Country Stars Who Traded Jail Time for Stardom

By: Brian Zwerner

Apr 15, 2025

Nashville's path to fame isn't always paved with gold records. For some of country music's notable names, it involved detours through the justice system. While fans know their hits, the backstories of several stars include surprising chapters featuring reform schools and jail cells.

Take David Allan Coe, an undisputed "outlaw" legend. His troubled youth began early, landing him in reform school at just nine years old. Coe spent roughly two decades cycling in and out of correctional facilities. It was during one stint inside that he reportedly met fellow musician Screamin' Jay Hawkins, who encouraged him to pursue singing. Fittingly, Coe's debut album was titled Penitentiary Blues, cementing his hard-earned outlaw image.

More recently, Trey Lewis found his footing after a rocky start. By 19, he had already faced time in jail and psychiatric wards. Hitting bottom proved a turning point. Lewis got sober and, while living in a halfway house, taught himself guitar. Now, he's known for bringing humor and a raw edge to country with hits often described as raunchy and funny. A testament to a second chance embraced.

Perhaps the wildest journey belongs to Jelly Roll. His encounters with the law started at 13, leading to an estimated 40 arrests and significant time behind bars. The catalyst for change came dramatically with the birth of his daughter while he was incarcerated. Determined to turn his life around, he found initial success in hip-hop before making a massive crossover into country music. His raw honesty resonated, earning him the CMA Award for Best New Artist and even a Grammy nomination, proving redemption songs aren't just for the airwaves.

© Country Bios 2025

© Country Bios 2025

© Country Bios 2025