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What Did Jelly Roll Go to Prison For?

Jelly Roll, born Jason De’Shawn Rollins in 1981, is an American rapper, songwriter, and producer from Nashville, Tennessee. Before finding mainstream success with his emotional, confessional style of hip hop, Jelly Roll spent over a decade entrenched in the streets and embroiled in the justice system. His turbulent past included robbery, drug dealing, addiction, and multiple stints behind bars. This article will explore Jelly Roll’s criminal history and the convictions that led to his incarceration.

A Life of Crime and Drugs

Jelly Roll grew up in poverty in Nashville and turned to crime and drugs from a young age. By the time he was 11 years old, he was already using and selling drugs. In his lyrics and interviews, Jelly Roll has been transparent about his past mistakes and regrets. He started using marijuana and cocaine as a preteen and eventually progressed to dealing crack cocaine as a teenager. The money supported his addiction but also put him directly in the line of fire.

Conviction History and Time Served

Jelly Roll has served three separate sentences in jail or prison. Here is an overview of his conviction history and the amount of time he served:

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DateCharge/ConvictionTime Served
1997 (age 16)Robbery3 years in juvenile detention
2003 (age 22)Drug-related charges120 days in county jail
2009 (age 28)Drug trafficking3 years in state prison

His first brush with the law came at 16 when he was charged as an adult for robbery and spent 3 years in a juvenile detention facility. In his early 20s, Jelly Roll served 120 days in county jail for drug possession and distribution charges. His lengthiest sentence came in 2009 when he was convicted of selling over 300 pounds of marijuana and spent 3 years in state prison.

Details of Drug Trafficking Conviction

Jelly Roll’s 2009 conviction for drug trafficking carries an interesting backstory. Here are more details on the events leading up to his 3-year prison sentence:

  • In 2008, Jelly Roll was still actively dealing drugs and making trips to Texas to pick up large loads of marijuana.
  • On one particular run, he rented a U-Haul truck to transport over 300 pounds of marijuana back to Tennessee for distribution.
  • Along the highway near Memphis, he was pulled over by police for a routine traffic stop. Smelling marijuana, officers searched the truck and uncovered the massive cache of drugs.
  • Jelly Roll was arrested and later sentenced to 3 years in state prison for possession and intent to distribute over 300 pounds of marijuana.
  • He has cited this trafficking bust and conviction as one of his biggest regrets and a turning point in his life.

Jelly Roll’s Reflections on His Crimes

In songs, interviews, and his autobiography, Jelly Roll has been very reflective about his criminal lifestyle and prison stints. Here are some insightful quotes where he openly discusses his past:

“I went against my moral code. I did a lot of things I ain’t proud of, like robbing people. I regret that.”

“I was dishonest, I was a drug dealer, so I was contributing to the delinquency of the neighborhood.”

“I’m ashamed of some of the things I did, but everything I did got me to the point where I could tell it and put it in my music.”

“Prison is nasty. It’s filthy. It’s grimy. Nothing about it is anything that you want to experience.”

“Prison is what separates the men from the boys. It’s a rite of passage in the streets.”

Impact on Jelly Roll’s Music Career

Jelly Roll’s experiences in jail and prison heavily influenced his music and helped shape his unlikely path to success. Here are some of the key ways prison impacted his rap career:

  • He started writing lyrics and rapping while incarcerated as an outlet and coping mechanism.
  • The raw emotions and lessons learned behind bars provided endless material and authenticity for his music.
  • His conviction history made it difficult at first to get recordings into the hands of producers or fans.
  • Serving time earned him respect and street credibility that helped his music resonate.
  • The introspection during sentence gave clarity on wanting to pursue rapping full-time once released.
  • Prison served as a turning point — he left determined to make an honest living through music.
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FAQs About Jelly Roll’s Incarceration History

How many times has Jelly Roll been to jail?

Jelly Roll has been incarcerated 3 separate times: once as a juvenile for robbery, once for 120 days on drug charges, and once for 3 years for drug trafficking.

What age was Jelly Roll when he went to jail first?

Jelly Roll was arrested for robbery and sent to juvenile detention in 1997 at the age of 16. This marked his first time behind bars.

What drugs was Jelly Roll involved with?

Jelly Roll started using marijuana and cocaine at age 11. As a teenager and young adult, he progressed to selling crack cocaine and large quantities of marijuana which ultimately led to his trafficking conviction.

Where was Jelly Roll incarcerated?

His sentences were served at juvenile detention facilities and jails around Nashville. His longest prison stint was at Northwest Correctional Complex in Tiptonville, Tennessee.

Has Jelly Roll stayed out of legal trouble since his last conviction?

Yes, since his release from prison in 2012, Jelly Roll has stayed clean, sober, and out of legal trouble while focused on his music career.

How has Jelly Roll turned his life around?

After his final prison sentence, Jelly Roll got sober, distanced himself from street life, devoted himself to music, and formed a close family with his girlfriend Bunnie. Rap success enabled him to make an honest living.


In summary, Jelly Roll served 3 separate sentences related to robbery, drugs, and trafficking convictions before emerging as a rapper. His troubled past informed his music’s raw authenticity. Prison served as a turning point for focusing on music and leaving the streets behind. Despite his regrets, Jelly Roll’s rapport and redemption through rap have made him one of music’s most compelling stories. After surviving the streets and justice system, his unlikely success story continues to inspire.

Prison Inside Team

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Welcome to ‘Prison Inside,’ a blog dedicated to shedding light on the often hidden and misunderstood world within correctional facilities. Through firsthand accounts, personal narratives, and insightful reflections, we delve into the lives of those who find themselves behind bars, offering a unique perspective on the challenges, triumphs, and transformations that unfold within the confines of these walls.

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