There are many styles of hip-hop, but none more notorious than gangsta rap. Popularized in the '90s thanks to the hardcore rhymes penned by artists like Ice-T, Dr. Dre, and Ice Cube, the genre has been vilified by everyone from parent groups to politicians, who have argued the violence, misogyny, and promotion of street culture represented in rap lyrics is detrimental to society.
Of course, the flip side of that argument is that gangsta rap, and any form of hip-hop, really, is merely the artistic expression of the culture in which the artists live, and no matter how ugly it may seem to an outside observer, rapping about it is certainly protected under the First Amendment.
Where this whole thing gets dicey is when rappers actually live the violent, criminal lifestyles depicted in their songs, partaking in activities ranging from drug dealing, pimping, misusing firearms, and even attempting and/or committing murders. The result of keeping it that real, so-to-speak, is a long list of rappers who have died, been injured, or were incarcerated. We're dealing with the latter here, and even more specifically, the ones who are still doing their time. These are the rappers who are currently in jail.
Kodak Black's back in the slammer
Dieuson Octave is the south Florida rapper known as Kodak Black. As of this writing, he's only 20 years old, and already serving a 364 day sentence for gun and drug possession charges related to an Instagram video "that appeared to show people using marijuana and holding a handgun near an infant," according to ABC 10 Local News.
But that's really just the tip of the iceberg for the "No Flockin" rapper, who in the two years prior has been charged with "robbery, false imprisonment, fleeing a law enforcement officer, possession of a firearm by a delinquent," as well as sexual assault and a house arrest violation for leaving without permission to go to a strip club, where an employee accused him of assaulting her.
Some of those charges were dropped or pleaded down, but at one point, Black was facing a 55-year prison sentence. In April 2018, TMZ reported that even more charges from the Instagram video arrest had been dropped, meaning the embattled rapper could be out of jail as early as October 2018. However, he's still awaiting trial for the aforementioned sexual battery case for which he could receive a "maximum sentence of 30 years in prison" if he's found guilty.
In other words: It's a lot. Kodak Black is in jail for a lot, and his days dealing with the legal system don't seem to be anywhere close to being over.
Apparently that whole Ruff Ryders thing was no joke
By the time rapper DMX, whose real name is Earl Simmons, was sentenced to one year in prison in March 2018, his criminal history was already so extensive and varied, it was amazing that he was still a free man at that point. In 2010, the Daily Beast cited his 13 previous arrests "for everything from felony drugs charges, cocaine possession, criminal impersonation, and reckless driving and parole violation."
By 2016, and many more arrests later, Simmons' ruff ryding ways nearly cost him his life. According to TMZ, he was found unresponsive in a Yonkers, N.Y. Ramada Inn parking lot where one witness said that he "ingested some sort of powder before lapsing into unconsciousness." Simmons denied any drug use, and cited a recent bout of bronchitis for the collapse.
Fast-forward to January 2018, when Simmons added financial crimes to his colorful criminal resume, although you could technically count under that category the six months he served in 2015 for "failing to pay $400,000 in child support." Anyway, Simmons landed back in the clink for violating probation in a tax evasion case, according to TMZ. That case eventually ended with his March 2018 guilty plea to avoiding paying taxes on $1.7 million, earning him another year behind bars.
At the sentencing hearing, Simmons' lawyer "played part of Simmons' 1998 song "Slippin'" in the courtroom," according to Reuters, in an attempt to explain his client's troubled past. It was an interesting move, but we think we have a better suggestion for next time: "I'm Sorry," by Brenda Lee. Come on, admit you're dying to hear him cover that now.
How could adding 'murda' to your name possibly go wrong?
Brooklyn rapper Ackquille Pollard adopted the handle Bobby Shmurda when he and several lifelong friends formed the rap crew, GS9. According to GQ, the crew became official in March 2014 and it didn't take long for Pollard to become the breakout star of the group. The viral success of his song "Hot N****a" and the accompanying "Shmoney Dance" that went with it got the attention of stars such as Rihanna, Beyoncé, and Taylor Swift, as well as record labels who scrambled to sign him.
Unfortunately, police believed that GS9 also operated as a faction of the infamous LA-based Crips gang, also known as G-Stone Crips, which resulted in a wide-ranging criminal conspiracy investigation that lead to a December 2014 sweep during a recording session at Manhattan's Quad Studios. Using an indictment built largely on intercepted phone communications between GS9 members — in which they allegedly made coded references to drug dealing, shootings, and murders — the NYPD arrested Pollard and 14 others. "The investigation involved violent incidents in Brooklyn that include shootings and narcotics traffic," a spokeswoman for the Office of the Special Narcotics Prosecutor told the New York Daily News.
Pollard's specific charges, however, related only to felony gun possession charges. He copped a plea deal, accepting a seven-year prison term and waiving his right to an appeal, according to Complex. Pollard vehemently disputes the charges, alleging that lying cops railroaded him and that he got a raw deal when his trial was moved from Brooklyn, because in a Manhattan court, the jury was always going to believe "white people with badges" over "this black kid talking about shooting s**t up."
Killa Kam should konsider switching to kredit kards
In March 2018, British rapper Cameron Wright, known as Killa Kam, was sentenced to six years in jail after pleading guilty to "being concerned in the supply of heroin and cocaine," reported Gloucestershire Live. Though police did not actually catch Wright with drugs on him, they intercepted his "Jay Line," which was a phone he used to allegedly send "3,700 text messages to more than 100 customers." Wright allegedly managed "the supply chain" between Birmingham and Cheltenham, the profits from which he may have flaunted in a music video where he showcased wads of cash.
Wright's defense attorney, Jason Coulter, argued that Wright turned to drug-dealing after he was unable to find employment following a previous jail stint he served for similar charges back in 2015. Coulter argued that in his desperation to pay back fines associated with that conviction, Wright was "lured back into it … not for glamour this time, but for dull necessity."
The sentencing judge wasn't convinced, telling Wright, "It seems unlikely that you now care about the lives ruined through the supply of class A drugs." Maybe in his next video, Wright should show himself filling out job applications and awkwardly turfing it in interviews.
When life imitates violent art
RondoNumbaNine was a rising star in Chicago's "Drill scene," a sub genre of gansta rap that, according to HuffPost, rose to prominence in the Windy City in the early 2000's. Drill quickly became something of a flashpoint for debate over whether its controversial lyrics — typically involving "gangs, guns and drugs" — were "influencing the violence plaguing Chicago."
Rondo, aka Clint Massey, contributed most notably to Drill with his 2013 hit, "Hang Wit Me," which features lines such as, "These rappers they really rappers, I am just a savage who doesn't have any remorse" and "Catch a n****a saying tooka Gang then we gone murder you." Perhaps unsurprisingly, Massey became an object lesson in the debate over Drill lyrics when he was sentenced to 39 years for his involvement in the 2014 shooting death of cab driver Javan Boyd.
According to the Chicago Sun-Times (via XXL), Massey, then just 17-years-old, and an accomplice named Courtney Ealy, who was also a rapper who went by the name Cdai and was just 19-years-old, shot Boyd multiple times as he sat in his car outside an apartment complex while "waiting for a customer." Boyd's murder was allegedly a retaliation "for an earlier shooting."
For his part in the murder, Ealy was sentenced to 38 years in prison, effectively bringing an end to both of the young mens' rap careers. But who knows? Maybe by the 2050's hip-hop will have invented a new sub genre exclusively for nearly 60-year-old emcees who reportedly threw their lives away as teenagers to glorify gang life.
A prophetic felon
Joining the illustrious crowd of rappers who conspicuously implicated themselves in crimes via their own lyrical admissions is Montana Millz. The Bronx-born rapper, whose real name is Michael Persaud, released tracks such as "Sell Drugz" and "Feds Watching" before he was arrested for — you guessed it — selling drugs.
Persaud got busted twice for trafficking heroin, first in Lebanon, Pa., after he allegedly dealt to an undercover cop which resulted in a raid on his hotel room that yielded "70 grams of bulk heroin" that had "an approximate street value of $11,500," according to the Lebanon Daily News. The second time was in Rhode Island, not long after the Lebanon bust, when Persaud once again dealt to a plainclothes detective, which resulted in another raid and seizure of several illicit drugs.
In January 2018, Persaud pleaded guilty before a Rhode Island judge to "seven counts of drug distribution and possession" and received a three-year prison sentence, reported NBC Turn to 10. He didn't fare so well a month later in Pennsylvania when the judge there handed him a sentence of eight to 30 years, which will serve consecutively with his prior sentence. Ouch.
If only he'd written songs with titles like "Got a Job," "Learned my Lesson," and "I Swear This Will Never Happen Again, Your Honor."
Do these guys know how video works?
Convicted felon Ricardo Burgos, who raps under the handle Nation, apparently either wasn't aware or didn't care that he was no longer allowed to possess firearms when he brandished two of them in a music video in Deerfield, Ill. in January 2016. According to CBS Chicago, Burgos was arrested later in the day in possession of "a .45-caliber semi-automatic pistol," at which point he was charged with "one count of illegal possession of a firearm by a felon and one count of distribution of a controlled substance," the latter of which stemmed from a 2015 arrest.
Making matters even worse, although not necessarily adding to his specific legal troubles, Burgos had spit lyrics in his music "about selling drugs, committing acts of violence, and disrespecting law enforcement."
The Associated Press reported that Burgos was a member of a violent Chicago-based gang known as the Conservative Vice Lords, which perhaps figured into the sentencing judge's decision to hand down the surprisingly harsh term of 188 months. Yeesh. For that kind of time, we sincerely hope waving those guns around in that video looked super dope.
More than a decade locked up over some bling
California rapper Billy "Wild Bill" Shaffer Jr. lived up to his rap handle when he shot and killed Connie M. Sowels III outside of an Oakland nightclub on Oct. 1, 2014, according to the East Bay Times. Shaffer, who also raps under the alias Billy Bankroll, claimed he was acting in self-defense during a scuffle between himself and Sowels over a gold chain.
The jury believed Shaffer and acquitted him on the charges of "first-degree murder, second-degree murder, and voluntary manslaughter," which could have landed him behind bars for far longer than the 13 years he got for his conviction on the remaining charges of involuntary manslaughter, as well as "using a firearm and being a felon in possession of a firearm."
Shaffer reportedly "cried tears of joy" over the court's decision, but we're wondering if there was a hint of bitter irony mixed in there since this is a guy who once rapped "check my track record, never no sucker s**t" on the 2013 song, "Tell Da Truth." No suckers in jail, we guess.
Pimpin' ain't easy...or legal
Richmond rapper and fledgling pimp Idris B. Jamerson, aka Drissy Bo, found himself swapping the recording studio for the cell block after he was sentenced to four years in prison in November 2017. Six months earlier, Jamerson sealed his fate when he reportedly recruited a woman on Instagram and began selling her services via shady websites that advertise prostitution, reported the East Bay Times.
Thanks to a sting arranged by the Vacaville Police Vice Unit and FBI Violent Crime Task Force, Jamerson was apprehended on his way to deliver the woman to a prospective "customer." Upon his arrest, police recovered text messages that indicated the nature of the pair's exploitative relationship, including Jamerson giving the woman consent to buy food using the money she earned, the East Bay Times reported. In addition to the text messages, some of Jamerson's music was even used against him in court.
We're not certain which songs were played for the court, but Jamerson was the co-auteur of the questionable track, "Price Tag," which features cringeworthy lines such as "Put the b***h on a plate wit a price tag" and "That's why she get this money and she bring it right back." In the interest of full disclosure, we should also say that we don't even know if Jamerson is the one who uttered those lyrics, however his name is on the song, so he has to own that. Even the janitor in the recording studio that day probably feels guilty being associated with that mess.
Freed Meek Mill
We're ending on what is sadly the most positive note we could find. Philly rapper Robert Rihmeek Williams, aka Meek Mill, was sent back to prison for two to four years in November 2017 after violating his probation twice that same year. According to Billboard, Williams' long history with the court system started in 2008, when he was jailed for the first time for bringing a gun to a grocery store.
That charge led to a five-year probation term, which has since been extended through violations and further plea agreements, like in 2014 and 2016, when Williams was hit with violations for performing outside of Philly without permission. Most of the times Williams went before the court, he faced the same officiant, Judge Genece E. Brinkley.
By 2017, Brinkley was apparently done with Williams' repeated violations, so she told him, "I gave you break after break, and you basically just thumbed your nose at this court," reported Philly.com. Upon his sentencing, an outpouring of celebrities, including Jay-Z, Kevin Hart, and even New England Patriots owner Robert Kraft, vocally championed Williams, even tying his name to a movement — Free Meek Mill — seeking to overhaul the entire probation and parole system in America. How is any of that positive, you may ask? Great question.
Aside from the kind, but relatively useless support from celebrities, Williams attracted another powerful ally: Philadelphia District Attorney Larry Krasner, who granted Williams a re-trial after questioning the "credibility" of the arresting officer in Williams' original case. On top of the re-trial, Williams' legal team also appealed to the Pennsylvania Supreme Court in order to circumvent Brinkley's refusal to grant the rapper bail. The move worked, and he was immediately released on "unsecured bail" on April 24, 2018.
Granted, Williams still awaits trial on his probation violation charges, but for now, he's a free man. Now, that's something worth writing a song about.
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