waylon n willie

Waylon Jennings (R) with fellow outlaw Willie Nelson (L)

On this day in 2002, the country music outlaw Waylon Jennings died aged 64. It wasn’t a huge surprise to most who knew him. He had been a smoker, drinker and drug user for a long time. He eventually gave up his vices, but it was too late.

Jennings was born in 1937 in Texas, and began playing music at the age of eight. By the time he was twenty-one he had been hired to play base for Buddy Holly. At this point, you would have been forgiven for thinking that Jennings was on the way to the big time, fate had other ideas. After a show in Iowa, Buddy Holly chartered a plane to take them to the next venue. Upon learning that The Big Bopper (JP Richardson) had come down with a cold, Jennings offered his seat up and drive instead. History tells us that Jennings made it to the next venue, and Buddy Holly, The Big Bopper and Richie Valens all perished when the plane crashed. The music died for many people that day, not least Jennings who went on to work as a DJ, feeling immense guilt at the crash.

waylon n buddy

Waylon Jennings (L) smoking it up with Buddy Holly (R)

Jennings couldn’t seem to find a foot hold in the sixties, but did manage to release his debut album ‘Folk-Country’ and a hit single ‘Just To Satisfy You’. It was the 1970’s that were to prove the turning point for Waylon as he joined the outlaw country movement along with friends like Willie Nelson, and later, Johnny Cash and Kris Kristofferson. The basis of this movement was the artists unhappy with the Nashville producers who insisted on using session musicians rather than the artists own band. Under these conditions, Jennings wasn’t allowed to play his own guitar or select the music he wanted to record. It even went as far as having to dress in a certain way. The artists decided to go their own way, resulting in Jennings album in 1972 entitled Ladies Love Outlaws.


Waylon followed this up, in 1973 with his best album the stone wall outlaw country classic, Honky Tonk Heroes. This was followed up by The Ramblin’ Man in 1974. It was around this time that Jennings drug intake began to get out of control. It started in the 1960’s with amphetamines before cocaine was introduced in the seventies. It came to a head in 1977 when Jennings was arrested for possessing cocaine. A courier had warned the DEA about 27 grams of cocaine that had been sent to Jenning’s recording studio. By the time the DEA had arrived and searched the place Waylon had flushed the cocaine down the toilet. He was subsequently released without charge.

Into the 1980’s and Jennings coke habit increased to such an extent that he was sending $1500 a day, resulting in debts of $2.5 million. He ultimately ended his habit in 1984 and went on to record some hugely successful albums as The Highwaymen with his pals, Willie Nelson, Johnny Cash and Kris Kristofferson. He also recorded the famous theme tune to eighties TV show Dukes of Hazzard, and appeared in several episodes.

By the end of the nineties however, his health was catching up with him. Diabetes meant he could no longer tour, and in 2001 the illness resulted in his foot being amputated. In 2002 his lifestyle in the proceeding decades took it’s toll and he died in his sleep from complications due to diabetes.

It seems, looking back on his life that Waylon Jennings may have had more than one life anyway. Fate took care of him back in the fifties, and all throughout the next two decades. He came out the other side as a bona fide legend with an impressive musical legacy and a reputation as an outlaw. Not bad for someone who should have died in a plane crash with Buddy Holly.


About thomasjford

I like Movies and Music and most things popular culture.


  1. Interesting post, he sure looked like he had an eventful life.

  2. Thanks for this reminder, Tom. 12 years already?! Tempus fugit.

  3. Amazing all the drugs. And complications from said drugs. Reminds me a lot of the Slash autobiography that I’m reading at the moment!

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