Jelly Roll Shares ‘Beautifully Broken’ Story In Pollstar Live! Keynote With Michael Rapino

A crowd of Pollstar Live! attendees packed the International Ballroom at the Beverly Hilton April 17 to hear the remarkable story of the years-in-the-making overnight success of unlikely country megastar Jelly Roll, fresh off his Pollstar Awards win for Country Tour of the Year the night before.

Jelly Roll — his real name is Jason DeFord — sat with Live Nation president and CEO Michael Rapino for a freewheeling discussion of his life, career and, briefly, what he’s learned about animal behavior.

Rapino took a pause from his prepared questions to ask Jelly about his donkeys which have been featured in several viral social media videos.

After buying the first donkey, Jelly felt like the animal was depressed and assumed, due to what he’d learned from “Winnie the Pooh” and the perpetually sullen Eeyore, that donkeys were just naturally sad. But the first donkey perked up considerably after getting a buddy.

“Eeyore just needed another donkey,” Jelly said.

Jelly pivoted then to talk about his social media strategy more broadly, which is managed largely by his wife Bunny, because he himself doesn’t “even have a phone.”

“We took a no fourth wall approach from the go. From day one, we said we should do all access all the time,” he said. “She films all day. I don’t know what she puts out. … We lived in shame for so long, we wanted to get out of that.”

His climb to stardom has been well-documented, including in the pages of Pollstar. He said he spent “90 percent” of his teens and twenties being incarcerated in either juvenile detention facilities or jails and prisons. Until nearly 17 years ago when he found out — while behind bars — he’d become a father. He calls it his “road to Damascus” moment, one of many references he makes to his faith..

“I came home and started hustling,” he said. “Selling t-shirts and mixtapes out of my car.”

He eventually linked up with Nashville-based CAA agent Hunter Williams and on the verge of a label deal, decided to start looking for a manager.

“I was talking to labels in LA and I said to myself I should find a Nashville manager, but when I talked to Nashville labels, I said I should talk to a New York manager,” he said.

His reasoning was that he’d seen the politics of Music Row and reckoned a Nashville manager who had other country clients would have to “play politics” on behalf of and sometimes between his own clients.

“So I literally prayed for an old New York guy and specifically a hip-hop guy,” he said.

Two days later, his business manager said he’d arranged a call with WITH Management founder and long-time hip-hop manager John Meneilly.

“I was fixing to sign what I then didn’t know was a huge deal. I thought I was rich already,” he said. “John said let’s reassess this and before that I had negotiated all my own deals.”

And then, staring down his forties, Jelly’s career took off. In 2023, he was the CMA winner for Best New Artist, the second-oldest winner of that award. He was nominated for a Best New Artist Grammy, the second-oldest nominee for that award in history.

And now, he’s getting ready for the rest of his career and his life. He’s lost more than 150 pounds and is preparing to run his second 5K. And this time, he won’t stop for a joint as he did in his first.

“I come from the opposite of something,” he said. “I want to be coming to arenas for a long time and I have to be a better version of myself to do that.”

This summer, he’ll tour stadiums with Post Malone and after that, he wants to do a major tour of his own which includes multiples on most stops. He finally played a plus-one in Edmonton on his first run through Canada and it was so new to him his crew had to explain to him what a “walkaway” is.

On that next big tour, he’ll continue to donate to local charities and visit incarcerated people, as he’s done throughout his rise to stardom.

“I grew up in a place where a lot of people didn’t show up for us. When you get in a situation to show up for people, you want to show up, he said. “If you need a blessing be a blessing.”