Jelly Roll's Tragic Confession About His Youth Shows How Far He's Come

Fans of Jelly Roll know the "I Am Not Okay" singer has undergone a complete transformation and overcame a lot throughout his tragic life. Between struggling with mental illness and conquering addiction, one major demon he's had to face is his criminal history, which began at a young age.

As an adult, Jelly Roll was first arrested at the age of 18 for aggravated robbery, and he's also faced charges tied to his former life as a drug dealer. However, his criminal history reaches as far back as the age of 13, when he was booked for strong-arm robbery. "I'd gotten a fight with a kid and back then they had the chain wallets," he told Jay Shetty in an October 2024 episode of the "On Purpose with Jay Shetty." "When we were wrestling, I grabbed a chain wallet to try to hit him with it, and that was a strong-arm robbery case. So I ended up in the system for like 20-something months when I was 13 for that strong-arm robbery."

Regarding why his life took this route, Jelly Roll said his poor self-esteem drove him to be more aggressive. "It's deep-rooted insecurities early," he told Shetty. "I was always a bigger kid. So I had a little chip on my shoulder naturally as a young kid." Throughout his career, Jelly Roll has been open about his insecurities and mental health issues, which he's channeled into his music.

Although Jelly Roll was the force behind all these past aggressions, he's since looked back on his youth with a deep sense of regret. "I look back at those years, Jay, and I'm so embarrassed to talk about them," he told Jay Shetty. "I was still a bad person in my early 30s, but I mean, I was a really horrible kid all the way into my mid-20s. People are always like, 'You're the nicest dude I've ever met.' I'm like, 'I'm so glad y'all haven't met nobody that knew me 20 years ago.'"

Keeping his troubled past in mind, Jelly Roll has described his saving grace as the moment his daughter, Bailee Ann DeFord, was born. At the time, Bailee, who was once apprehensive about, but has since embraced, her dad's fame, made her grand debut while her father was serving time. Her birth provided a wakeup call to Jelly Roll, who accepted the news as the motivation to get his act together. "In that moment, I made a promise with her that I had to be there for her," he said in the documentary "Jelly Roll: Save Me" (per Hollywood Life). "It's almost like something clicked right then."