What Jelly Roll's Life In Prison Was Really Like

It's taken a long time for rapper-turned-country singer Jelly Roll to get to the present. Long before he spent 28 straight weeks atop Billboard's Emerging Artists Chart with "Son of a Sinner," he was living out of his van. From 2010 to 2015, he drove and lived wherever he could make money, sometimes making just $50 or so for selling rap verses. He did this, he told Billboard, because he was "petrified" of the alternative, i.e., "sitting idle" and winding up right back where he'd lived on and off for 10 years: prison.

Born Jason Bradley DeFord in 1984 in Nashville, Jelly Roll had his first run-in with the law at age 14. By his own estimate, he's been to jail about 40 times, mostly for petty robbery and drug charges. One time, though, he landed behind bars at age 16 for aggravated robbery. "I was charged as an adult years before I could buy a beer, lease an apartment, get a pack of cigarettes ... I feel like the justice system at that point kind of parked me on my only set path," he told Billboard.

That path was full of as much fear as it was prison rules and food mash-ups like "ghetto dope," Jelly recounted to Taste of Country. It also led him to present, where despite his success he considers himself a "broken man," per The Guardian, whose music "represents so many people that haven't felt heard."

In 2023, Jelly Roll told Billboard, he was baptized at Nashville, Tennessee's Whitsitt Chapel Baptist Church around 20 years ago. [I have] since done nothing but go to prison, treat a bunch of people wrong, make a lot of mistakes in life, turn it around, [then] go on to be a f****** multimillionaire and help as many people as I possibly can," he said. The name of that church, Whitsitt Chapel, titles Jelly's hit 2023 album of the same name. It serves as a reminder of the "seed of a higher power" that carried him through prison and took him to the present.

Barring a couple of exceptions and despite all the prison tattoos across his body, Jelly speaks less of day-to-day prison life and focuses more on who he was while he was there. Speaking to Billboard, he called himself a drug runner who wanted money and a drug user hooked on cocaine, codeine, and pain pills. He said things like, "98% of every problem in my life I caused," "I was a less-than-desirable human in that era," and, "I think God forgave me way faster than I forgave myself."

When he left prison for the last time at 24 years old, he might've gone straight back if not for the news he received from a prison guard: "DeFord, you had a kid today," per CBS News. The birth of his daughter Bailee Ann was a turning point for him, and a chance to break the cycle of drugs, prison, and abandonment.

While behind bars, Jelly Roll fell into the same trap as many other inmates, where prison life became more familiar than life outside. "Prison or jail or juvey or whatever becomes more of a home than your home," he told "The Howard Stern Show." "There's a sense of safety there." He not only said it felt like a safer, less "wild card" alternative to his pre-fame existence, but that it was also more predictable than his current, musical celebrity life. But regardless of the reassurance afforded by prison structure and predictability, it was the kind of experience that was ultimately very harmful.

And yet, it wasn't all doom and gloom, at least when it came to food. Taste of Country recounts some of Jelly's favorite makeshift behind-bars food options. One of those recipes was the "ghetto dope" we mentioned earlier, comprised of pulverized, semi-water soaked Flamin' Hot Cheetos topped with mysterious "little beef sticks" and smothered in cheese. Another recipe involved smashing together Grandma's cookies, a Moon Pie, and a Snickers bar and nuking them in a microwave.

Thankfully, Jelly's left these concoctions behind, much like the rest of prison life. "That stuff is bad luck," he told Taste of Country. "I believe what's in jail stays in jail, you know what I'm sayin'?" On a related and serious note, Jelly described to Billboard confronting "demons" that included the trauma that fuels his obesity.

Despite prison affording some measure of predictability and structure — and questionable food options — Jelly Roll on "The Howard Stern Show" talked about how it's also a place of "drama" and violence. This was a rare time where he provided a window into the daily goings he experienced behind bars. 

No matter that America's state prisons can be full of familiar faces, he said, "there's no getting around a physical altercation." Earning respect is critical, and if you want to earn it, you're going to have to "fall into a cell and put your hands up." Such violence wasn't completely rash, but often strategic in nature and happened in chambers not monitored by cameras. He recounted prison guards being fully aware of such fights, but letting them play out so long as "nobody's getting stabbed or killed right now." 

Jelly told one story to Howard Stern, in particular, that really stands out. One of the first times he was in adult prison, he said, he did something as commonplace as spit in the sink in his cell. His cellmate immediately struck him, and the two started brawling. As soon as he could manage to talk, Jelly explained, his inmate told him that the sink in their cell was "sacred." It was a place to store ice and mix drinks. It was a place to store hot water. It was a place to prepare food, even pound honey buns. This story helps explain not only where Jelly came from, but prison life, in general.

Even though Jelly Roll hasn't been in prison since he was 24 years old (he'll be 40 years old in December 2024), his time spent behind bars not only haunts his soul but actually limits his legal rights, as he Billboard explains. His aggravated robbery at 16 years old is enough to prevent him from voting in Tennessee, volunteering at many non-profits, and owning a gun, and it even hindered him getting a passport until a short time ago. But even though he has a passport and can legally leave the U.S., other nations won't let him into their borders because of his criminal record. This is why he had to cancel his debut London show.

On top of these restrictions and despite his millions (he's worth about $12 million as of this writing), Jelly has had trouble buying a home. "My money was welcome, but I wasn't, all because of something I did [almost] 24 years ago," he told Billboard. He's come quite a long way from his drug-dealing prison days, to the point of having taken up golf and wanting to live in a community that has its own course. But in Tennessee, at least, it doesn't seem likely that will ever happen.

Nonetheless, Jelly continues to make himself a better man, involve himself in his children's lives, and separate from his former life. "I want to be a guidepost of hope for people to know that losers can win," he said to Billboard. "That who you were isn't who you are."