You wouldn’t necessarily picture country superstar-turned-pop megastar Taylor Swift and Jelly Roll as fast friends, but in a new interview, the breakout rapper and country singer reveals his surprising relationship to Swift — and why he was completely tongue-tied when they first met.
Jelly Roll — whose real name is Jason DeFord — used to take his daughter, Bailee, to the park in a Nashville suburb called Hendersonville, which also happens to be where Swift went to high school after her family moved to Nashville so she could pursue her musical dreams.
According to People, Swift donated $100,000 in 2010 to help refurbish the playground equipment at that park, where Jelly Roll later pushed his daughter on the swings.
Jelly Roll and Swift had never met before the 2024 Grammy Awards, when she made her way over to introduce herself.
“My wife said, ‘I think Taylor’s coming over to holler at you.’ It was like the Red Sea parted for her,” the singer tells People. “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! Definitely was at a loss for words in that moment.”
Jelly Roll’s wife, podcast host and influencer Bunnie Xo, caught the moment in a video she posted to TikTok, writing, “When your hubby gets to meet his crush finally.”
Jelly Roll and Swift are both nominated in the upcoming 2025 Grammy Awards, which are set for February.
One thing is for sure when it comes to Jelly Roll: He’ll never miss an opportunity to meet celebs.
As a nominee for his first Grammy in 2024 — he was up for the all-genre Best New Artist — the country newcomer attended the ceremony and hob-knobbed with some pretty big names in the music industry. He met artists like Ed Sheeran, Kelly Clarkson and even Taylor Swift!
Pictures show that Jelly Roll also met Paul McCartney, Sammy Hagar and Lenny Kravitz at the MusiCares Person of the Year ceremony leading up to the Grammys. The show was honoring Jon Bon Jovi, whom he also had the pleasure of meeting.
Here are 20 celebrities Jelly Roll rubbed elbows with during Grammys week.
Jelly Roll is country music’s most fascinating character. His life has taken dozens of wild twists and turns, and he’s been honest about all of it. Here are 25 facts about the “Save Me” singer and his family.
Gallery Credit: Billy Dukes
Jelly Roll’s Teeth Transformation Is Stunning: Before and After
Sterling Whitaker is a Senior Writer and Senior Editor for Taste of Country. He focuses on celebrity real estate, as well as coverage of Yellowstone and related shows like 1883 and 1923. He’s interviewed cast members including Cole Hauser, Kelly Reilly, Sam Elliott and Harrison Ford, and Whitaker is also known for his in-depth interviews with country legends including Don Henley, Rodney Crowell, Trace Adkins, Ronnie Milsap, Ricky Skaggs and more.