Waylon Jennings’ guitar thrummed with a defiant spirit, his Telecaster was an extension of his soul. It wasn’t about polished virtuosity, but raw authenticity, every note echoing the grit and grace of his outlaw persona. His fingers danced across the frets, weaving tales of heartache and resilience, each slide and bend etched with the dust of Texas highways and smoke-filled honky-tonks.

No pristine perfection, Waylon’s guitar sang with the imperfections of humanity, its twang a lonesome cry yearning for freedom, its bite a defiant growl against injustice. It was a sound that resonated deep, not just in ears, but in hearts, forever cementing Waylon Jennings as a legend whose guitar spoke a language far louder than any words ever could.

And that sound! That glorious sound! It was 100% Waylon, completely unique. There was no mistaking it, when you heard it you knew, as Hank Jr said, “Waylon and his Fender Telecaster that had that sound.”

On this video we’ve compiled some of his best solos, riffs and bold harmonic convergences for your enjoyment. Waylon Jennings was  a lot of things, he was the rough-hewn king of outlaw country, riding on a wave of twang and rebellion.

Waylon was a storyteller etched in steel strings, his songs the echoing cries of restless hearts.

Waylon was a voice of defiance amidst Nashville’s polish, whispering tales of grit and grace.

Waylon was a weaver of musical tapestries, where whiskey-soaked verses met the sun-bleached blues.

Waylon was a restless highwayman of harmony, forever chasing the horizon with his guitar slung low.

By John Wesley Karson

John Wesley Karson grew up in Texas in the 1960’s and 70’s and was a fan of the country music scene thriving in Austin and Houston. He first began working in radio as a teenager at KPFT in Houston, a listener supported radio station which featured many of the outlaw country artists of that time. He worked on a volunteer basis at first, cleaning up around the station, emptying trash and taking every opportunity afforded him to learn the technical aspects of running the stations equipment. Eventually he was asked to operate the control board for Jerry Jeff Walker one night when he was guest hosting a radio show. It was at that point John was hooked and he knew his future would be in broadcasting. After 45 years in the broadcasting business, working as a commercial radio disc jockey and talk show host, John Wesley Karson retired in Bakersfield in 2020. When his friend Danny Hill bought KVLI radio in Lake Isabella, California in 2021 and launched Outlaw Country Radio 103.7FM, he asked John if he would like to host a weekend show. He gave John Wesley complete creative control over the shows content and John created “The Icons of Outlaw Country”. “It’s a complete labor of love,” John said, “This is the music I grew up listening to in Texas and I just want to share it with people as a way of honoring the contributions these great artist’s made to the world.” “It’s a celebration of the individual, over the collective and the rights as free and sovereign men and women to create what first and foremost pleased them, not some record company executive occupying space in an office building in lower Manhattan or West Los Angeles. “The right of the artist to demand control of their own destiny and their own intellectual property is a sacred right and only when the artist is able to achieve this is the artist truly free to create. Music is practically the only art form where the rights of the artist are superseded by some corporate weasel in a suit and tie sipping decaf lattes from the back of a limo. “As Ayn Rand put it, a 'Right'…means freedom from compulsion, coercion or interference by other men and that applies to record companies and producers as well as governments.” John Wesley Karson had a front row seat long before the term “Outlaw Country” was even used to describe what was known at that time as the “Cosmic Cowboy” revolution. John’s radio career spanned over four decades and each week he shares music and insight into these icons of country music, taking his listeners on a two hour sonic journey through the past and into the present state of the world of country music from his studios in Bakersfield, California.