Jelly Roll is revisiting his colorful history. The 39-year-old "I Am Not Okay" singer was a guest on Wednesday's episode of SiriusXM's The Howard Stern Show, where he opened up about the realities of his criminal past and incarceration.
"There's a sense of safety in there," he said of jail. "When you were in the streets, there's no safety. Anything could happen at any time."
He added, "At least in jail was this little bit of comfort and chance to regroup and you'd always sell yourself the dream in jail, too. 'Oh, I'm gonna figure this out. I'm changing. I got an idea.'"
Jelly Roll visits SiriusXM Studios on June 12, 2024 in New York City.
The country star -- whose real name is Jason Bradley DeFord -- has previously said that he's been to jail some 40 times over the years. He was notably arrested at 16 for aggravated robbery and at 23 for drug dealing.
"I was the worst criminal ever," Jelly told Howard Stern. "My successfulness of running from the police was zero in 20."
The two-time GRAMMY nominee recalled one such failed instance when he was just 15 years old.
"When the police pulled us over, I was like, 'I'm just gonna run,'" he shared.
"In my mind, I jumped out [of the car] and sprinted across the field and almost made it,” he continued. "I was so fat and Xanax-ed out, I stood out and got two steps. The cop was standing there, watching me, and I fell, and he just laid on top of me."
He added with a laugh, "He felt so bad for me that he didn’t even charge me for trying to run."
Jelly Roll performs at Live from Detroit: The Concert at Michigan Central on June 6, 2024 in Detroit, Michigan
It was during one of his incarcerations that Jelly became a father, and his now 16-year-old daughter Bailee was born.
"I honestly think if I wouldn't have had a kid, I would’ve never broke that cycle," he told Howard Stern.
Today, Jelly has full custody of Bailee and is raising her alongside his wife, Bunnie XO, whom he married in 2016. That's the same year that he welcomed his second child, son Noah, with a former girlfriend.
Jelly and Bunnie, 44, recently revealed that they are undergoing IVF in hopes of growing their family.
"My wife and I are talking about having a baby. And it really made me realize, at almost 40, I was like, 'That means I gotta live till at least 60. I gotta see this kid into college,'" he said on the Bussin' With the Boys podcast.
Bunnie reposted the podcast clip on Instagram with writing on top, explaining their decision.
"We had planned on doing this privately, but decided our IVF journey needed to be shared because we've always been so open. And w/ all odds stacked against us, it's already been hard & we have only just begun," she wrote. "J & I are so excited & scared all at the same time."
"We genuinely never thought we'd want to add to our family but something changed this year & we both just want a piece of us together to add to our already perfect family with Bailee & Noah," Bunnie added.
The couple first met at one of his shows in 2015 and quickly sparked a romance. The pair got engaged in 2016 and decided to tie the knot the same day at a chapel in Las Vegas. He has since credited her as "a beacon of change in my life," per a 2023 interview with Billboard.
Bunnie XO, Jelly Roll and Bailee Ann DeFord.
In his interview with Stern, Jelly admitted that his biggest fears today stem from his role as a parent.
"My fear now is [for] the people that I love," he said. "It's the new fear I never thought I'd have, like, the way we feel about our children."
RELATED CONTENT:
