, I hope your plane crashes”. A few hours later on 3 February 1959, that is exactly what happened when the plane carrying Buddy Holly, and other musicians at the start of what promised to be massive careers,  crashed in Iowa, killing all on board. Waylon Jennings felt personally responsible for having joked about such a thing before his friend’s death and this led to chronic substance abuse throughout much of the rest of his career.

It was during the mid-to-late 60s that Waylon Jennings’ music really came into it...