The 41-year-old country singer - real name Jason DeFord - first went to jail aged 13 after being caught with cannabis and then failing to go to court.
He later served a year behind bars over his involvement in a robbery when he was 16 and the felony conviction left him unable to vote or travel internationally without restrictions.
However, he has now been granted a pardon by Tennessee Governor Bill Lee who cleared the singer of his robbery and drug possession convictions.
Lee said: "His story is remarkable, and it's a redemptive, powerful story - which is what you look for and what you hope for."
The decision to wipe away the singer's past convictions came following guidance from the Tennessee Board of Parole which voted unanimously to issue a non-binding recommendation in favour of clemency.
At a Board of Parole hearing held on Tuesday, several character witnesses spoke on Jelly Roll's behalf and he told the panel that his stint behind bar led him to his career in music.
He said: "It started as a passion project that felt therapeutic and ended up changing my life in ways I never dreamed imaginable, opening doors I never thought possible."
The pardon means the singer will now face fewer restrictions when travelling abroad and will allow him to tour outside of the US and undertake Christian missionary work.
One of the singer's convictions stemmed from his involvement in a robbery when he was 16 and he previously called it a "heinous crime" and he was glad nobody got hurt.
He told Billboard: "I never want to overlook the fact that it was a heinous crime. 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."
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