While incarcerated, Jelly Roll found his passion for music and began writing songs in his cell. Stern found it fascinating that Jelly could find a beat for the lyrics he was writing.

“You just kind of start humming melodies over this loop, over this kind of track in your head. You go from there. The hard part is when you are writing so many of them, Howard, you start forgetting them.”

Jelly Roll then says that the most challenging part of writing music while locked in was the inability to record the melody that he perfectly crafted to the lyrics. While he could write down all his lyrics on paper, Jelly Roll said that he had lost so many great melodies because there was no way to record them:

“So what ends up happening is, and this worked out for me a lot, is that I would come home with a bunch of songs that I couldn’t remember the melodies to, but I had really good lyrics….at least pen out the lyrics and keep the lyrics as tight as possible.”

After Jelly Roll details how he started his writing career while locked up, Stern inquired about how Jelly Roll decided he was going to bet it all and try out music once he was released from prison.

While Stern and Jelly were both giggling at how crazy of an idea it probably sounded coming out of his mouth that he was “going to be famous one day,’ Jelly Roll did stick to his guns and made it happen but agreed that he probably looked like a grade-A looney telling all of his cell block friends he was going to make a living out of music:

“Especially when I was leaving jail for the last time this a stack of songs like this (holds up a textbook-size stack) because I wrote them all on paper. I had a whole bag of songs, I had my little knapsack of songs and walked to people’s cells going, “If I ever see you again, I’ll be at Madison Square Garden.”

Jelly Roll’s friends were not the only ones skeptical of him making it… even his family was: