What would outlaw country be today without the late great Waylon Jennings? From his solo career to his time in The Highwaymen, few individuals are more synonymous with the outlaw country movement as Jennings.
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Throughout he career, Jennings produced a whopping 96 singles that charted on the Hot Country Singles chart, 16 of which topped that chart. A whopping 54 of his albums charted on the Top Country Albums chart as well, 11 of which made it all the way to No. 1. And he did it all without going the way of the polished Nashville sound. He was an outlaw country star and had the mindset of a cowboy, and his legacy won’t soon be forgotten.
Tragically, we lost Jennings on this day, February 13, in 2002. Let’s celebrate the icon’s legacy in country music by looking back at his storied career.
Waylon Arnold Jennings was born on June 15, 1937, in Littlefield, Texas. He learned to play the guitar at only eight years old and was influenced by the likes of Hank Williams, Elvis Presley, and others.
Jennings began performing at family gatherings in his youth before playing his first public performance at a local youth center. He had a lot of talent from the start but was also somewhat troubled in his younger years. Jennings dropped out of high school after several disciplinary infractions at 16.
From there, Jennings decided to pursue music professionally and began recording demos with The Texas Longhorns.
The Legacy of Waylon Jennings
In the late 1950s, Buddy Holly took an interest in Jennings’ music and invited him on tour. Jennings, sadly, was one of the last people to speak to Holly before he boarded a plane in 1959 that would crash, killing Holly and several others.
In the 1960s, Jennings was one of many musicians who tried to go the Nashville route with his career. He didn’t find an enormous amount of success and instead released Ladies Love Outlaws in 1972. Considered one of the earliest outlaw country classics, that album would change his career forever. From there, Jennings released 30 outlaw country albums (several posthumously) that would mark a well-lived life and career. He would join The Highwaymen in 1985 with the likes of Willie Nelson, Johnny Cash, and Kris Kristofferson.
Waylon Jennings suffered from diabetes for a number of years and battled drug use for longer, though he kicked c*caine and smoking before he passed. Sadly, he passed due to complications from diabetes in 2002 at the age of 64. He passed peacefully in his sleep at his home in Chandler, Arizona. If it weren’t for him, we likely wouldn’t have Hank Williams Jr., Steve Earle, Jamey Johnson, and more, as each has said he influenced them in a major way.
Photo by Larry Hulst/Michael Ochs Archives/Getty Images
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