Roll opens up about his troubled past, time in jail, and how he turned his life around.
Country music star Jelly Roll recently talked about his difficult past and how he’s working to become a better person on the podcast On Purpose with Jay Shetty. The 39-year-old singer shared stories about his early life, his time in jail, and the ways he’s trying to make up for his mistakes today.
Jelly Roll, whose real name is Jason DeFord, grew up in Antioch, Tennessee. As a kid, he struggled with being different. “I was always a bigger kid,” he said. This made him feel insecure, and it caused him to develop a “chip on his shoulder.” He found acceptance in the streets of his neighborhood, which led him down a rough path. “The streets will always give you acceptance,” he explained, talking about how easy it is to fall in with the wrong crowd when you’re looking for a sense of belonging.
At just 13 years old, Jelly Roll found himself in serious trouble. He was involved in a fight with another kid, and in the middle of the scuffle, he grabbed the boy’s chain wallet. Trying to use it as a weapon, Jelly was charged with strong-arm robbery and sent to jail for almost two years. This early encounter with the legal system set the tone for what would be a difficult period in his life.
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“I’m so embarrassed to talk about those years,” Jelly Roll admitted. “I was a really horrible kid all the way into my mid-20s. Even in my early 30s, I wasn’t a good person.” While today people describe him as one of the nicest people they’ve met, Jelly Roll knows it took him a long time to get there. “I’m glad y’all haven’t met anyone who knew me 20 years ago,” he said, hinting at how different he used to be.
One thing Jelly Roll is working on now is making amends with the people he hurt in the past. He explained that he has a list of people he needs to apologize to, including the victim of that robbery when he was 13. “I haven’t made it that far down the list yet,” he shared. “I had no business taking from anybody, no matter how old I was.” He now realizes that his sense of entitlement—feeling like the world owed him something—was wrong.
Family has played a big part in helping Jelly Roll turn his life around. He had a strong bond with his father, who passed away in 2019. After breaking free from the cycle of getting in and out of trouble with the law, Jelly and his dad grew even closer. They spent time together regularly at a place called the Tin Roof in Nashville. “We’d go to happy hour three or four days a week, from 4 to 6,” he said, cherishing those memories with his father.
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His mother also had a significant impact on him, although her struggles with drug addiction and mental health made their relationship challenging. “She became really reclusive,” he said. “For about 20 years, I rarely saw her out of a nightgown.” But music became a special way for them to connect. “When she seemed her healthiest, there was always music playing,” he said. His mom would call him up to read the lyrics to the songs he was writing, and those moments stayed with him.
Today, Jelly Roll is a father himself and hopes to set a good example for his two children, Bailee Ann, 16, and Noah, 7. Speaking about his daughter, he said, “She’s going to be everything I wasn’t in life.” He’s also done a lot of personal work to forgive himself for the mistakes he made in the past. “I didn’t cry until I was 33,” he revealed. “Now I can’t stop. Sometimes I’ll just sob for no reason.”
Music has been an important part of Jelly Roll’s transformation. He recently won a People’s Choice Country Award for his song “Lonely Road,” a collaboration with rapper mgk. They reimagined John Denver’s classic “Take Me Home, Country Roads” in a way that connected with a new generation of listeners. Fans can catch Jelly Roll on his Beautifully Broken tour, which will finish on October 27 in Charlotte, North Carolina.
