Jelly Roll Brings A Grammy‑Sized Dose Of Hope To Nashville's Prison Walls

Jelly Roll's award-winning starship qualities extend beyond the microphone and studios.

The Grammy winner revealed his plans for his recently won awards, and they include touching on a part of his past to ignite hope. The Nashville native would be donating one of his monumental achievements to the county jail to serve as a source of inspiration to the inmates.

Jelly Roll went home on Sunday night with three huge wins. He won the Best Contemporary Country Album category,  Best Country Duo/Group Performance,and Best Contemporary Christian Music Performance/Song.

Jelly Roll walked off the 2026 Grammys with three wins for the shelf, but all three awards would not be sitting on the shelf, the artist shared. His wife, Bunnie Xo, already shared at the end of the night that she would be keeping one for herself because she feels she deserves it, while Jelly Roll later divulged his plans for the remaining two.

The singer told Entertainment Tonight in an exclusive interview, as he sat down with fellow "Star Search" judges Chrissy Teigen, Anthony Anderson, and Sarah Michelle Gellar, who congratulated him on his win, that he would be holding on to one and giving one away.

"I'm going to obviously keep one at the studio because that was my dream, amd I think I'm going to give the second one to the county sheriff, Daron Hall, to put at the jail," the country singer said amid smiles.

Immediately, Gellar added, "So people know there's a life after," while Jelly Roll affirmed that his wife would have the other one. The rapper won twice in the pre-show event, one for Best Country Duo/Group Performance with his Shaboozey collaboration, "Amen."

For Best Contemporary Christian Music Performance/Song,  he shared with "Hard Fought Hallelujah" collaborator Brandon Lake. He closed the night with a big win for Best Contemporary Country Album for his 2024 LP, "Beautifully Broken."

The father of two has been an open book about his past and criminal history, sharing that he was once a troubled youth.

In his 2023 documentary, "Jelly Roll: Save Me," the artist shared that he had been to jail around 40 times for a range of different offenses, including possession with intent to distribute and aggravated robbery.

He spent ample time in Tennessee prison as a convicted felon before kickstarting his career as a musician. His behavior went on for years until he became a father in 2008. Jelly Roll welcomed his first child, Bailee, whom he gained full custody of in 2016.

Her birth while he was incarcerated marked the turning point of his life, and his son, Noah, was born in August 2016. US Magazine shared that Tennessee Governor Bill Lee pardoned Jelly Roll in December 2025 of his past convictions, saying that the singer had an outstanding life story. 

"His story is remarkable, and it's a redemptive, powerful story, which is what you look for and what you hope for," the Governor said.

Walking up the stage to receive his third award for the evening in the category that included entries from Miranda Lambert, Tyler Childers, Eric Church, and Kelsea Ballerini, the "Save Me" singer smiled amid cheers.

He then delivered a moving speech where he expressed gratitude to the love of his life for her support. He opened his speech with "First of all, Jesus, I hear you and I am listening, lord."

Jelly Roll shared that if Jesus and Bunnie Xo had not been by his side, he would have wound up dead or in jail once again. The artist dug deep into a dark part of his life, detailing when he was struggling with many vices, adding that God and music changed his life, Forbes shared.

Explaining further, Jelly Roll recalled a time in his life when all he had was a bible and a radio while he was in jail before declaring his faith in Jesus and telling the audience that they could all have a relationship with JESUS.

The rappers win marks a first for the Best Contemporary Country Album. The category was previously called Best Country album, but the Recording Academy split it this year, also introducing the Best Traditional Country Album category withthe hopes to better define country music.

Unlike other artists who delved into the political conversations, especially surrounding the U.S. Immigration and Customs Enforcement, Jelly Roll maintained that he would remain silent on the matter.

He told reporters backstage that he does not intend to comment on what is going on in the country currently. He explained that he does not believe his opinions on the matter are relevant, saying that while he appreciates that people are interested in what he has to say, they should not be.

The artist added that his feelings about politics stemmed from his upbringing, stating that political matters were not a topic of discussion while he was growing up.

The Blast shared that the country singer described himself as disconnected for ongoing events, referencing the 18 months he went without a phone. He added that his silence was not permanent as he has plans to make a statement in the near future.

Jelly Roll and his wife are ready to grow their family. While the singer has two children from previous relationships, the power couple is looking into modern medicine to help them achieve their dreams.

The father of two, while commenting on an 8-year-old aerialist, Kaylen Fairchild's performance on "Star Search," said that watching her tripled his baby fever.

The podcaster has also previously opened up about their desire to have a child together. As shared by The Blast, they had decided to give IVF a try and have recently had a "huge win."

Although Bunnie Xo clarified that she is not pregnant yet, despite their attempts, the pair has decided to trust God with the process, and they are open to adoption.

While waiting, Jelly Roll has doubled down on his role as a father to Bailee and Noah, sharing that he strives daily to be a better parent and build fun memories with his kids.