Jelly Roll’s Rules for a Sweet Life: Forgiving His Past Self, Prioritizing His Marriage and Parenting a ‘Sassy’ Teen

It’s four hours before showtime at Little Caesars Arena in Detroit, and Jelly Roll has The Waterboy playing in his green room. “Bobby Boucher, baby!” he says, referring to Adam Sandler’s character in the 1998 comedy. “One of the greatest movies ever made.”

Jelly is, of course, a Grammy-nominated country singer, worlds away from a football water boy turned celebrated linebacker. But perhaps he sees in Boucher a kindred spirit. They both did, after all, enjoy a redemption arc for the ages, defying the odds to become major stars. And right now, there are few stars bigger than Jelly Roll, the country crooner who’s mined a complicated life riddled with addiction and years behind bars for life-affirming songs that fans say make them feel heard, sometimes for the first time.

“I’m having a ball, man,” the star says. “This started as me just kind of venting and telling my story, until I realized that I was telling the stories of tens of millions of Americans. This is so much bigger than my story.”

If the accolades Jelly, 39, has amassed since pivoting from hip-hop music to country in 2020 are any indication of his reach, he’s right. In the last three months alone, the star — currently on an arena tour across North America — released Beautifully Broken, his first No. 1 album, earned three CMA Awards nominations, including entertainer of the year, ushered in Saturday Night Live’s 50th season as musical guest and notched two Grammy nominations. Then there’s more personal wins, like fatherhood, his thriving marriage to wife Bunnie Xo and his recent 110-lb. weight loss.

A TikTok he posted on Sept. 28 while en route to SNL with a police escort after playing the Global Citizen Festival sums it up: “This is the most insane it’s ever been,” he says, laughing with incredulity. “What the f— is happening in my life right now, y’all?”

Fame Is Entirely Subjective

He may be a cover star now, but Jelly still feels an awful lot like Jason DeFord, who grew up the youngest of four children in Antioch, Tenn. (His mom was the one who gave him the nickname Jelly Roll.) As a kid, he soaked in his siblings’ and his parents’ musical tastes, which ran the gamut from rap and Metallica to Waylon Jennings, Kenny G and Jim Croce. “The greatest thing that happened to me was being the youngest child because I never controlled the radio,” he says. “I became a little jukebox.”

Though he began his career as a hip-hop artist, putting out a number of independent mixtapes and albums, the 2020 release of his song “Save Me” saw him pivot to country music, and introduced the world to a new, unguarded Jelly — one desperately seeking salvation for his sins. His soulful lyrics — which tell the story of his troubled past, during which he was in and out of jail some 40 times before turning his life around — resonated with his new audience, and before long, he’d become the genre’s biggest rising star.

Fame has certainly changed his life. But he views the spotlight differently than others in his position might. “I might be famous in Antioch, but Eminem’s my friend. I’m not famous,’ he says of the iconic rapper, with whom he collaborated on the song “Somebody Save Me.” “The Rock’s my friend. I’m not famous. I have famous friends. You know what I mean?”

Ascending to the spotlight so quickly has been a complicated journey for Jelly, who says his emotions often vacillate between feeling “awkwardly uncomfortable or a little over comfortable” in the spotlight.

“I still feel like that kid from Antioch more often than I don’t,” he says.

But the reminders that he’s grown into something more continue to pop up. He says the 2024 CMA Awards, at which he’s nominated in the big three categories (male vocalist, album of the year and entertainer of the year) is a “huge” moment.

“Dude, you don’t get no bigger,” he says. “We went from only being qualified to walk the carpet, didn’t even have a seat for us in the building, to winning new artist of the year. And then to being nominated for the big three. I’m in a category with people that I was watching win CMAs on TV when I was incarcerated. That’s crazy.”

Music Has Real Healing Powers

Jelly’s first country record, Whitsitt Chapel, was released in 2023. At that point in his career, he’d already released some 300 songs. But that album, which signaled yet another reinvention for the man who’s all but become the face of positive transformation, was his most personal up to that point, and he spent about three months writing it.

When it came to putting out Beautifully Broken — which contains hits like “Winning Streak” and “I Am Not Okay” — in October, he had some more breathing room. This time, he wrote his record over the course of 15 months.

“Every album is a labor of love, and the day they’re not, I’ll quit. It’s that easy,” he says. “Admittedly, there are things that I do in my career that feel like work, and I don’t like that word. That’s why I got in the music business! But going to write a song has never been one of those things. Never one time have I looked at my calendar and seen ‘Songwriting session’ and been like, ‘F—, I’ve got so much other s— to do today.’ Normally I’m like, ‘Oh yes, I can exorcize some of these demons.’”

With most of those demons now in his rearview, Jelly is as close to finding peace as he’s ever been.

“I’m rounding third on my amends list, and I think when I get there, I’ll feel a little better. I was hitting some stone walls with people that wouldn’t forgive me, and I was like, ‘God, maybe this has something to do with the fact [that] I haven’t forgiven myself either,” he says. “I brush over 10, 12, 15 years of living an extremely crazy, narcissistic, selfish lifestyle in a two-second sentence in an interview. The truth is, there was a lot of pain in there. I hurt a lot of people. No matter much I’ve changed, they still watch and are mad that I’m successful. I understand that. But I’m doing better at letting go of the past and realizing that I don’t owe that part of me anything.”

Jelly has never been one to place all his eggs in one basket. In fact, the star likens his attempts at breaking into the music industry to a baseball player: he would rather have been the worst major league player to ever take the field than be the best AAA player that ever lived. 

But now that he has found success, he’s unlocked a new fear: losing what he’s built.

“I was never afraid of not making it. I’m petrified of losing it,” he says. “That is the pressure I feel. I was okay with this thing not working. But since it worked, now I’m petrified of it not working.”

Family Is an Anchor

“My world shrunk when I focused on one woman,” Jelly says, proudly referring to his wife, the podcaster Bunnie Xo, 44. After meeting at one of Jelly’s shows in 2015, the couple eloped in Las Vegas in 2016, with Bunnie taking on the new role of stepmom with ease (Jelly is dad to daughter Bailee, 16, and son Noah, 8, from previous relationships).

Jelly credits his close-knit family with helping him focus on a brighter future, and they remain pillars of support as stardom continues to rock his world. “I prioritize family, and that’s what anchors me down,” he says. “Everything that I believe going right for me is in the fact that I’m pretty grounded in my family.”

Bunnie and Jelly never spend more than two weeks apart, and the couple recently implemented the same rule with Bailee, who now joins her dad on tour every other weekend. Bunnie previously explained the family dynamic on an episode of her Dumb Blonde podcast, saying they’ve had full custody of Bailee since 2017 due to the Bailee’s mom’s struggle with drug addiction (Jelly has since said that Bailee and her mom are working on mending their relationship).

Though Jelly says his daughter doesn’t love the ways in which his recent fame has “taken away from the us time,” she recognizes the good it’s doing their family.

“We were really, really close before it exploded, but she understands what it’s doing for her future and the family’s future,” he says. “She’s a really hammered down kid. She’s been in the same public school district for 10 years and had the same friends since me and Bunnie have had custody of her. I think a lot of that has helped.”

Kids Will Make Their Own Mistakes – And You Have to Let Them

Jelly is well aware that Bailee is the same age now as he was when he made the decisions that would nearly derail his life. The singer was first arrested at age 14, and spent the next 10 years in and out of prison on charges ranging from aggravated robbery to possession with intent to sell cocaine.

Bailee’s birth — which came while Jelly was behind bars — marked a turning point in his life, inspiring him to clean up his act. Nearly two decades later, he’s done that, kicking a hard drug addiction on his own and sticking to alcohol and marijuana in moderation, while embracing the role of family man.

“She’s special. She’s different. She’s totally ahead,” he says of his teenage daughter (son Noah stays largely out of the spotlight). “When I look at what she does that I consider horrible, I look back at what I was doing at 16, and I’m like, ‘Oh man…’ When I’m hard on her about stuff or a little pushy, she knows it’s from love.”

He understands that Bailee will make her own mistakes — and is wiling to let her. He recaps a recent conversation between the two: “I don’t judge you based on what you do. I judge you based on what I know you’re capable of. You’re so much smarter than I was at 16. You’re so much better, so much more emotionally intelligent. You can read a room so much better. So don’t try to talk your way out of getting in trouble, Miss Sassy, by weaponizing my past.”

Even Stars Get Starstruck Sometimes

He may be a celebrity himself, but the Taylor Swift effect remains strong. Jelly recalls meeting Swift for the first time at the 2024 Grammy Awards, and gathering up his courage to tell her about how he used to push Bailee on the swings at a children’s playground she funded in Hendersonville, Tenn.

“I take a ridiculous, probably abnormal, amount of pride in being from Nashville, so anytime I can link a Tennessee connect, it tickles me,” he explains. “Taylor lived in Hendersonville for a while, and she had bought a playground. I used to push Bailee on that swingset that Taylor donated to Hendersonville. I wanted to tell her that when I met her, but I was so nervous I couldn’t even remember what swingset it was.”

Jelly says coming face to face with Swift was the very first time he’d ever choked on his own words, despite the fact that she’d been the one to approach him.

“My wife said, ‘I think Taylor’s coming over to holler at you.’ It was like the Red Sea parted for her,” he says. “I’m looking at Taylor Swift and I have a reason to explain to her why I like her so much, and I’m going, ‘You built the swingset somewhere, my daughter, I pushed her on it.’ I did so bad! Definitely was at a loss for words in that moment.”

Jelly has linked up with some of music’s biggest stars, including Eminem and Lainey Wilson. But he has his eyes on collaborating with other stars, too, like Miley Cyrus, thanks to the Tennessee connection, and The Weeknd, whom he considers “the greatest artist of this generation.”

If Your Music Reaches Just One Person, It’s Worth It

Jelly admits it can at times be “overwhelming, in a good way” when he hears the stories of people his music has touched. Whether it’s fans telling them his song played at their child’s funeral, or someone saying his music inspired them to get sober, his reach has extended beyond his wildest dreams.

“When I wrote [‘Past Yesterday’] … all we talked about the whole time was, like, if just one person hears this song and it feels like it’s telling a story they’ve never told or couldn’t tell themselves, this song is worth it,” he says of the track, about a child experiencing sexual abuse. “If that’s how I feel about one line from one song and one person being touched by it, you can imagine how overwhelming it is to get thousands of messages a month of people saying similar things about different songs.”

Jelly says he stopped thinking of himself as an entertainer when he released Whitsitt Chapel, and was instead overcome with the realization that his goal is to be “as impactful as possible” through his music.

“I realized we’re here to serve,” he says. “That’s the thought when I write, when I perform, when we go feed the homeless, when we go talk to kids at juvenile [detention centers] or jail — we just want to be a good steward with what we’ve got.”

He says philanthropy is the legacy he hopes to leave behind and notes he recently raised more than $1 million from pre-orders of his latest album, which he donated to four different charities.

Then there’s the smaller but just as impactful moments in which he pays it forward to the people and places that raised him. During a visit to his old high school in Antioch, his first since he’d been expelled from the school, he was approached by a teenager decked out in clothes he’d made himself.

“I was like, ‘Yo, make me a pair of pants. I’m going to wear them for something big,’” Jelly recalls. “So he went and listened to some interviews and saw who some of my favorite artists were and some of my stories and made me this pair of pants.”

True to his word, Jelly did save the pants — which feature headshots of artists that inspire him, like Jim Croce and James Taylor — for a special occasion: his PEOPLE cover shoot.

“He’s just such an inspiration. I don’t think there’s a more deserving superstar,” says Ernest, the mononymous country artist who co-wrote “Son of a Sinner” with Jelly and has opened for him on the road. “He truly believes in giving back.”

Though Jelly jokes that it’ll take a few more albums for him to write a “completely hopeful” record, he’s more optimistic now and happy to let things… well, roll. 

“An old dude in jail once told me, ‘If you want to find a pearl, you’ve got to shuck a bunch of oysters,’” he says. “So if the world’s my oyster, I’m going to keep shucking and finding pearls, baby.”