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Jelly Roll Shares Emotional Conversation He Had With Daughter, Who Is Now The Same Age He Was When He Was Arrested (Exclusive)
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Jelly Roll Shares Emotional Conversation He Had With Daughter, Who Is Now The Same Age He Was When He Was Arrested (Exclusive)

The country star tells PEOPLE about raising his 16-year-old daughter Bailee

Christopher Polk/Variety via Getty Bailee and Jelly Roll at the 2024 Kids' Choice Awards

Christopher Polk/Variety via Getty

Bailee and Jelly Roll at the 2024 Kids’ Choice Awards

Jelly Roll was only 14 years old when he was first arrested, but he isn’t afraid his teenage daughter Bailee will make the same mistakes.

In this week’s cover story, the Grammy-nominated singer, 39, opens up to PEOPLE about the conversations he has with daughter Bailee, 16, and recalls a recent conversation in which he reminded her how much potential he sees in her.

“(I said), ‘I don’t judge you by what you do. I judge you based on what I know you are capable of,” he recalls. “You’re so much smarter than I was when I was sixteen. You are so much better, so much more emotionally intelligent. You can read a room so much better. So don’t try to get out of trouble, Miss Sassy, ​​by weaponizing my past.”

Jelly, who is also father to 8-year-old son Noah, says Bailee is “completely ahead” of where he was as a teenager, and he’s confident she has a bright future ahead of her.

Peter Yang Jelly Roll

Related: Jelly Roll Says Some People Are ‘Crazy’ About His Success Because of His ‘Crazy, Narcissistic, Selfish’ Past Behavior (Exclusive)

“When I look at what she does that I hate, I look back at what I did when I was 16, and I think, ‘Oh man…’ If I’m being hard on her about things or a little pushy, you know that it comes from love,” he says.

The “Winning Streak” singer and his wife Bunnie

He and his daughter remain close, and she was by his side earlier this month when he performed at the 2024 CMA Awards. Jelly was behind bars when Bailee was born and has said her birth was a turning point in his life.

“We were very close before it blew up, but she understands what it does for her future and that of the family,” he says. ‘She really is a hammered child. She has been in the same public school district for ten years and has had the same friends since Bunnie and I had custody of her. I think a lot of that helped.”

Amy Sussman/Getty Jelly Roll and Bailee at the 2024 Stagecoach Festival in April.

Amy Sussman/Getty

Jelly Roll and Bailee at the 2024 Stagecoach Festival in April.

Related: Jelly Roll’s Rules for a Sweet Life: Forgiving His Past Self, Prioritizing His Marriage, and Raising a ‘Sassy’ Teen

Bailee recently appeared on Bunnie’s Stupid blonde podcast, and revealed that she hopes to attend Columbia University after high school, with plans to become a criminal defense attorney.

‘I want to go there, and I want to study law. As for music, I don’t have any plans for that right now,” she said.

The teen also revealed that most of her classmates have ignored the fact that she has a famous father.

“We’re all kind of used to it,” she said. “He comes to football games and whatever. So I think everyone’s kind of tired of, ‘Oh, my God.’ And also, people just know not to fuck with me. I’m just not the one. So it’s pretty easy to make new friends, but I just don’t do that anymore.”

For more information about Jelly Roll, pick up the latest issue of PEOPLE, on newsstands everywhere now.