Catching Cases: Rappers Locked Up Too Early In Their Career

Rap and jail time have had a close relationship ever since the Fat Boys rhymed about doing time for holding up a pizza place.

Unfortunately, prison bids have stymied many promising careers over rap music's history. For every Tupac "out on bail, fresh outta jail, California dreamin'" there's five rap stars whose careers never recovered after doing time.

After recent arrests in connection with gun and drug charges, Bobby Shmurda and several members of his GS9 collective may find themselves wandering down this same path, if they're not careful (and it could very well be unavoidable judging the seriousness of the charges).

HNHH hopes the "Hot Boy" hitmaker doesn't end up in the same boat as these once rising stars....

British-born rapper Slick Rick was certainly able to have an impact before his 1991 conviction on attempted murder charges. 

The Hip-Hop Hall of Fame inductee, who is regularly credited for popularizing narrative rapping, was two years removed from his all-time classic 'he Great Adventures of Slick Rick when he shot his cousin Mark Plummer in 1990. 

He was able to release one more album, (1991's The Rulers Back), before his conviction. The album was nowhere near as successful as Great Adventures commercially or critically. Even so, the album is leaps and bounds above anything that Rick has released since his release in 1996.

The arrest has haunted Rick in other ways as well. In 2001, he was detained by INS and threatened with deportation after a cruise ship performance. 

Rick, who never became an American citizen, was vulnerable under a law that allows deportation of non-citizens who serve more than five years in prison for felony charges.

Rick spent 17 months in prison and INS continued their deportation efforts until New York Governor David Paterson pardoned Rick in 2008.

The First Lady of the Terror Squad seemed poised for a solid rap career when a shooting incident in 2007 derailed her plans.

Riding high on the success of posse cut “Lean Back” (which netted Remy a Grammy nomination and the distinction of being one of four female MCs to top the Billboard Hot 100), Remy released her debut solo album There’s Something About Remy: Based on a True Story. The album received positive reviews but sold poorly.

Remy was working on a new reality show, a female rap supergroup with Shawnna and Jacki-O and her second album PunisHER when she shot her friend Makeda Barnes-Joseph in the abdomen during an altercation outside of a Manhattan nightspot. Ma believed that Barnes-Joseph had stolen $2,000 from her.

Ma was convicted in 2008 of assault, illegal possession of a weapon and attempted coercion. She was released from prison on August 1, 2014 after serving six years.

Although there was a healthy buzz anticipating her release, with both her clout and the clout of the Terror Squad as a whole completely evaporated, it is unlikely that Ma will ever find success on the same level again.

Mystikal was hands-down the best rapper to come out of the ‘90s hip-hop scene in New Orleans. His deranged, lightning-fast verses and throwback “soul screamer” delivery was far more interesting than the work of his counterparts and the world took notice.

Mystikal went on a hot streak in the late ‘90s and early 2000s, releasing hits like “Danger (Been So Long)”,“Shake Ya Ass” and “Bouncin’ Back (Bumpin’ Me Against The Wall).”  He also scored several prominent features on Joe’s “Stutter”, Ludacris’ “Move Bitch” and Lil’ Jon’s “I Don’t Give A Fuck.”

All of that came to a screeching halt in 2004,  when Mystikal was sentenced to six years in prison for sexually assaulting his hairstylist. Since his release in 2010, Mystikal hasn’t had much success. He signed to one-time rival label Cash Money Records and released a genuinely great but largely unnoticed collaboration with English musician Mark Ronson.

Shyne’s peak was so high that it shocked the world. The Belize-born rapper was discovered while freestyling in a barbershop and quickly signed to a five-album deal by Diddy that included millions of dollars, three cars and two homes.

Surprisingly, the rapper actually made good on this contract. His debut self-titled album moved 900,000 copies and landed at number 5 on the Billboard charts. However, the rapper was involved in the infamous nightclub incident in 1999 with Diddy and then-girlfriend Jennifer Lopez in which three people were shot. Shyne was charged with attempted murder, assault and reckless endangerment. He was sentenced to 10 years in prison.

Unlike other members on this list, Shyne was able to have success while in prison, his 2004 album Godfather Buried Alive made it to the number one spot on Billboard’s hip-hop charts. After his release was a different story, though.

Shyne seems determined to burn any potential bridges back to superstardom, calling out Diddy, Rick Ross, Drake, 50 Cent and Kendrick Lamar on his most recent mixtape Gangland. The strategy has not gone well for him. The closest he’s come to fame since his release is a shout-out by Killer Mike on Run The Jewels much-lauded debut.

The Great Guwop has constantly flirted with illegality his entire career serving  many small stints in county jails in between releases of great mixtapes and classics albums like the Trap House series and The State vs. Radric Davis.  Around  late 2010, however, Gucci started making news more often for his legal troubles than his music.

Gucci has been arrested 5 times since 2010 and it’s clearly had an effect on him. Gucci has spent the last few years getting an unfortunate ice cream tattoo on his face, blowing up his successful Brick Squad collective, and attacking friends and colleagues on Twitter. Although he's been able to put out a surprising number of tracks while still locked up, we can only imagine the impact and lasting effect his career would have, were he to avoid all legal troubles to begin with.

His recent track with rising Atlanta star Raury showed promise, and he did drop off on open letter to his fans recently detailing all the changes he has planned for once he's a free man. Let's just hope he sticks to it. We won't know how his story fully pans out until his release, likely in 2016. 

Much like Gucci, DMX doesn’t have a single arrest that upended his career. The barking madman behind ‘90s smashes like “Get At Me Dog”, “Party Up” and “Ruff Ryders Anthem” just can’t seem to stay out of trouble.

Starting with an arrest in 1998 for weapons possession, the Dark Man has been arrested 13 times over the 14 years, serving several sentences. Despite selling over 18 million albums in his career, it is unlikely that Earl Simmons will ever return to the upper echelons of rap stardom.

Don’t get us wrong, T.I. has had success with his post-prison, motivational speaker rap. Paper Trail and No Mercy have serious radio hits on them.  And you can’t discount that reality TV money.

However, Clifford Harris hasn’t come within spitting distance of anything that was released during his legendary five-album run starting with I’m Serious and ending with TI vs. TIP.  The 2009 prison bid has genuinely changed T.I.’s style. It certainly didn’t affect his ability to make money, but critically-speaking T.I. is hurtin’.

Turk was more of a regional concern for the majority of his career, making a name for himself in New Orleans during stints with the Hot Boyz and appearances on Cash Money Records’ posse cuts. He broke out nationally in 2001 with the release of his Gold-certified solo debut Young & Thuggin’. His next two albums didn’t perform as well commercially, but the latter Penitentiary Chances was lauded as his strongest album to date.

Turk squandered that momentum after being convicted of felony possession of a firearm and attempted second-degree murder following a shootout with a Tennessee police officer. His final conviction came in 2006 and he was released in 2012 after 9 years in prison.

Since then he’s signed to Rap-A-Lot Records and released a mixtape on SoundCloud called Blame It On The System that you probably never listened to.

ByrdGang member and Diplomats associate probably has the least likely chance of a career resurgence out of all of these rappers.

The man who co-wrote Jim Jones hit “We Fly High (Ballin’)” is currently serving a 75-year sentence for conspiracy to armed robbery, kidnapping, aggravated assault, and murder charges stemming from a botched robbery in 2006.  

While it hasn’t slowed down his production any (Max B has released 19 mixtapes and his lone studio album since 2006), the man has far less cultural clout than even other  Diplomat also-rans like Hell Rell and J.R. Writer.

You know what I said about Max B being the least likely to mount a comeback? Scratch that.

No Limit signee and brother of Master P and Silkk The Shocker, C Murder is currently serving a life sentence for, well, murder.

Murder (nee Corey Miller) was one of the major successes of his brother Percy’s No Limit machine. He released three top 10 albums at the turn of the century, with his solo debut Life Or Death being certified platinum.

Murder has been convicted several time for fatally shooting a 16 year-old fan at a nightclub in Harvey, LA. His first conviction was re-tried after it was found that the prosecution withheld information about their witnesses criminal history. The 2009 retrial also convicted Miller, but was scrutinized after one of the jurors admitted she was berated and forced to change her vote to guilty to avoid a mistrial. The conviction was appealed, but ultimately upheld in 2011.

Lil Boosie

Boosie may be free and more popular than ever, but there's no question that his nearly 5 year incarceration hindered his career. 

Boosie had built a loyal fanbase in his hometown of Baton Rouge, and much of the South before beginning his 2 year sentence for third degree possession of Marijuana, but it certainly seemed as if he was going to jail at the height of his popularity.

Thankfully the rapper was found not guilty on charges of first degree murder, but after being hit with drug charges while behind bars, it seemed he may serve another 8 years. All the while, the legend of his music continued to spread.

Badazz' legal team was able to convince the court to drop the charges, and the rapper made it out of jail in 2014. While he lost quite a few years that could have been spent productively, this is ultimately a happy ending, with Boosie being welcomed by a bigger fanbase than he'd known before his sentencing.