WATCH: Jelly Roll Gives Inmates a Taste of Freedom on Stage in Charlottesville

Jelly Roll’s Beautifully Broken Tour has been nothing short of an inspiring journey across the country. But at his recent Charlottesville stop, Jelly took his commitment to second chances to a whole new level, delivering a performance that few in the audience or on stage will ever forget. In a rare and powerful gesture, Jelly arranged for a group of local inmates, whom he had met earlier in the day, to join him on stage for an experience that was as raw and emotional as the lyrics in his songs.

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Jelly has always been known for visiting local jails and rehabilitation centers, bringing hope and heart to people who know hardship all too well. But after his visit to the Charlottesville jail, something remarkable happened. Inmates began singing his own songs back to him, pouring their own emotions into each word, capturing his attention and his heart. “I walked in today, and a group of men began to sing me some of my songs in a way that I’ve never heard. I began to cry and weep in this cell with all these men and women, singing their souls out,” he shared with the crowd later that night.

Moved by their voices and their spirits, Jelly left the jail unable to shake the thought of those inmates. So, he picked up the phone and called the local sheriff. “I know this sounds crazy,” Jelly admitted, “but I’ve never got a chance to see if the dream could be real. Would you please bring those inmates to this show tonight so they could see the dream?” He was willing to foot the bill for the whole thing, determined to show these men, if only for an hour, what life could be like on the outside.

Jelly’s bold request struck a chord with the sheriff, a “visionary” who went above and beyond. Not only did he agree to bring the inmates to the show, but he also honored Jelly’s special request: “Can we put them in street clothes? I don’t want them shackled and chained on stage.” True to his word, the sheriff made sure not a single chain or shackle was in sight as four young men took their places on stage. The crowd erupted, giving them the kind of welcome Jelly himself might have received on his first big tour stop.

As Jelly introduced his “newly found friends”—EJ, Fred, Kevin, and another young man affectionately nicknamed “Cali”—he made it clear that they were more than their circumstances. “These young men woke up in county jail, they’re gonna go to sleep in the county jail, but for the next hour, they get to live like us for a minute and sing a little music,” he said, voice filled with pride and passion. “If anybody believes in second chances, it’s a Jelly Roll show, right?”

To top off the moment, the group launched into a rendition of Jelly’s new song “Unpretty,” a track about finding beauty and worth where it’s least expected. Having heard the inmates’ own take on it that morning, Jelly was eager to share the song with his fans in its new, deeply personal form. The inmates didn’t just sing the words—they lived them, giving the song an intensity that the audience felt deep in their bones.

By the end of the night, Jelly had done more than give a concert. He’d offered hope, proving that music has the power to connect, heal, and even free people—even if just for an hour. His Charlottesville stop became not only a highlight of the Beautifully Broken Tour but a testament to the power of second chances, and a reminder that sometimes the most beautiful parts of a song are the voices that need to be heard most.