Gang in Real Life: These Rappers Went to Jail For Being Gangsters - Page 29
Source: Donaldson Collection / Getty
Updated: May 15, 2025, 4:08 p.m.
R&B heartthrob Chris Brown is reportedly in trouble with the law again.
The Sun reports that the “Residuals” singer was arrested outside of the Lowry Hotel in Manchester, England this morning. The arrest at 2 am local time is for an alleged incident that happened at Tape nightclub in Mayfair, London in February 2023.
Brown was held on suspicion of causing grievous bodily harm to music producer Abe Diaw. Diaw claims that Brown smashed him over the head with a bottle of Don Julio 1942 tequila, unprovoked, and then kicked him. “He hit me over the head two or three times. My knee collapsed as well,” Diaw told The Sun.
From Diddy to Tupac, Some Of Your Favorite Rappers Have Done Real Time Behind Bars
It’s true, some of your favorite rappers may have gone to jail. And some of them were arrested for being gangsters.
Others? Perhaps just wrong place/wrong time.
The thing is, the term gangster is subjective. A person doesn’t necessarily have to be in an official gang to do ‘gang-related activity’.
Love it or hate it, certain sectors of rap music are solely predicated on being tough. It’s not just about the words you say, but the bravado with which you say them.
And trust, it’s not just the artists who understand the dynamic of their reputation when it comes to their record sales. The record labels understand this as well, almost to a fault.
Gangsta rap started in the 80s. Acts like Ice-T and NWA held no punches, skewing the genre with its no-holds-barred approach to rhyming and telling stories. Over the last 30-plus years, that style has evolved. It’s hardened, to a point where entire generations of hip-hop fans don’t want to hear it if it’s not about shooting or getting shot.
Cassie Takes Stand At Diddy Trial, Says Freak Offs Lasted 4 Days
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But, here’s the problem – it’s hard work being a lifelong criminal
Being a gangster in 2025, as it relates to rap music, doesn’t always mean that that person is tied to an organized criminal organization. It’s often simply associated with a way of life.Cassie Breaks Her Silence On P. Diddy Assault Video
With that said, let’s take a look at some of these rappers who weren’t able to avoid the eye of the law for as long as they’d hoped.DON’T MISS THE LATEST NEWS! JOIN OUR TEXT CLUB! TEXT ‘Z1079’ TO 71007!
Keep scrolling to see some wild examples of rappers who went to jail for being gangsta.1. Diddy
Diddy is facing more than two dozen charges, and his trial just kicked off earlier this week.
3. Lil Durk
Lil Durk is currently in jail on murder-for-hire charges.
5. Young Thug
Young Thug, real name Jeffery Lamar Williams, was arrested back in May for suspicion of gang involvement and conspiracy to violate the Georgia criminal racketeering law. He’s allegedly the leader of Young Slime Life (YSL), which has reported ties to the Bloods gang. Fellow Atlanta rapper Gunna was picked up as well. Yesterday (August 10) Thugger was indicted on additional charges that related to gang activity, plus drug and firearms violations.
7. Lil Wayne
Dwayne Michael Carter, Jr., otherwise known as Lil Wayne, has never been shy of admitting to his Blood affiliations. In March of 2010, Wayne began an 8-month bid on Riker’s Island for weapon possession. In January 2021 he was pardoned by former president Donald Trump after almost getting sentenced to 10 years for a different weapon case.
9. Kodak Black
Rappers and their guns. In 2019, Kodak was sentenced to 46 months in prison for fabricating information on gun applications. He’s also affiliated with the Zoe Pound gang.
11. T.I.
T.I. has had several run-ins with the law. With several of his arrests coming as a teenager, he was noticeably convicted of possession of crack cocaine with the intent to distribute in 1998. He was later sentenced to three years in prison for violating his probation. T.I. has never confirmed being in a gang, though his ties to street life, especially early in his life, are well documented.
13. Tupac Shakur
While Tupac was a known affiliate of the Bloods gang, he wasn’t a direct member. Still, folks believe that his ultimate demise – getting gunned down in a Las Vegas drive-by – was the result of him getting into a scuffle with a member of the Crips gang earlier that day. In 1995 he served eight months for alleged sexual abuse.
15. DaBaby
DaBaby, for years, has denied having associations with any gangs. While that may be true, everyone knows he’s as ‘gangsta’ as they come. He is, after all, the only person on this list to have been proven to kill a man.
He has had several very public run-ins was law enforcement. Per his arrest record, he’s been jailed for driving with a fake license, drug possession, and possession of an illegal firearm. In early 2021 he was jailed in LA for taking a loaded gun into a store on Rodeo Drive.
17. Bobby Shmurda
Bobby Shmurda, who was born in Miami and raised in Brooklyn, was convicted after it was proven that he was the driving force in a gang called GS9. He was released from Clinton Correctional Facility in February 2021 after doing over six years behind bars.
19. Tekashi 6ix9ine
A member of the Nine Trey Gangsters, Tekashi 6ix9ine pleaded guilty to several crimes in December 2019. After facing life in prison, he famously snitched on fellow gang members, reducing his potential life sentence down to less than two years. He was later released early because of the pandemic.
21. Jay-Z
While Jay-Z has a rags-to-riches story for the ages, and he’s well known to have surrounded himself with hustlers since a young age, he’s never been proven to be in a gang. In April 2001, he was arrested for gun possession. He also faced up to 15 years for stabbing a producer in 1999 but managed to only get 3 years probation instead.
23. Snoop Dogg
Snoop Dogg is a former member of the Rollin’ 20s Crips. While he was acquitted of murder in 1996, there were several other instances that did involve Uncle Snoop sitting in jail. He’s been charged with cocaine possession, gang affiliation, and marijuana possession over the years.
25. Akon
Akon, real name Aliaune Thiam, was once in and out of jail for his role in a car theft ring when he was a youngster. Though he did admit he was capping about running the organization and doing 3 years in prison behind it.
27. Eve
Ruff Ryder queen Eve was arrested for a DUI in 2007. Not gang-related, but Eve has often shared her regrets over how she lived as a young adult.
29. Remy Ma
In 2007, Remy Ma shot Makeda Barnes-Joseph at a Manhattan nightclub after discovering $3,000 missing from Barnes-Joseph’s purse. She served six years and was released in 2014.
31. C-Murder
In 2002, Miller was arrested in connection with the murder of 16-year-old Steve Thomas. He was sentenced to life in prison on August 14, 2009. Miller is serving his sentence at the Louisiana State Penitentiary.
33. YFN Lucci
Rapper YFN Lucci (real name Rayshawn Bennett) was in jail for violating Georgia’s Street Gang Terrorism an Prevention Act. He was arrested in 2021 as part of a gang investigation
35. Tsu-Surf
Battle rapper Tsu-Surf was sentenced to five years in prison for his role in a RICO case. Surf pleaded guilty to Racketeer Influenced and Corrupt Organizations (Rico) conspiracy charges.
Gang in Real Life: These Rappers Went to Jail For Being Gangsters - Page 29 was originally published on zhiphopcleveland.com
