Inside Jelly Roll’s Intimate Q&A at Billboard Country Live: 9 Biggest Revelations

Jelly Roll got his GED at 24, after spending his 15th, 16th and 17th birthday in jail. He says what finally motivated him to study for it was learning of his newborn baby girl. “It wasn’t a surprise, I knew what was happening, but it didn’t register until that particular moment. … It’s a way more dramatic moment finding out you had a child born when you’re in a concrete slab,” he recalled for the packed crowd. “You’re already contemplating every bad or good thing you’ve ever done. Back then I only knew one emotion: anger. So it made me process that… I went straight down and signed up with the education center that day. [I thought], ‘I have to figure this out for her.’ I found worth in her,” he said through tears.

As Jelly Roll first learned during his Billboard cover story interview, he debuted on the charts back in 2011 when Strictly Business, his collaborative album with rapper Haystack, entered the Top R&B/Hip-Hop Albums chart. “I didn’t know this either, by the way,” he told the crowd before declaring with a laugh, “Find that f—ing distributor!” 

When asked if genre matters — whether he’s known or more successful for his rap or country music — he replied, “It’s just music. This is going to be a hot take; I feel like I always wrote nothing but country songs, just produced weirdly. I just immediately deflected, [but] all my songs were written to tell the truth and tell a story.”

He later called songwriters “the heartbeat of this town,” also adding, “I’m honored to be one of the artists in town who identifies as a songwriter… I’m confident I will do that until I die.”

As he discussed in his cover story, Jelly Roll was unable to leave the country for years due to his criminal record. But recently, he was finally was able to get a passport — and during his conversation revealed he just booked his firs show out of the country. “It’s my first time leaving the country to go do music,” he said, while maintaining just enough ambiguity to keep fans guessing as to when or where that performance will be.

“300 words, that’s the difference between a country song and a rap song,” said Jelly, explaining that the doubled or tripled time code in a rap song allows an artist to fit in more of their thoughts. “I love being able to be as wordy as I want to be… or tell a story with less,” he said. “That’s why [the two genres] marry so well together … Morgan Wallen and Sam Hunt have been so successful from clear hip hop influences,” he added, saying they have more freedom in their storytelling, which helps their music resonates so strongly.

While accepting his Breakthrough Artist of the Year award the night prior, Jelly Roll spoke a good deal about luck and the role it has played in his life and career. When asked to put a percent on the role that luck has played, he replied: “I love your questions… I hate you for ‘em some time… but this is so good” 

After some thought, he came up with the following breakdown: “I’m 55-60% hard work, 15% talent… I had to spend thousands of hours figuring this out, and 25% pure absolute luck. Just perfect timing. I also think I shoveled shit for 30 years and when my heart turned, God was like, ‘I was just waiting on you, big fella.’”

After making some money, Jelly said he tried to do what every rapper does: buy his childhood home. Unfortunately, he said, the current owner “plans on dying there.” He said with a laugh that he was tempted to ask just how old the current owner is, but assured the crowd that if and when the owner does decide to sell, “he won’t sell to anybody else.”

Jelly Roll said he always knew Nashville had his back. “Valets, Uber drivers, Uber Eats drivers, service workers all love Jelly Roll, those are my people,” he said with a smile. “I hope my music helps a guy on a yacht, but it does a whole lot more for a bartender in Antioch. Hits a little different.”

He then admitted the music industry in Nashville though was a less certain sell. He recalled how at first, a handful suggested he go to L.A. and work with someone like Charlie Puth, but he always wanted to make it in Nashville — and with a country artist like Ashley McBryde.

He can now say he sure has, as he and the Grammy winner co-wrote the Whitsitt Chapel hit “Unlive.”

Jelly says he’s protecting his mental health by prioritizing “me time” every night. “I play video games for about an hour every day, it’s my ‘me hour,” he said. “I prioritize a little bit of ‘me time,’ something you love to do, it helps with mental health so much.” He also shared that he makes it a point to call one of his siblings every day, saying how important it is to talk to “somebody who doesn’t give a shit about what Jelly Roll is doing.”

He also spoke on the importance of therapy, and even revealed one of the best tools he’s learned so far. He explained that his wife’s instinct when going through something is to “back away and reassess … but because of my mother’s addictions and struggles, the kid in me wold want to go, ‘What can I do to help?’ The triggers in me would think I did something wrong. I started 30 arguments [with my wife] because I didn’t understand that. I was so selfishly making it about me… It wasn’t malicious, it was a trigger from things I went through that I didn’t even realize.”

“Now things happen in my life and before I react I can catch triggers,” he added. “Identifying them now saves me so much trouble.”

“Now that I learned my dreams were never too small, I’m dreaming properly,” said Jelly Roll with a confident smile. He then shared his hopes for the future, which included playing Nashville’s Nissan Stadium, New York’s Madison Square Garden and Los Angeles’ Crypto.com Arena. He is also gunning for a Grammy, and said he wants the “respect of critics and peers” to come next after sweeping the fan-voted CMT Awards not long ago. “I hope they accept me but if they don’t, fuck it,” he said. “I’ve always got the fans, baby.”

“I never worry about getting an ego because I still struggle with this thing, period,” he added. “No matter how great I am now — and I’m proud of myself for saying that because it took me a long time to feel that way — God’s not done with me. My best days are in front of me.”