What Jelly Roll's Time In Prison Was Really Like

Singer-songwriter Jelly Roll, aka Jason DeFord, continues to excel. From winning three CMT Music Awards two years in a row, to having a No. 1 song on multiple charts simultaneously, things are looking up for the rapper. However, that hasn't always been the case.

Jelly Roll had a tough childhood and found himself in trouble with the law at a young age. His first arrest happened at the tender age of 14 and was drug-related, followed by a second and third arrest for robbery. He served time at Nashville's Davidson County Juvenile Detention Center for those crimes, but life got a whole lot worse when he was charged as an adult at only 16 years old for aggravated assault.

From then on, Jelly Roll was in and out of prison until he was 24, once dubbing himself "the worst criminal ever." Now that he's cleaned up his act, Jelly Roll revealed what being incarcerated was really like, from the scary moments to the beneficial lessons.

During an interview on "The Howard Stern Show," Jelly Roll explained that when he was dealing drugs on the street, the street didn't have any rules; anything could happen and nothing was safe. But in prison, there was "a sense of safety there" and you could allow yourself to dream about ways to turn your life around.

Moreover, Jelly Roll's time was mostly spent in state prisons, not federal ones, so he didn't really experience the gang violence typically associated with lockup. He explained how inmates all knew one another, calling it "kind of cool." But he did mention fights still broke out — there was no getting around fighting in prison; it was just a part of the life. A fight could happen for the smallest infractions, such as spitting in the sink, which is what happened to Jelly Roll with his cellmate. The musician was punched in the face and when he later asked why they were even fighting, his cellmate explained it was about disrespecting his space, which Jelly Roll didn't realize he was doing. Over the years, Jelly Roll estimated he "had a 70-30 record" of fights won.

He also got his first face tattoo in prison, which he admitted on "The Bobby Bones Show" wasn't the safest choice to make, but considering everything else happening around him, it was "the safest thing there."

Jelly Roll has two children, daughter Bailee and son Noah, and the musician had to learn about his daughter's birth while he was still behind bars. At 23 years old, Jelly Roll became a father, but he couldn't meet her until her second birthday. "I've never had nothing in life that urged me in the moment to know that I had to do something different. I have to figure this out right now," he told Billboard in June 2023. Bailee's birth encouraged Jelly Roll to turn his life around.

Thankfully, Jelly Roll has a great relationship with his kids, but that wouldn't have happened had he not decided to make some major life-changing decisions, like getting permission to transfer out of the violent offenders unit to the education unit where he studied for and obtained his GED.

During his time in prison, Jelly Roll wrote several songs, having to get creative with sound because he didn't have a musical instrument. "We would have to make [the music] on a table," he explained on "Jimmy Kimmel Live," demonstrating the technique by pounding on the host's desk to a beat. From there, he was eventually released from prison and able to become the successful musician fans know and love today.