No one knows more than Jelly Roll how different his life could have turned out. The Nashville native spent more than a decade in and out of the prison system, where he might still be if he didn’t decide to turn his life around. Keep reading to find out more about one of country music’s biggest success stories.

1. He went to prison the first time at age 14 — the same year he was baptized.

Jelly Roll, whose real name is Jason DeFord, first went to prison when he was 14, for theft charges. It was, perhaps ironically, also the same year he was baptized. Jelly Roll experienced a full-circle moment when he then watched his daughter, Bailee, get baptized when she was 14 years old, with her baptism inspiring his entire Whitsitt Chapel album.

“I had started thinking about where I was at when I was 14,” Jelly Roll told Grammy.com. “I’m going to a little church, too, on a little back road on a hill, there’s just these little parallels. Bailee experienced and dabbled in marijuana for the first time, I caught her recently. Around the same age, I was dabbling in marijuana and trouble. It was just reflective. And then you start thinking about redemption. Outside of religion, the idea of being able to be redeemed is just a great idea … At that moment, I was like, ‘I want to write a conceptual album, that kind of outlines my journey of religion, my journey of spirituality, my journey of redemption, my journey of wrongdoings.’

“[It’s] my take on all these things from a 14-year-old kid getting baptized at Whitsitt Chapel to the 39-year-old man that just watched his 14-year-old get baptized,” he added.

2. His mental health struggles led him to commit crimes.

Jelly Roll firmly believes that if he had had treatment for his undiagnosed mental illness, he would have made better choices, instead of spending time incarcerated.

“I would have realized that my need for acceptance stemmed from feeling like I wasn’t good enough,” Jelly Roll said on Audacy’s I’m Listening podcast. “I felt like nobody accepted me…When you feel like nobody accepts you, there’s always that one group that will and it’s always the trouble. I feel like I might have made some crazy different life decisions if I could have sat down and felt vocal enough to say, ‘Hey, I’m leaning towards this because I don’t feel accepted anywhere else.’”

3. He met his now-wife Bunnie (who goes by Bunnie XO) in 2015, while he was performing.

Far from being a superstar, Jelly Roll was performing at Sin City’s Country Saloon in Las Vegas, and Bunnie was with someone else, but sparks immediately flew. And as soon as she was single, the two became an item.

“She was with some abusive douchebag, and they came to a show, and we were backstage,” Jelly Roll told Taste of Country Nights. “They split, and I’m not going to act like I shot my shot. She kind of shot hers. We had mutual friends. She said, ‘Yo. Just plug me in with Jelly.’”

 

4. He was homeless when he and Bunnie started dating.

While he finds it humorous, Jelly Roll’s wife hates when people accuse her of marrying him for money, something that couldn’t be further from the truth.

“I love it when they call her a gold digger, that’s my favorite thing,” Jelly Roll said (via Music Mayhem). “She hates it. It infuriates her, it just flames her up. But it just tickles me pink because when I met her, I was homeless living out of a ’96 conversion van. If anyone was digging for gold, it was I, Popeye. I was the one that was over here searching. I was couch-surfing.”

5. He has his own food truck.

Believe it or not, Jelly Roll actually has his own food truck, which serves donuts and hot wings! The truck, called Rollin’ w/Jelly, travels with him sometimes, and also can be found in and around Nashville. But unlike other businesses, which tend to stay away from those with a criminal past, Jelly Roll will only hire those with a record.

“We only hire second-chance guys,” Jelly Roll told CMT. “Every other place in the world, that’s like, ‘If you’re a felon, you can’t work here.’ We’re only hiring felons. They run the food truck.”

6. He loves Waffle House.

Jelly Roll loves Waffle House. A lot. So much so, in fact, that his dedication to the popular restaurant resulted in an unfortunate lawsuit in 2013, when he released the rap song, “Whiskey, Weed & Waffle House.” After the company issued Jelly Roll a cease-and-desist letter, he vowed to stop eating at his favorite restaurant — a pledge that, fortunately, didn’t last long.

“Even after I vowed I’d never eat at one again, I found myself hungry at an odd hour, under the intoxication of a little whiskey and a little weed, and I wound up in a Waffle House,” he later told FoodBeast.com.

7. He passed his GED on the first try.

Jelly Roll’s life in and out of incarceration meant he spent very little time in the school system. Still, when he decided he wanted better for himself than a life of crime, he took his GED test, surprising himself by passing on his first attempt.

“I spent less than 60 to 70 days in high school,” Jelly Roll told Billboard. “I thought I was a real dumba–. I thought I was learning disabled. I walked in there and smacked [it] out of the park.”

8. There might soon be a slimmed-down version of himself.

Jelly Roll has watched his weight go up and down in recent years, topping in at one time at over 400 pounds. But he is now more determined than ever to be the best version of himself, especially as his career continues to soar.

“I’m going to spend the first couple months of the year just focusing on family and health,” Jelly Roll told Music Mayhem at the end of 2022. “I lost some weight this year in 2022, but in 2023 I wanna finally conquer the demon. I don’t leave for a big tour until about the middle of the year. So I plan on taking the first half of the year to tighten the album up and get some work in.”

9. His musical influences are as diverse as his own music.

Jelly Roll got his start by rapping, but he has always been drawn to country music, along with a wide variety of other genres as well.

“I’m influenced by everything from Three 6 Mafia and UGK to James Taylor, Bob Seger. Some of my favorites … Jim Croce … love the old outlaw stuff,” Jelly Roll told Taste of Country. “I love the old Willie. I love the old Waylon records. Huge fan of all the old Cash stuff. These are probably the guys who really molded my style and sound.”

10. He was heavily influenced by his father, who passed away in 2019.

Jelly Roll’s father, Buddy DeFord, passed away on March 20, 2019, after battling leukemia. Jelly Roll honored his dad with a touching tribute on Instagram on the day that he died.

“Today my best friend of 34 years took his last breath,” Jelly Roll shared. “My father, Buddy DeFord taught me how to wake up, get dressed and go to work. No matter how you feel, you get up get dressed and get your a– to work. He also taught me to hate racism. He would tell me stories about how in the ’60s and ’70s he was the only white guy that would sell meat to the black part of town.

“He taught me all men were created equal in the eyes of God,” he continued. “He taught me how to carry myself as a man, how to shake a man’s hand and look him in the eyes. He taught me how to TREAT people – how to interact with people. How to talk with confidence.”

 

11. He has big plans to help others.

Jelly Roll sold out his 2022 concert at Nashville’s Bridgestone Arena, famously donating all of the proceeds from the concert to build a recording studio inside the Davidson County Juvenile Detention Center, where he was once incarcerated. But his plans for helping those in the same situation he was once in go far beyond one generous donation.

“That’s not even scratching the surface of my plan,” Jelly Roll told the New York Times. “I’m going to build halfway houses and transitional centers — that’s my real heart.”

It’s because Jelly Roll spent so much time in prison that he feels strongly about helping youth who find themselves in the same situation.

“I just never forget being that kid,” Jelly Roll said. “Those years in juvenile were so formative, and it was so devastating for me to miss that time. On my 16th birthday, I didn’t get a car; I woke up incarcerated. I didn’t get my G.E.D. until I was 23 and in jail. I just missed so much of life. So I want to be remembered as a guy that did something for the kids in this town.”