Meek Mill, Stephen Colbert
Screenshot: The Late Show

At the beginning of their interview on Thursday’s Late Show, Stephen Colbert asked rapper Meek Mill to be as succinct as possible in summing up the long legal nightmare that’s seen him imprisoned several times over the past twelve years. That’s not an easy feat, but Mill—whose battles with the criminal justice system are the subject of the upcoming, five-part Amazon documentary series Free Meek—gave it a shot, outlining how a since-overturned conviction on a gun charge when he was 19 has seen him imprisoned and placed under house arrest multiple times over the past decade, despite never being charged with another crime.

“I’ve been on probation my whole adult life,” explained the now 32-year-old Mill, who has turned his circuitous journey through the criminal justice system into a crusade for probation reform as co-chair of activist organization Reform Alliance. (Alongside Jay-Z, Van Jones, Philadelphia 76ers co-owner Michael Rubin, and, um, Patriots owner Robert Kraft, among others.) Telling Colbert that while growing up “raised in violence” in North Philadelphia meant he was “no angel” as a young man, Mill has always denied the initial charge that he pointed a gun at a police officer back in 2007. (The policeman, Reginald Graham, eventually left the force after being caught stealing money and lying about it in an internal police investigation, while another officer at the scene has said that Graham lied about Mill pointing a gun.)

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But none of those circumstances have helped Mill over the intervening years. (Nor have the allegations of inappropriate behavior—including asking for a shout-out on one of Mill’s albums—by the judge who’s been in charge of Mill’s fate, Genece Brinkley.) That’s meant that any contact with police (a non-charged infraction called a “technical violation”) has seen Mill spend various terms in prison and under house arrest, despite never being convicted of anything. (One such “police contact” stemmed from Mill popping a wheelie on a dirt bike.) Thankfully, Mill told Colbert, his long legal ordeal may finally be over. In July, Mill’s initial conviction was overturned, freeing him from a trap the rapper and activist states is all too common—especially among people of color who, unlike him, haven’t got millions of dollars and a lot of celebrity friends to aid their cause.

With his conviction overturned, Mill said that there still remains the possibility of a retrial on the now 12-year-old initial charge, but, with prosecutors saying that Graham’s suspect testimony is no longer in play, it looks like Mills’ long-overdue escape from America’s carceral state is all but ensured. And while Mill is adamant about continuing his work to aid others trapped in the same predicament, he also admitted it was also pretty freeing to sign a huge deal with Jay-Z’s RocNation to form his own Dream Chasers Records on the same day he got the good news about his case. Telling Colbert that his activism has brought him into contact with a lot of your men who, like himself, face futures seemingly rigged against them, Mill stated, “For the average person, getting a fair shot in America is extremely hard,” but that his message remains “be a leader, never let nobody mislead you and do things that you don’t want to do, and chase your dreams.”

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Free Meek premieres August 9 on Amazon.