Jelly Roll Explains Why Prison Was Easier for Him Than Stardom

Jelly Roll is one of the biggest breakout stars in country music over the past two years, after spending much of his youth and early adulthood in jail and prison. But in a surprising new interview, the "Halfway to Hell" singer admits that in some ways, he found prison easier to deal with than his newfound celebrity status.

Jelly Roll appeared on The Howard Stern Show on SiriusXM on Wednesday (June 12). The rapper-turned-country superstar spent years of his early life behind bars as a result of his involvement in drugs and drug dealing, and he agreed with Stern when the host pointed out that for someone who faces long-term incarceration, "in some ways, prison or jail or juvey or whatever becomes more of a home than your home."

"Yeah, it's safe. There's a sense of safety there," Jelly Roll admits. "When you were in the streets, there was no safety. Anything could happen at any time. It's a constant wild card. It's anything goes."

"Rule No. 1 of the streets is there are no rules. Rule No. 2 is, don't forget No. 1," he adds.

"Which world is easier to navigate for you — the world of prison, or the world of celebrity?" Stern asks.

"Prison," Jelly Roll answers without hesitation. "So much easier."

"So much easier because you know how to function in a jail, you know what to do," Stern observes. "But now when you're backstage and someone says Paul McCartney wants to meet you, that's new territory."

"That's new territory," Jelly Roll agrees. "You p--s yourself a little bit," he adds with a laugh. "Just a small dribble."

Elsewhere in the interview, Jelly Roll told the hilarious story of how he tried to outrun the police at age 15 while he was high on Xanax -- which didn't quite turn out the way he envisioned.

"I was the worst criminal ever," he admits with a laugh. “My successfulness of running from the police was zero in 20.”

Jelly Roll just scored his fourth No. 1 hit in a row on Billboard's Country Airplay Chart with "Halfway to Hell. His upcoming 2024 Beautifully Broken Tour is one of the most-anticipated country tours of the Summer of 2024.

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.

Jelly Roll: 23 Stunning Facts About the 'Save Me' Singer

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 23 facts about the "Save Me" singer and his family.

Gallery Credit: Billy Dukes

11 Songs that Foreshadowed Jelly Roll's Country Music Career

Jelly Roll has taken the country music world by storm over the past year, and he will release his first full-length country album, Whitsitt Chapel, on June 2. Before he jumps right into the deepend of the genre, let's take a walk down memory lane. There are 11 songs that seemed to foreshadow his country music career.

20 Totally Adorable Pictures of Jelly Roll and His Wife, Bunnie Xo

Jelly Roll and his wife, Bunnie Xo, never shy away from public displays of affection. The pair have shared numerous photos together sneaking kisses or engaged in deep belly laughs. Jelly Roll and Bunnie Xo married in 2016 and are closer than ever today.

20 Songs Jelly Roll Plays The Most During His Shows

Jelly Roll has been a touring machine in recent years. He is following up a busy 2023 with a another huge tour in 2024.

We recently went through all of the setlists from his shows using Setlist.fm to determine the songs you'll mostly likely hear if you get tickets to a Jelly Roll show. Here is a look at his most played songs.

(NOTE: Song stats are through March 26, 2024)

Gallery Credit: Rob Carroll