Gang in Real Life: These Rappers Went to Jail For Being Gangsters

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 in which you say them. 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.

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Over time, the line between rapping tough for entertainment and being a real-life gang banger – who just so happens to rap – has become blurred. Now some artists really believe that they must live the criminal rhymes that they bark over beats. But, here’s the problem – it’s hard work being a lifelong criminal. Being a gangster in 2022, in relation 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. 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.

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Keep scrolling to see some wild examples of rappers who went to jail for being gangsta.

1. 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.

2. Young Thug Arrest

3. 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.

4. Lil Wayne Heads to Sentencing

5. 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.

6. Rapper Kodak Black Jailed On Multiple Charges

7. 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.

8. T.I. Gets Probation Revoked

9. 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.

10. Tupac Defends Himself

11. 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.

12. DaBaby Talks About Unlawful Arrest

13. 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.

14. Bobby Shmurda Comes Home

15. Tekashi 6ix9ine

A member of the Nine Trey Gangsters, Tekashi 6ix9ine plead 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.

16. Tekashi Six9ine Telling on Everybody

17. 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.

18. Jay-Z Avoids Prison

19. 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.