During his electrifying show in Virginia, Jelly Roll made an unforgettable move that had the crowd in tears—he invited inmates onstage with him! As they stood together, Jelly Roll shared a powerful message: “The future can be so much more.” -

Jelly Roll is currently on top of the world, but life wasn’t always red carpets and CMT nominations. Born Jason DeFord, the “I Am Not Okay” hitmaker cycled in and out of jail as he grappled with addiction in his late teens and early twenties. And since breaking through with his 2023 country debut, Whitsitt Chapel, the former rapper has used his platform to inspire and encourage. During a recent stop in Virginia, he showed four incarcerated men what their “wildest dreams” could look like.

Jelly Roll: “One of the Most Special Moments of My Career”

Ahead of his Oct. 30 show in Chesterfield, Virginia, Jelly Roll stopped by the Chesterfield County Jail to visit members of the facility’s HARP program.

Short for Helping Addicts Recover Progressively, HARP is a jail-based treatment and recovery program for people struggling with substance use disorder while behind bars.

The “Son of a Sinner” singer routinely stops at local jails while touring. However, this time was a little different. Jelly stepped back and let the inmates sing to him.

“I almost cried, man,” said the Grammy nominee, 39. “Watching everybody sing back to you… the opposite of addiction is connection. And this is that. People are getting sober. People are changing their lives.”

Strongly moved by his interactions, Jelly Roll had a crazy idea. He convinced the Chesterfield County sheriff to let four inmates join him onstage during his show at the John Paul Jones Arena.

The men tradeded their jumpsuits for street clothes as they performed “Unpretty” alongside the Entertainer of the Year nominee.

“Itf anybody believes in second chances, it’s a f—ing Jelly Roll show,” the singer announced just before welcoming the men onstage.

The “Need a Favor” singer summed up “one of the most special moments of my career” in an emotional Instagram post Thursday (Oct. 31.)

“My hope with bringing these men out on stage with me is that they can see a larger picture of what life can become,” he wrote. “The place they’re in now is not the end, and the future can be so much more than their wildest dreams.”