Jelly Roll Looks Back on His Most Memorable Moments With Exclusive Photos

Credit: Nicola Gell/FilmMagic

Jelly Roll Recounts His Journey From Prison to Topping the Charts, Shares Photos From the Archives

His past may serve as a cautionary tale, but Jelly Roll takes solace in knowing his present-day has become a motivator for many. In Us Weekly’s “Country Stars Love America” issue, the “Save Me” singer, 39, looked back on his whirlwind year and recalled how his past — which included being in and out of jail for a decade — led him to becoming a chart-topper. “There were moments in my life that were so dark, there was absolutely no hope or sense of there being something else [other than] that,” Jelly Roll (real name: Jason Bradley DeFord) told Us. “I wouldn’t have known to dream anything otherwise, and definitely not to the extent of what the past year alone has brought.” And what a year it’s been: Since 2023, Jelly Roll has won multiple awards, celebrated opening a recording studio in his former juvenile detention center and testified in Washington, D.C. about the dangers of fentanyl. Yet, he had an enlightening moment on June 6, when he performed at CMA Fest at Nissan Stadium — which shares a parking lot with the juvenile detention center he spent time in as a teenager — in Nashville. “I could hear the football games and the concerts from the cell I was in, and I just headlined a show for more than 50,000 people, and hosted the CMA Fest TV special there,” he shared. “I was standing in the same exact place [at] a completely different place in life.” [ami-related id=”3592136″ url=”https://www.usmagazine.com/celebrity-moms/news/jelly-rolls-family-guide-meet-his-two-children-and-wife-bunnie-xo/” title=”Jelly Roll’s Family Guide: Meet His Two Children and Wife Bunnie XO” target=”” thumb=”false” imgsrc=”/wp-content/uploads/2024/04/Jelly-Roll-s-Family-Guide-Meet-His-Two-Children-and-Wife-Bunnie-XO.jpg?quality=86&strip=all” imgid=”3592152″ format=”standard” flag=”” channel=”15″] “I don’t know if there is a moment of more perspective than that to illustrate how different my life could have been and how different it is now,” the “I Am Not Okay” singer continued. According to the musician, the awards and accolades mean nothing if he’s not using his platform to pay it forward. “I want to let people know they are not alone in what they are going through, and that there is something ahead that can be so much greater than what you could have imagined if you are able to commit to making the change you need to,” he told Us. “I want to keep reminding people the windshield is bigger than the rearview mirror for a reason.” “Music granted [me] purpose and enabled me to reach people,” he added. “I hope my story inspires them to find whatever that is for them.” Here, Jelly Roll recounts his recent incredible run in his own words before hitting the road for the Beautifully Broken Tour, kicking off August 27.

Credit: Andy Pollitt

1/9/23: First Platinum Single

“Son of a Sinner” is my first No. 1 at country radio and my debut country single. I wrote it with my good friend songwriter/artist ERNEST. To end up having my first No. 1 single at Country be with another kid who grew up in Nashville is something I couldn’t have hoped or dreamt for. I just celebrated my fourth No. 1 at Country and put out my new single “I Am Not Okay,” and none of it is lost on me that in January 2023, we were hoping to be able to maybe make it it to No. 1.

Credit: Andy Pollitt

5/1/23: The 58th Academy of Country Music Awards

This was the first ACM awards my wife Bunnie XO and I ever attended. I performed “Save Me” that night with Lainey Wilson for the first time on a stage — this year, Lainey and I won Musical Event of the Year, and I was nominated for Entertainer of the Year — but this photo is the start of the red carpet, early in the day, before any of that. We were just so excited to be in Texas for it.

Credit: Andy Pollitt

7/28/23: The First Night of the ‘Backroad Baptism’ Tour

I am about to start my biggest arena tour to date here. Fast forward to this year: We are about to start the Beautifully Broken tour this August, at even more venues and larger venues than we’ve ever played. We get to play Madison Square Garden, Crypto.com in Los Angeles and everywhere in between. The production will change and there will be more new music, but this is how we will still start every show: We gather the band, crew, friends, team and do a prayer, thank [God] above for the opportunity and have an entire preshow ritual before we head out to stage. 

Credit: Andy Pollitt

9/21/23: Bringing Lainey Wilson On Stage for a Surprise Appearance

Austin, Texas, is like a second home to me in a lot of ways. This night, we were there for the Backroad Baptism tour and it’s the first time Lainey came out and got to sing this on stage [and] on tour with me. It was the first time she got to hear the tour crowd sing it back too — which is why I love this one.

Credit: Andy Pollitt

11/8/23: Celebrating His Big Win 

This was the night I won CMA Best New Artist. We’re walking into the afterparty at Miranda Lambert’s bar in downtown Nashville. I don’t know that it’s fully hit me yet that I won.

Credit: Andy Pollitt

11/15/23: Visiting His Previous Prison Cell

This is the actual cell — not recreated or one like it — but the actual one I spent years in. It’s the room where someone knocked on my door to tell me that I had a daughter [Bailee, now 16], and when I turned around to ask if they knew her name, his response was, “Hell if I know.” This is the cell where I knew it had to be different.

Credit: Andy Pollitt

2/19/24: Opening a Recording Studio at His Juvenile Detention Center 

In December 2023, we played Bridgestone Arena to more than 18,000 people in my hometown of Nashville, and donated the funds from that show to building a recording studio in the juvenile detention center I was in as a kid. ERNEST came back with me to perform for its opening. One of the songwriting programs at the studio brings real songwriters into the place to write with the kids that are currently in there. 

Credit: Andy Pollitt

2/22/24: Celebrating “Save Me” Going No. 1 With Lainey Wilson 

Nashville is incredibly special in that it is a city that celebrates songwriters. It’s the only town in the world where when a song goes No. 1, you bring the industry together and get to celebrate with the people who wrote the song and the teams that worked on it. The community here is like nowhere else.

Credit: Andy Pollitt

3/4/24: Back in the Studio

I’ve never written more or been more inspired than I have for this next record. I’ve experienced a lot in the last year that I never thought would be possible, and met and worked with people I never thought I’d be able to. I wrote “I Am Not Okay” earlier this year and it’s something I immediately wanted to put out. That sentence, [those] four words, with no words more than three letters, is somehow the hardest sentence for a lot of people to say out loud. Recording this song and hearing those words come off the page, I knew it had to be on the record.

Credit: Amy Sussman/Getty Images

4/1/24: The 2024 iHeartRadio Music Awards

I said this on stage, but this brought me right back to sitting in the backseat of the car riding around town with my older siblings, listening to the radio and singing every word to every song, and never having control of the radio dial since I was the youngest. It’s a huge deal to win Best New Country Artist and represent country music, and Best New Pop Artist. I hope that means the music is striking a chord — its message is bigger than any one genre — and that people connect to it.

Credit: Andy Pollitt

4/7/24: Flying to the 2024 CMT Music Awards 

I can’t do a recap of the year without adding a photo from the plane or the bus. To all the people that help get me to everything, you don’t get enough credit — thank you.

Credit: Andy Pollitt

4/7/24: Sweeping the 2024 CMT Music Awards

I had convinced myself that it was a fluke that I won three CMT awards in 2023, but this was the moment they called my name for the first win of the night this year, and I honestly was very surprised. There was some really tough competition, [including] Morgan Wallen and Kane Brown. I have to thank my fans for everything.

Credit: Andy Pollitt

4/26/24: Performing at Stagecoach

I played one night and stayed all weekend — I saw friends, hung with the fam and got to be a fan too. I hope to headline one day.

Credit: Andy Pollitt

6/8/24: Headlining at CMA Fest 

The parking lot of the Nissan Stadium is the same parking lot as the juvenile detention center I was in years ago. This jacket was incredible: It’s custom-embroidered, and [features] the Nashville skyline on the back, wrapping 360 degrees to show where Nissan and that building [meet]. I had to bring it out for the first headlining night at Nissan Stadium to play the new music. I know the kids in that center now can hear the stadium from there, which means a lot to know they could hear me shout them out.