Hip-Hop sure does love a gangster. Dating back to the emergence of flicks like Scarface to go along with the ’80s crack epidemic, rappers have almost always been criminally minded in one way or another. As the industry continued to grow throughout the ’90s and ’00s and artists borrowed from the hustler aesthetic, true-to-life gangsters began to bum-rush the game on the business side, sometimes using the same tactics that got them their rep in the first place.

Kevin Chiles

Before Dame, Biggs, and Jay made us fall in love with the concept of going from hustlers to execs, Kevin Chiles (who is also the husband of Don Diva founder Tiffany Chiles) was the real deal. A noticeable presence during early ’90s the Jack The Rapper conventions alongside luminaries such as Suge Knight and a young Sean “Puffy” Combs, Chiles had all the makings of a future young mogul.

But as the Big Boss Records CEO was about to obtain a national distribution deal for his label, the feds swooped in with a indictment against Chiles on kingpin charges, thus halting his dreams of going from packs to raps. Legend has it that the feds actually tried to sabotage his record deal out of fear of Chiles’ getting away from their clutches, as he had amassed a Stringer Bell-esque portfolio of legit success aside from the hustle. With that said, f*ck the police.

Chaz Williams

Before Steven Soderbergh’s Oceans movie series made bank robbing fashionable, there was Chaz Williams. Williams was a brazen bank robber known for his prison escapes and countless shoot-outs with the law. When one particular robbery went awry, resulting in a security guard catching a gunshot wound to the head, Williams’ string of luck ended and he was sentenced to a total of 95 years. After obtaining degrees in business and knocking his original prison sentence down to 15 years via appeals, Chaz came home looking for a new lease on life through the music game.

Staying close to his Jamaica, Queens roots, Williams had a hand in molding the career of a young 50 Cent, once managed Foxy Brown and his Blackhand Entertainment franchise player Grafh amongst others. A mainstay behind the scenes, Chaz remains militant with his independent approach to the game. And, odds are he’s probably helped your favorite rapper get his jewelry back somewhere along the line.

Michael “Harry-O” Harris

While the bulk of the credit goes to Dr. Dre and Suge Knight for Death Row,s ascension to the top of the rap world, there was another shadow lurking in the wings with a major part in the label’s success. That man was Michael “Harry-O” Harris, a former Bloods member incarcerated on kingpin charges. As the story goes, Harris reportedly fronted Suge Knight $1.5 million through the help of his wife and attorney, David Kenner, in exchange for a 50 percent stake in the company.

Because of a lack of communication between him, Kenner, and Knight after the initial success of Death Row, Harry-O advised his people to save and document all paperwork related to the partnership. Following years of non-payment and mistrust, Harris’ wife sued Knight, eventually getting a judge to order Suge to pay $107 million in damages.

Harry-O was released from San Quentin Prison on October 11, 2011 after serving 23 1/2 years on his original sentence.

Jacques “Haitian Jack” Agnant

“Haitian Jack’s” name definitely rang a few bells and shook up a few souls during his reign in the industry. Hailing from the streets of East New York in Brooklyn, Jack, real name Jacques Agnant, made his entrance in the game through intimidation and charm, acting as a hanger-on and confidant to various superstars. After allegedly being involved in the infamous Tupac/Quad Studio shooting, Jack got in good favor with fellow Haitian Wyclef Jean before being nabbed by the Feds and agreeing to become a music industry informant.

After heading to Beverly Hills to continue his reign of terror (albeit under Federal supervision), Jack lost it after being disrespected by some Black Mafia Family members and shot-up one of the thugs in the middle of the club. This lead to his eventual deportation, thus ending his legendary strong-arm tactics, as far as we know.

Calvin “Klein” Bacote

“I never felt more alive than riding shotgun in Klein’s green 5, ’til the cops pulled guns” – Jay-Z, “The Allure”

Brooklyn Don Calvin “Klein” Bacote was a titan on the streets during the mid- to late-’80s, reportedly ruling the Red Hook and Marcy Housing Projects with an ironfist. Before being sentenced to a lengthy jail sentence on federal drug charges, legend has it that Calvin Klein was once criminally involved with fellow Marcy legend Jay-Z and actually took the rap for an attempted murder charge, allegedly paying $50,000 to keep the promising MC out of the laws reach.

After lending credence to Jay’s street cred in interviews, Klein had hopes of being taken under his former protege’s camp following his release. Feeling that Jay “should pay homage” to a guy whose “life he sampled” for musical inspiration, he felt entitled to a spot in cushy Jay’s camp, but Jigga had no such plans. Although his relationship with Hov went awry, fellow felon Akon intervened and gave Klein a high ranking position in his Konvict Music venture, leaving the hard rock with a soft landing after the pen.

Demetrius “Big Meech” Flenory

Arguably the most ubiquitous name on this list, BMF is synonymous with when the streets and industry collide. From the brazen billboards overlooking the city to being publicly associated with Young Jeezy, Demetrius and brother Terry Flenory were definitely making a name for themselves in Atlanta around 2000, their high profile ways raising the eyebrows of everyone from your casual rap fan to the feds.

Their excessive flash of wealth and high-priced toys without a viable commercial artist on their roster didn’t help their causes with them alphabet boys, as they swooped down with and indictment that included everyone from flagship artist Bleu Davinci to Jacob The Jeweler. As brief as their ride on the top was, it will remain almost mythical in the minds of some, as their ‘the world is mine’ attitude resonated with the spirit of the culture, but cost them their freedom in the end.

Charles “Chilly” Patton

When the Roc-A-Fella dynasty was in it’s prime, Jay-Z once recruited a young Chi-Town lyricist named Lupe Fiasco to potentially join his stable of spitters. Even though Fiasco would eventually turn down Hov’s offer, the man responsible for pulling the strings behind the scenes and making such meetings happen was Charles “Chilly” Patton. But along the ride to the majors there was a bump in the road, in the form of criminal conspiracy charges involving drug distribution.

In a 2003 raid of Patton’s home, police found a key to a storage unit, which allegedly contained six kilograms of heroin. During his trial in 2007, prosecutors presented a recorded phone call between Lupe and Patton discussing “cutting up whole reds and whole yellow ones,” street slang for packets of heroin, but Fiasco insisted they were in fact discussing music during the conversation.

While Fiasco was eventually found of no wrongdoing and still continues to support his mentor to till this day, Patton didn’t fare as well, being sentenced to 44 years in prison.

James “Jimmy Henchman” Rosemond

With a nickname that was definitely earned, Rosemond was a terror on the streets and in the prison system. Early on, Henchman made a name for himself as one to be respected and feared, running Rikers Island’s notorious C-74 Juvenile Unit, known for housing the most rotten seeds in the Big Apple (including the original 50 Cent). Entering the music industry, Jimmy hustled his way into a credible career as a manager, overlooking the careers of artists such as The Game and Sean Kingston as the CEO of Czar Entertainment.

While it looked like Rosemond had overcome his criminal past, revelations came to light that in addition to running a cocaine distribution network and committing murder-for-hire, Henchman also allegedly admitted to involvement in the 1994 shooting of Tupac at NYC’s Quad Studio’s. It is said that Henchman, who met Tupac with Haitian Jack while Pac prepped for his role in Above The Rim, grew jealous over Shakur’s celebrity. After Pac made negative comments directed towards Rosemond while on trial for rape, Rosemond reportedly felt that the rapper “had to be taught a lesson.”

Henchman later denied making those statements or admitting his involvement, but the proof is in the pudding and it’s safe to say Rosemond’s run in the rap game is all but over. In June 2012, he was arrested in NYC on federal cocaine distribution charges and faces life in prison.