Longest Prison Bids In Hip-Hop History - XXL Mag

Here Are the Longest Prison Bids in Hip-Hop History

XXL StaffUpdated: June 19, 2025

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It doesn’t take much to get caught up in the mix. When a high-profile artist comes from a lifestyle of actual street activity or the glamorization of it, sometimes that can lead to legal issues and being targeted by the police. Unfortunately, many of rap’s most popular faces and names have done pretty lengthy bids in the can. Here's a look at the rappers who've 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. 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. Gucci Mane comes to mind in that respect. 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. Check out the longest prison bids in hip-hop history.

See 47 of the Longest Prison Bids in Hip-Hop History

C-Murder, Max B, B.G. and more.Filed Under: 03 greedo, 42 Dugg, 6ix9ine, B.G., Beanie Sigel, big lurch, Bobby Shmurda, Boosie Badazz, Bump J, C-Murder, Cassidy, chi-ali, DMX, Drakeo The Ruler, Fat Trel, Feature, Fetty Wap, Flesh-n-Bone, G. Dep, Gallery, Gucci Mane, Icewear Vezzo, Ja Rule, JT, Kodak Black, Lil Baby, Lil Kim, Lil Wayne, Mac Phipps, Max B, Meek Mill, Mysonne, Mystikal, Ol' Dirty Bastard‬, Pimp C, Prodigy, Remy Ma, Rowdy Rebel, Shyne, Slick Rick, T.I., Tay-K, Tee Grizzley, Tony Yayo, Tory Lanez, Tupac, Turk, YNW Melly, Young BuckCategories: News

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