Jelly Roll Reveals His Surprising Connection to Taylor Swift — and Why He Was 'So Bad' When He Met Her (Exclusive)

Jelly Roll and Taylor Swift at the 2024 Grammy Awards in February in Los Angeles.Photo:Kevin Mazur/Getty Kevin Mazur/Getty He may be a Grammy-nominated country star, but evenJelly Rollgets starstruck sometimes. Jelly says that upon seeing Swift, 34, he gathered up his courage to tell her about how he used to push hisdaughter Bailee, now 16, on the swings at a children’s playground that she helped fund in Hendersonville, Tenn. “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 explains.

Jelly Roll Says He Wants to Act in a TV Series So He Can Return to the Emmys: 'It's An Honor' (Exclusive)

Jelly Rollalready knows he wants to return to the Emmys! While speaking with PEOPLE andEntertainment Weeklyon the Red Carpet Live show ahead of the 2024Emmy Awardson Sunday, Sept. 15, the musician, 39, said he wants to jump into a television series so he may return in the future after calling his first time at the awards show “the coolest experience.” The country musician and rapper, whose real name is Jason Bradley DeFord, added that he felt “honored” to be asked to perform Sunday’s In Memoriam segment.

Jelly Roll Says Some People Are 'Mad' About His Success Because of His Past 'Crazy, Narcissistic, Selfish' Behavior (Exclusive)

Jelly Roll for PEOPLE.Photo:Peter Yang Peter Yang The country star, 39, opens up to PEOPLE in this week’s issue aboutreconciling with his early days, during which he was in and out of jail some 40 times over 10 years, starting when he was just 14. “I’m rounding third on my amends list, and I think when I get there, I’ll feel a little better,” he says. “I was hitting some stone walls with people that wouldn’t forgive me and I was like, ‘God, maybe this has something to do with the fact [that] I haven’t forgiven myself either.

Jelly Roll Shares Emotional Talk He Had with Daughter, Who's Now the Same Age He Was When He Was Arrested (Exclusive)

Bailee and Jelly Roll at the Kids' Choice Awards 2024.Photo:Christopher Polk/Variety via Getty Christopher Polk/Variety via Getty Jelly Rollwas just 14 years old the first time he was arrested — but he’s not worried that histeenage daughter Baileewill make his same mistakes. Inthis week’s cover story, the Grammy-nominated singer, 39, opens up to PEOPLE about the conversations he has with daughter Bailee, 16, recalling one recent chat where he reminded her just how much potential he sees in her.

Jelly Roll's 2 Kids: All About Daughter Bailee Ann and Son Noah

Jelly Roll’s Kids, Bailee Ann and Noah Buddy.Photo:Jelly Roll Instagram ; Jelly Roll Facebook Jelly Roll Instagram ; Jelly Roll Facebook Jelly Rollis a proud and protective papa bear to two kids: daughter Bailee Ann and son Noah Buddy. The country music singer has repeatedly said how the birth of his daughter in 2008 forever changed his life for the better. On the day Bailee was born, Jelly Roll was in prison for drug dealing.