Caleb Montgomery on Country Music News International Radio Show!
February 14th interviewed by Big Al Weekley for Country Music News International Radio Show
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The Cowboy with a Hundred-Year-Old Soul: The Rise of Caleb Montgomery
By Christian Lamitschka for Country Music News International Magazine
In an era of country music often defined by polished production and pop-leaning hooks, Caleb Montgomery is a breath of sagebrush-scented air. Hailing from the rugged cattle country of Susanville, California, Montgomery has rapidly emerged as a powerful new voice in the neo-traditional and Americana scenes. With a vocal delivery that feels both raw and seasoned, he is proving that the most resonant stories are often the ones told with a simple guitar and a truthful heart.
Roots Run Deep in the High Desert
Montgomery’s connection to music isn’t just a career choice; it’s a family legacy that spans six generations. Growing up in northeast California, near the Nevada border, he was immersed in a world of ranching, rodeos, and rural tradition. His father, Chris Montgomery, was a country artist in the 1990s who performed at the legendary Ryman Auditorium alongside icons like Willie Nelson and Kris Kristofferson.
Though Caleb had a guitar in his hands by the age of five, his path to the stage wasn’t immediate. He spent his youth focused on the cowboy lifestyle his parents fought hard to provide—a life of horses, hard work, and the “Cowboy Creed,” a set of guidelines his parents gave him to teach him how to treat others with respect and integrity.
From the Dorm Room to the Billboard Charts
The turning point for Montgomery’s music career came unexpectedly while he was away in Nebraska on an athletic shooting scholarship. Feeling isolated and homesick, he turned to songwriting as a form of therapy. “I just spilled how I was feeling onto the paper,” he recalls. Soon, students would gather in the hallway outside his dorm room just to hear him play.
This period of “dorm room therapy” birthed the honest, narrative-driven style that defines him today. Upon returning to California to finish school, he reunited with his brother Joshua—a talented multi-instrumentalist who now plays fiddle, mandolin, and guitar in Caleb’s band. Together, they began crafting the sound that would eventually catch the ear of Nashville-based Label22 Records.
“Food Stamps Don’t Buy Flowers”
In late 2023, Montgomery released his debut single, “Whiskey Talks,” a ballad that captures the vulnerability of young men in the rodeo and ranching community. The song struck a chord for its authentic portrayal of “well-mannered cowboys” sharing their pipe dreams and struggles at the bottom of a bottle.
His debut album, Food Stamps Don’t Buy Flowers, released in 2024, further solidified his place in the industry. The title track and other fan favorites like “Ponderosa Pines” and “Blue Eyed Bandit” showcase a songwriter wise beyond his years. The album’s success led to a Billboard-charting release and a standing-room-only release party in his hometown of Susanville, where he used the event to raise funds for local scholarships.
A Modern Troubadour’s Mission
Caleb Montgomery’s music is a bridge between the old West and the modern world. Drawing inspiration from legends like Conway Twitty and contemporary truth-tellers like Tyler Childers and Sturgill Simpson, he crafts songs that resonate across generations. Whether he’s singing about the “Speed of Sound” or the quiet dignity of a working-class life, his mission remains the same: to show people they aren’t alone in their struggles.
As he moves into 2025, Montgomery is expanding his reach from the California fairground circuit to the historic stages of Nashville. Yet, despite his rising fame, his heart remains firmly planted in the high desert. He continues to live the life he sings about, proving that in the world of country music, nothing beats the truth.