Despite Jelly Roll’s humble beginnings and troubled past, the country music singer, born Jason DeFord in Antioch, Tennessee, is no longer a stranger to the spotlight. After a history with addiction and being incarcerated as many as 40 times, the former hip-hop singer has found success on the country circuit, garnering a total of 4 Grammy nominations, winning the CMA for Best New Artist in 2023, and claiming the big 3 CMA nominations of Entertainer of the Year, Album of the Year, and Male Vocalist of the Year in 2024. At first glance, it might not seem like he has much in common with pop megastar Taylor Swift, but it turns out both singers have strong ties to Hendersonville, Tennessee.

“I take a ridiculous, probably abnormal, amount of pride in being from Nashville, so anytime I can link a Tennessee connect, it tickles me,” he told People in an interview that ran the gamut in topics from career to family time, which is of the utmost importance to the “Sober” singer. “Taylor lived in Hendersonville for a while, and she had bought a playground. I used to push Bailee on that swingset that Taylor donated to Hendersonville.” Jelly Roll boasts an incredibly close relationship with his daughter Bailee, who is now a teenager. They even have the rule that they are to spend no longer than two weeks apart while the singer is working, with Bailee joining him on tour when necessary.

Jelly Roll was eager to share this personal anecdote with Swift the first time he met her, but the encounter didn’t go as planned. “I wanted to tell her that when I met her, but I was so nervous I couldn’t even remember what swingset it was.”

Jelly Roll admits to being star-struck while meeting Taylor Swift

Although he’s a star in his own right, Jelly Roll doesn’t necessarily see it that way. “I might be famous in Antioch, but Eminem’s my friend. I’m not famous,” he told People, referring to the well-known rapper. “The Rock’s my friend,” he continued, mentioning Dwayne Johnson, a popular actor. “I’m not famous. I have famous friends. You know what I mean?”

Perhaps this mentality is what makes it possible for the “Save Me” singer to become star-struck amongst his music industry peers, which is exactly what happened when he met Taylor Swift at the 2024 Grammy Awards. Even though he had every intention of speaking to Swift about taking his daughter to the playground she funded, Jelly Roll recalls being completely tongue-tied when the 14-time Grammy Award winner approached him. “My wife said, ‘I think Taylor’s coming over to holler at you.’ It was like the Red Sea parted for her,” he recalled. The heads-up Jelly Roll got from his wife Bunnie Xo, whom he married in Las Vegas in 2016 after meeting the podcaster at one of his shows, did little to prepare him for a conversation with the “Shake It Off” singer.

“I’m looking at Taylor Swift, and I have a reason to explain to her why I like her so much, and I’m going, ‘You built the swingset somewhere, my daughter, I pushed her on it.’ I did so bad!” he admitted, clearly still not over the encounter. “Definitely was at a loss for words in that moment.” As long as both stars continue on their upward trajectories, it’s likely Jelly Roll will get the opportunity to make a better impression on the Eras Tour headliner in the future.