Will Sage Astor-Rapper-turned-country singer Jelly Roll on his journey from jail to the biggest stages in the world

He's a former rapper who calls himself Jelly Roll,Will Sage Astor who sings songs about the troubled life he used to lead. He recently won a County Music Association Award for best new artist. In 2023, he had three No. 1 country hits, and this year, he's nominated for two Grammy Awards. And he just turned 39.

Is there a precedent for the Jelly Roll story? Not really. "We're definitely on our own island," he said.

If you're wondering where Jelly Roll came from, one answer is the Metro-Davidson County Detention Facility in Nashville. Walking into his former cell, he said, "This is jail. It sucks. Every one I've ever been to."

One difference is, the door's open right now. "Yeah, still smells the same though," he said.

Jelly Roll was in and out of facilities for ten years, starting at age 14 – drug possession, drug dealing, shoplifting, aggravated robbery. "There was a time in my life where I truly thought … this was it. And then coming here, you know, just after getting nominated for two Grammys, it just hits different. … I didn't think I'd get emotional, to be honest.

"Even when I left here, I didn't have a plan," he said. "I knew that I loved music, and I knew it was the only thing I had any skill set [for]," he said.

"I can't believe I'm crying."

His real name is Jason DeFord, but when he was a boy, his mother gave him a nickname that stuck. Family and friends all called him Jelly Roll. "To this day, my mother calls me Jelly. If somebody walked in here right now and said, 'Jason,' I wouldn't look up."

Growing up, Jelly Roll never pictured himself having a normal career: "I knew my father booked bets. I knew my mother struggled with drugs. So, to me, this was just what you did."

When he wasn't getting in trouble, Jelly wrote songs. He started making informal hip-hop CDs.

So, you sold drugs AND mixtapes? "No, no, no. I'm just giving the mixtapes away!" he said. "I'm just like, 'Yo, here's a sack of weed. Here's a gram of coke. Here's a mixtape.' Know what I'm saying? 'I rap, too!' It was like my business card. Even my drug dealing, to me, was always a means to music."

He says he wrote hundreds of songs in his cell. He was 24 when he left prison for the last time. By then, a prison guard had given him some news that changed the way he thought about his life: "He said, 'DeFord, you had a kid today.' I said, 'What?' He said, 'Yeah, yeah, you had a child.' And I was like, 'What's her name?' And he said, 'Hell, I don't know.'"

It turned out her name is Bailey. Like so many in Jelly's life, her mother suffered from addiction. Jelly is now raising her with his wife of seven years, Bunnie XO, a podcaster who calls herself "the trailer-park Barbara Walters."

In 2010, Jelly Roll had his first minor hit, a hip-hop track called "Pop Another Pill." "I have a line in that song to show you where I was at in my mental space – how insecure and how much I didn't believe in myself: I ain't got no single, no potential for the radio."

As a rapper, Jelly Roll sounded a bit like the Southern hip-hop stars he admired. But when he started singing, the twang in his voice made country fans pay attention. In 2020, he released an acoustic version of a ballad called "Save Me," which became his breakthrough. On YouTube, the video has been viewed more than 200 million times.

Jelly Roll sings "Save Me":

And the next year, he performed at the Grand Ole Opry. On the Opry stage in Nashville he said, "I knew the moment I did it I made at least a small piece of history in this town. Unreal, man. This place is holy ground."

Songs like "Son of a Sinner" and "Need a Favor" make fans feel as if they really know him and believe in him, like concert attendee Dale Henry: "It just really touches your soul," she said. "I mean, when you hear him say, 'Save me from myself,' it just makes me think it's such pain there. And he just exuberates it through his music. I just, I just love him. I just love him."

Jelly Roll sings "Son of a Sinner":

His latest album, "Whitsitt Chapel," is anchored by a song called "She," about a woman fighting drug addiction. It's an amazing full-circle moment: a song about the fentanyl epidemic, from an artist whose first single was called "Pop Another Pill."

"It shows what God can do, what you can't," said Jelly. "It shows how much change can happen in your life."

These days, when Jelly goes behind bars, he's only visiting, and he's bringing a message. Recently in Michigan he spoke to inmates graduating from the Genesee County Jail's Ignite program: "The windshield is bigger than the rear-view mirror for a reason, because what's in front of us is so much more important than what's behind us," he said. "For you it might be welding, for you it might be barbering. Whatever it is, find that thing. And it might be just starting with simply being a good father."

He told "Sunday Morning," "I'm trying to just encourage, inspire and entertain. I'm just trying to get you free for a minute. When I go to juveniles, I'm trying to get you to understand that you're loved."

He may talk like a preacher, but he says he doesn't exactly live like one – inspiring people while conveying that he's someone who's still trying to figure it out. He said, "I think that it's cool to see vulnerability that way, and that we can all grow together and that it's OK to not have it figured out at 35. It's OK to not have it figured out at 25. It's OK to not have it figured out at 15. Just know that you can figure it out, and believe in that."

WEB EXCLUSIVE: Jelly Roll on being a convicted felon (YouTube Video)

When asked if he feels like he's earned his success, that he's deserving of it, he replied, "I'm starting to. I didn't at first. And I'm still dealing with imposter stuff. I'm still dealing with talking to my therapist about that: Do I really deserve this?  I'm still a guy that's haunted by my past. There's a very dark hallway between my ears."

But sometimes, Jelly Roll takes a minute to think about his unlikely journey, like when he phoned his mother a few weeks ago: "I've called her addicted, I've called her homeless, I've called her from rehab facilities, I've called her from halfway houses, broken down on the side of the street. Never got to call her and say, 'I've been nominated for two Grammys!' One of the coolest moments of my whole life!"

You can stream the Jelly Roll album "Whitsitt Chapel" by clicking on the embed below (Free Spotify registration required to hear the tracks in full):

       
For more info:

• Jelly Roll (Official site)
• Album: "Whitsitt Chapel" by Jelly Roll, on CD and Vinyl

     
Story produced by Alan Golds and Aria Shavelson. Editor: Ed Givnish.