Jelly Roll went on The Howard Stern Show on SiriusXM for the first time this week to talk about his life and career, sing his new song “I Am Not Okay,” and perform two covers: Otis Redding’s “(Sittin’ On) The Dock of the Bay” and Hootie and the Blowfish’s “Let Her Cry.”

“I’ve always been enamored by the covers,” Jelly said of Stern’s show on Wednesday. “People come on here and do cool covers. What do y’all think boys, should we just do that?”

Jelly spoke with Stern about his notoriously troubled past and the times he’d been arrested and jailed on drug charges. “I was the worst criminal ever,” Jelly said jokingly when Stern asked about getting caught so many times. “My successfulness of running from the police was zero in 20.”

Aside from the covers, Jelly played two of his own songs: His latest single “I Am Not Okay” and his biggest hit, “Need a Favor.”

Jelly Roll’s had a busy year so far to follow up his breakout 2023. Aside from releasing “I Am Not Okay” earlier this week — his first new music since last year’s Whitsitt Chapel — he performed a live duet with Machine Gun Kelly last weekend at CMA Fest and came out for Eminem’s surprise Detroit performance to perform “Sing for the Moment.”

“When I think about coolest moments of my career, right now at the top, there has to be this thing that I got to go sing with Eminem in Detroit,” he told Entertainment Tonight. “Just what an incredible night, and I got to go do it in Detroit. It was unreal.”