Jelly Roll (real name Jason DeFord) was in prison mainly because of drug- related charges and an aggravated robbery he committed as a teenager.

Quick Scoop: Why Was Jelly Roll in Prison?

  • He first got in trouble with the law around age 14, mostly for drug possession, dealing, and related offenses.
  • At 16, he was involved in an aggravated robbery that included a gun and was over weed , which he’s called the worst decision of his life.
  • That robbery led to a felony conviction and an eight‑year sentence , though he served just over a year in custody plus years of probation.
  • In his early 20s, he was locked up again for dealing drugs , and he was actually in prison when he found out he’d become a father, which he says jolted him into changing his life.
  • Overall, he has said he was arrested around 40 times and spent nearly a decade cycling in and out of juvenile detention, jail, and prison before turning his focus fully to music.

“This is a grown man looking back at a 16‑year‑old kid that made the worst decision that he could have made in life and people could have got hurt and, by the grace of God, thankfully, nobody did.”

What Exactly Were the Charges?

  • Aggravated robbery (with a gun, over marijuana) at 16, charged as an adult.
  • Multiple drug charges , including possession and dealing, especially around his early 20s.
  • Other earlier offenses reportedly included shoplifting and similar low‑level crimes tied to that lifestyle.

Because of Tennessee’s strict rules on violent felonies, that aggravated robbery has followed him for life, affecting his ability to vote, own a firearm, get a passport, and travel or work overseas.

From Prison to Spotlight (Trending Context)

In recent years he’s become a Grammy‑nominated country star and a prominent example of someone who turned a heavy criminal past into a redemption story. He often talks about his incarceration in interviews, documentaries, and on podcasts, framing it as a warning about bad choices and a motivation for his music and advocacy work, including speaking out on addiction and incarceration issues.

Today, his journey from “felon who couldn’t leave the country” to headlining major tours and award shows is a big part of why he’s such a talked‑about, trending figure online.

TL;DR: Jelly Roll was in prison largely because of an aggravated robbery with a gun over weed when he was 16, plus repeated drug and related offenses in his teens and early 20s, before turning his life around through music.

Information gathered from public forums or data available on the internet and portrayed here.