Longest Prison Bids in Hip-Hop History

It doesn’t take much to get caught up in the mix. When you’re a high-profile artist who comes from a lifestyle of actual street activity or the glamorization of it, you’re even more prone to be a target by the police at all times. And unfortunately, many of rap’s most popular faces and names have done pretty lengthy bids in the can. XXL takes a look at which artists had long prison bids and how their run-ins with the law occurred.

There are a good amount of artists who have done their time but have since walked free. Take for example, JT of the City Girls. Right as the duo was rising in 2018, JT was sentenced to two years in prison for scamming and spent the latter half of her bid at a halfway house. Before 42 Dugg was dropping bars in the booth, he spent some time behind them as well. Dugg spent over six years in the can from 2010 to 2017 for carjacking and firearm charges.

Some rappers got trapped and slammed with RICO laws as well. Bobby Shmurda and Rowdy Rebel famously got arrested together on a slew of charges, alongside their other GS9 affiliates in 2014. Bobby and Rowdy have regained their freedom over the last couple of years. A similar situation happened with 6ix9ine in 2018, who aired out everyone he could offer to reduce his sentence drastically as he was looped into the crimes of the Nine Trey Bloods gang. The coronavirus pandemic is actually what trimmed some time off his sentence.

To celebrate their return to the real world, it’s in character for a first day out song to follow. With that being said, Gucci Mane likely comes to mind. He did a bid in 2009, for violating his probation and then again in 2014, for being caught with two firearms as a felon. The list goes on. There are dozens of other rappers that have served or are serving prison sentences. You can read more details about who and why below.