If you saw a guy with a face full of tattoos crying on a Nashville stage in late 2023, you weren't alone. Millions of people watched Jason DeFord—known to the world as Jelly Roll—basically break the internet during his first big night at the CMA Awards. It wasn't just about the music. It was about the fact that a 39-year-old former inmate was standing where "polished" stars usually live.
Honestly, the Jelly Roll CMA Awards journey is the kind of stuff scriptwriters wish they could invent. He didn't just show up; he kicked the door down.
The Night Everything Changed: 2023 CMA Awards
Most "New Artist of the Year" winners are in their early twenties, fresh out of a college dorm or a TikTok viral moment. Jelly Roll was 38 going on 39. He had spent a decade in and out of the justice system before ever touching a country music chart.
When he won New Artist of the Year at the 57th Annual CMA Awards, the room felt different. You could tell the "industry" was finally catching up to what the fans already knew. He beat out some heavy hitters like Zach Bryan and Megan Moroney.
His speech? Legendary.
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He didn't do the standard "thanks to my agent" rehearsed bit. Instead, he screamed at the back of the room. He told anyone going through a hard time to keep going. He famously said, "The windshield is bigger than the rearview mirror for a reason because what's in front of you is so much more important than what's behind you."
It went viral instantly. People who didn't even like country music were sharing the clip.
Wait, Did He Actually Break the Award?
Yeah, he did.
In the chaos of the press room and the excitement of the night, Jelly Roll actually dropped and broke his CMA trophy. Most artists would have been devastated, but he just laughed it off. It kinda fits his brand, right? Nothing in his life has been "perfect" or "pristine," so why should the trophy stay in one piece? He eventually got it fixed, but that moment of human clumsiness made him even more relatable to the average person sitting on their couch.
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2024 and 2025: From Newbie to Headliner
Fast forward a bit. By the time the 2024 CMA Awards rolled around, Jelly Roll wasn't the underdog anymore. He was the main event.
He opened the 2024 show with a performance of "Liar" that featured Keith Urban on guitar. It was a massive moment of validation. Think about that for a second: a guy who used to sell mixtapes out of a car trunk was now being backed by a literal guitar god and CMA veteran.
Key Moments from Recent CMA Cycles:
- The Power of "Save Me": His collaboration with Lainey Wilson became the emotional backbone of the awards circuit. They performed it together, and it felt like a religious experience for the audience.
- The 2025 Shift: By early 2025, Jelly Roll started sweeping categories he wasn't even considered for a few years ago. We’re talking Musical Event of the Year and massive nominations for Male Vocalist of the Year.
- Cross-Genre Domination: He’s one of the few artists who can perform at the CMAs on Wednesday and be discussed in hip-hop or rock circles by Thursday.
Why the CMAs Love Him (and Why Some Critics Don't)
There’s always a bit of drama, isn't there?
Some "traditionalists" think Jelly Roll isn't "country enough." They point to his hip-hop roots and his unconventional look. But here’s the thing: country music has always been about "three chords and the truth." Jelly Roll has the "truth" part down better than almost anyone.
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The Country Music Association (CMA) recognized that he was bringing a whole new audience to the genre. He speaks to the "forgotten" people—the ones who have struggled with addiction, the ones who have been to jail, and the ones who feel like they don't fit in. That's a massive demographic that country music hadn't fully tapped into in years.
The Business of Jelly Roll at the CMAs
Success at the CMAs isn't just about the trophy. It’s about the "CMA Bump."
After his 2023 win, his album Whitsitt Chapel saw a massive spike in streams. By the 2024 and 2025 seasons, he was headlining stadiums. The industry calls it "validation," but for Jelly, it was "survival." He has used the CMA platform to lobby for change, even testifying before Congress about the fentanyl crisis. He uses the spotlight the awards give him to talk about things that actually matter.
How to Follow His Journey Moving Forward
If you're looking to keep up with his award season runs, here’s what you should do:
- Watch the Replays: Go back and watch his 2023 acceptance speech. It’s a masterclass in raw emotion.
- Check the 2026 Projections: He’s already being eyed for major categories for the upcoming cycle, including Entertainer of the Year.
- Listen to the Collaborations: His CMA performances are usually better than the studio versions because of the raw energy. Look for the Keith Urban or Brooks & Dunn live cuts.
Jelly Roll didn't just win a CMA award; he changed what a "country star" looks like. He proved that it’s never too late to start over. Success isn't about having a clean record; it’s about what you do with the time you have left.
Next Steps for Fans: If you want to dive deeper into his actual music beyond the awards, start with the Beautifully Broken album. It captures the exact energy he brings to the CMA stage—messy, honest, and completely real. You can also track his latest nominations on the official CMA website as the 2026 season approaches.