Jelly Roll, an Unlikely New Star, on the Grammys and His Rap Past

Few artists had a more unexpected 2023 than Jelly Roll, the face-tattooed former Southern rapper turned country singer who became one of the year’s most promising new crossover pop stars.

His album “Whitsitt Chapel,” which debuted at No. 3 on the Billboard all-genre chart in June, is a collection of pop-rock anthems with flourishes of country, and it spawned a pair of hits — the introspective “Need a Favor,” and the new version of his viral breakout “Save Me,” featuring Lainey Wilson. He is nominated for two 2024 Grammys at next month’s ceremony: best new artist, and best country group/duo performance.

At 39, with many mixtapes under his belt, Jelly Roll (born Jason DeFord) isn’t a traditional new artist nominee, but his creative rebirth, and move from underground circles to the mainstream spotlight, makes him eligible by Grammy guidelines. His competition includes budding pop, rap, dance, R&B and country acts: Gracie Abrams, Fred again.., Ice Spice, Coco Jones, Noah Kahan, Victoria Monét, the War and Treaty. But Jelly Roll might have the most fascinating back story of them all.

In addition to his radio and streaming success, he has also become something of a pop culture phenomenon. His Hulu documentary, “Jelly Roll: Save Me,” underscores the intense emotional connection that tethers him to his fans, who identify with his hardscrabble struggle tales. (Jelly Roll spent about a decade in and out of juvenile centers and prison beginning when he was 14.) When he won new artist of the year at the C.M.A.s in November, his acceptance speech — part Tony Robbins, part the Rock — went wildly viral. And he got to make an appearance alongside the returning W.W.E. favorite Randy Orton on “Monday Night Raw.”

Jelly Roll recently appeared on the New York Times video show Popcast (Deluxe) to discuss his breakout year, and how he plans to build on it. These are edited excerpts from that conversation.

JON CARAMANICA When you first started making music outside of Nashville in the 2000s, you were a rapper. Who were the people you were looking to for inspiration, coming up during this very rich era in Southern hip-hop?

JELLY ROLL Cash Money Records dominated our mom and pop stores. No Limit. I mean, dude, I remember sitting in a state building where they transition you from one group home to another, shackled, and they have the TV on BET. It might have been the “Bling Bling” video. We were enamored by Southern rap like 8Ball & MJG, Three 6 Mafia, UGK, Outkast, the Dungeon Family, the Geto Boys. Even the earlier side of Swishahouse, Chamillionaire and Paul Wall. Of course, the locals like Haystak. We were just fixing to get our feet wet putting out mixtapes. So we were using every reference we could.

CARAMANICA Were you listening to this stuff for the attitude or the storytelling?

JELLY ROLL The lyrics, the storytelling and the feeling. I think about that whole 8Ball & MJG song [sings “Paid Dues”]: “Trapped in a trap till the mornin’ light/Ghetto ain’t left me no choices, I had to fight/ My mama and daddy was too young to raise me right.”

COSCARELLI You were drawn to the bluesy stuff.

JELLY ROLL I just felt it in my spirit. This is such a dramatic reference point, but it made me feel like when my mother would play “Coward of the County” or she would play Bette Midler’s “The Rose,” and we would all be in there just bawling and crying. I tell people, I think I ended up writing “Save Me” because I’ve been trying to write “The Rose” my whole life.

COSCARELLI Was all of this music the soundtrack to your life as a teenager when getting into trouble with the law?

JELLY ROLL The music always met me where I was. The streets — just to touch on this because I want to be open about it — I thought it was my only choice. I lived in a decently middle-class neighborhood, but I didn’t know one person on my street with a career. Everybody did drugs. People that had jobs were really blue collar. I just was like, I know it’s going to take money to get out of here. And the most obvious way to make money was what was happening in the neighborhood. And it’s no excuse.The music just followed Jason — wherever old Jelly Roll went, he just drug the music along like a Santa sack.

COSCARELLI What did you bring from your rap life into your country music life that’s functioned as a secret weapon for you?

JELLY ROLL That hip-hop hustle. They created DIY: J Prince, Tony Draper, Master P, Birdman. I feel like Southern hip-hop was my saving grace going into country music because I had built a business already. I had built a YouTube channel that had a billion views before I signed a record deal. Just walking into a building and going, Hey, man, I don’t want anybody’s money. What I want out of this building is resources. It was just a different mentality. I had a different negotiating power, and I really understood the importance of ownership.

COSCARELLI You own your recent albums?

JELLY ROLL 100 percent. I own every song I’ve ever released. I do not have a traditional record deal. I still get the lion’s share of my money on every single facet. I didn’t sign a publishing deal. I’m not bragging, but I’m proud of myself because I’m a kid that had zero education and didn’t get his GED till he was 24 in jail.

COSCARELLI During the pandemic, “Save Me” started to go viral and you took a lot of meetings. Did you know you wanted to sign to a country label?

JELLY ROLL I want to release music like a hip-hop artist. I want to write songs like a country music songwriter. And I want to tour like a rock ’n’ roll act. No label in town got it. I want to play the Grand Ole Opry, you know what I mean? And lucky for me, Morgan Wallen was bubbling at the time. He went on to be just the biggest star on earth, which is so deserved. I was like, I can sneak in right now. There’s a moment where I might be understood in this space. And that’s what happened.

COSCARELLI You had these huge hits this year, but you crossed over in another way via your emotional speech at the CMAs, which became a meme.

JELLY ROLL It’s the most viral moment of my whole life.

COSCARELLI And then again on TikTok when you were nominated for the Grammys. How are you so comfortable baring your soul in that way when it’s the first time a lot of people are encountering you?

JELLY ROLL To me, I’m just still me. So whatever’s actually happening in my life is what I’m putting out. I called my mother at the same time. It was me getting to call a woman I’ve called from jail. A woman I’ve called homeless, a woman I’ve called addicted. I got to call her and say I just got nominated for two Grammys. To me, that is the craziest call you can make.

CARAMANICA In your documentary, there’s the really powerful scene with a young woman whose father had been killed. I’m struck by your willingness to be pained by other people, not simply sharing what you went through, but accepting what other people have gone through.

JELLY ROLL Dude, I didn’t cry until I was 34 years old. I can’t quit crying now. I’m an empath for people, period. I genuinely felt that young lady. It’s the only scene I can’t watch in that documentary. I read an article about that scene and cried reading the article. I know what it feels like to be in the darkest moment of your life, man.

To me that goes back to the Grammy post, because it’s like, I’m never going to be too cool to be a fan of something. I think it’s so important to still get excited about stuff.

My wife asked me that day, “What’s this mean to you?” I was like, there is no more pinnacle in the music business than when you win a Grammy. Even just being nominated supersedes every award I’ve already won. That’s the headline the rest of my life — “Grammy nominated.” I’m lying there crying with my wife and we’re looking at all the other nominees. She was like, “You’ve got to post about this.” I was like, too emotional. She’s was like, “When has that stopped you?” And that’s just a good wife.

CARAMANICA So much of this album is emotional bloodletting, but your life is evolving. When you go back for the next album, do you think that there’s a different emotional version of Jelly Roll that’s going to be in the music?

JELLY ROLL I’m never letting what’s happening with the blessing of this thing working for me take me away from who I know I’m actually speaking to. As jovial as I am in real life, the music is a reflection of a very, very dark hallway between my ears. It’s the scariest place on earth for me. I dread going to sleep every night. The ghosts are there. But I’m going into my eighth year of marriage and I’ve never been more in love. I just want a wedding song — I’ve had so many funeral songs. I want to showcase that there are highs in life, too, and I want to figure out a way to incorporate them in the music. But ultimately, you know what I write about, and you know who I write for.