Sturgill Simpson is a modern-day musical gunslinger, blazing a trail through the heart of American music with his electrifying blend of outlaw country, bluegrass, rock, and touches of psychedelia. Here’s a glimpse into his world:

Roots & Rise: Born in Jackson, Kentucky, in 1978, Simpson was steeped in Appalachian music from a young age. He honed his skills on guitar and banjo, later joining bands like J.D. Wilkes & the Dirt Saints and Tyler Childers’ backing band. In 2013, he embarked on his solo journey, quickly grabbing attention with his raw authenticity and genre-bending spirit. The first song on his first album, “Life Ain’t Fair and the World Is Mean” let you know, Sturgill Simpson was redefining outlaw country.

Outlaw Spirit: Simpson’s music is infused with the rebellious spirit of outlaw country pioneers like Waylon Jennings and Willie Nelson. He challenges Nashville’s conventions, singing unapologetically about blue-collar struggles, heartbreak, and the search for truth. Songs like “Listening to the Rain” and “Long White Line” resonate with their gritty honesty and soulful vocals.

Musical Adventurer: Simpson isn’t afraid to push boundaries. His albums showcase diverse influences, from the rootsy stomp of songs like, “You Can Have The Crown” to the psychedelic exploration of an album like, “A Sailor’s Guide to Earth.” He collaborates with artists from different genres, like Fiona Apple and Tyler Childers, always seeking new ways to express his artistic vision.

Live Powerhouse: Seeing Sturgill Simpson live is an unforgettable experience. His band, The Moonlight Riders, whips up a musical storm, while Simpson delivers his songs with an intensity that can crack open your soul. His live shows are full of raw energy, improvisation, and moments of pure musical magic.

Impact & Legacy: Whether he’s performing his originals or cover versions of John Prine songs like, “Paradise”, Sturgill Simpson is revitalizing country music for a new generation. He’s earned critical acclaim, Grammy awards, and a loyal following of fans who are drawn to his uncompromising honesty and musical adventurousness. His impact is undeniable, solidifying his place as one of the most important and exciting voices in contemporary music.

The Concept Album: The Ballad of Dood & Juanita by Sturgill Simpson isn’t just an album – it’s a dusty, smoke-soaked tapestry woven from outlaw country, Appalachian bluegrass, and gospel whispers. Released in 2021, it’s a concept album set in Civil War-era Kentucky, and it tells the heart-wrenching tale of Dood, a sharpshooting mountain man, and Juanita, his fiery love.

Simpson throws genre expectations out the window. One minute, you’re stomping to the banjo-driven bluegrass of “Ol’ Dood (Part I),” the next, you’re lost in the soulful ballad of “Juanita” (featuring Willie Nelson himself), your heart aching alongside Dood as he searches for his kidnapped love. It’s raw, it’s honest, it’s steeped in the traditions of mountain music while pushing its boundaries with psychedelic flourishes and gospel harmonies.

The story unfolds like a campfire yarn, each song a flickering flame illuminating the next. We hear Dood’s bravado in “Shamrock,” his desperation in “One In the Saddle, One On the Ground,” and his unwavering love for Juanita in the gospel-tinged “Go In Peace.” It’s a story of resilience, of love defying even the darkest times, and it’s all delivered with Simpson’s powerful vocals and an ace band known as the Hillbilly Avengers.

“The Ballad of Dood & Juanita” is more than just a love story. It’s a snapshot of a time and place, a tribute to the enduring spirit of Appalachia, and a testament to the power of music to transport us to another world. It’s an album that lingers long after the final notes fade, leaving you humming melodies and pondering the depths of human love and loss.

We’ve barely cracked the code of Sturgill Simpson’s artistic puzzle in this article. Each song you hear will unlock a brand new layer of his musical depth and lyrical soul, so dive deep. Whether you’re a seasoned listener or a curious newcomer, his music rewards exploration. Sturgill Simpson’s music isn’t just entertainment, it’s an entire experience. His blend of craft, depth, and energy leaves a lasting impression, resonating with both hard core country buffs, Americana fans and casual yet adventurous newcomers.

My plan for world peace and harmony is that everyone should listen to at least one Sturgill Simpson song every day.

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.