Where Have All of Diddy’s Bad Boys Gone? (To Prison, Mostly)


Sunday, April 28th, Bad Boy Records presents its Becoming King tour at the Studio at Webster Hall with recent signee King Los. With potential new members about to come out and play as well as the likes of MGK currently making an impact, what better time than now to revisit some of the Bad Boys of yesteryear and find out what they’re up to today? Take that, take that.

Craig Mack
“Flava in Ya Ear Remix,” 1994
The Bad Boy era began with the “B.I.G. Mack” double shot of the Notorious B.I.G.’s classic album Ready to Die alongside Craig Mack’s Project Funk the World. While the former has since become rightly heralded as one of the genre’s finest hours, Mack’s primarily remembered for the remix of his “Flava in Ya Ear” single, which popularized the mixtape-posse cut-style remix of having a series of established and up-and-coming artists contribute guest verses over the original hit’s beat.

While Mack left the label shortly after for a few independent releases, Bad Boy did tease a Craig Mack comeback in 2001 as Mack not only began once again popping up for quick cameos in Bad Boy videos, but even landed a guest verse on the remix of G-Dep’s “Special Delivery.” Mack made headlines once again last year when a video surfaced of him as a member of South Carolina’s Overcomer Ministry, an alleged religious cult promoting the abandoning of material goods and communal farm living, lead by controversial radio preacher Brother R.G. Stair. We’re serious.

“Feels So Good,” 1997

Kanye West’s all-time favorite rapper, Ma$e, was Puff’s right-hand man through the bulk of Bad Boy’s glory years. From setting off the iconic “Mo’ Money, Mo’ Problems” to his own landmark “Feels So Good” single, Ma$e’s presence behind the mic helped define the “shiny suit era.” During his original Bad Boy tenure, the one-time Murda Mase of Children of the Corn (which also gave us Cam’Ron and Big L), also assembled short-lived Harlem rap group Harlem World (featuring his brother Blinky Blink and sister Baby Stace) and a sophomore album in Double Up, released two months after he announced his retirement from rap to pursue being a pastor.

Of course, no rap retirements last forever, and Ma$e soon began reemerging in and out of the spotlight with the regularity of Carmen Sandiego. First returning on Bad Boy in 2004 with the “Kotter”-sampling “Welcome Back,” Ma$e attempted to reconcile his spiritual-side with his jiggy-side on Bad Boy’s more morally-aware release. There were also rumors around this time that Ma$e was being courted by Dipset, which somehow evolved into a beef with Cam’Ron and Jim Jones. But then, since nothing in life makes sense, Ma$e spent a chunk of the mid-2000s riding with G-Unit and releasing the Crucified 4 The Hood: 10 Years of Hate mixtape with DJ Whoo Kid. With the business-side of things never panning out for an official Ma$e on G-Unit album, Ma$e vanished once again. It wasn’t until 2009 when Ma$e bounced back, citing Michael Jackson’s death as renewing his interest in recording, as he began contributing verses to hot R&B records. After another public dispute with Diddy, Ma$e disappeared yet again until resurfacing last year on Kanye West’s Cruel Summer and a Wale remix with the news that, for the first time officially in 16 years, he was off Bad Boy. So that’s changed, as has his limp.

Black Rob
“Whoa,” 2000
It’s funny to think that in the years before Dr. Dre’s Detox became the go-to “When’s it coming out?” rap joke, Black Rob’s debut Life Story was one of rap’s most highly anticipated delayed releases. Finally released in early 2000, Rob’s signature song “Whoa” and its extensive cameo-filled remix became one of the year’s undisputed biggest hits. Rob was also viewed by critics as the artist who would likely lead a post-Biggie post-Ma$e Bad Boy into the new millennium. This seemed likely as Rob would also appear alongside Diddy on “Let’s Get It” and “Bad Boy 4 Life.”

Sadly, Rob was hindered from recapturing his “Whoa” success due to a few health and legal issues. He spent most of the early 2000s sidetracked with an alleged kidney ailment, and then, in 2004, served six months for failing to pay child support. Shortly after his release, he was arrested for burglarizing a New York hotel and, after failing to show up to court, was sentenced to seven years in prison for grand larceny in 2006. Released in 2010, Rob signed to New York hip-hop staple Duck Down Records and made it clear he wants nothing to do with his former boss.

“Special Delivery Remix,” 2002
Like Rob, G-Dep was another Bad Boy artist seemingly being groomed to lead the label into its next incarnation. With an underground favorite in “Head Over Wheels” under his belt, G-Dep had a few noted guest verses before his own hit “Special Delivery” propelled him, and the Harlem Shake, into the rap stratosphere. Sidetracked by his addiction to PCP, G-Dep’s time in the spotlight was short lived. He returned to rap’s consciousness a decade later in December, 2010 when, in an effort to clear his conscience, he turned himself in for a 1993 shooting that wound up killing 32-year-old John Henkel. Currently sentenced to serve the minimum 15 years for murder, G-Dep is looking to appeal.

“How You Want That,” 2003
Also running into surprising legal troubles in recent years is Loon. Debuting at the start of the decade as the featured rapper on a series of Bad Boy’s R&B singles, Loon finally released his solo debut in 2003. Backed by the singles “Down For Me” and “How You Want That,” it was clear Bad Boy hoped Loon would successfully recapture a female audience for the label. While Loon did find chart success, he soon parted Bad Boy and released a handful of independent albums, including a duet with G-Dep.

Loon re-emerged in the summer of 2009 confirming the rumors he had converted to Islam. Now named Amir Junaid Muhadith, he claimed his Bad Boy days were over and that he was “now what you would call a ‘Good Boy.'” This spiritual change of heart only made things more shocking when he was arrested in Belgium in 2011 for three-year-old drug trafficking charges he faced for allegedly distributing heroin in North Carolina. After several months of being detained in Belgium, Loon was extradited to the United States last summer. He is currently still in prison with a trial set for this July.

“Bad Boyz,” 2000
Also at the cross-sections of legal trouble and spiritual rebirth was Bad Boy rapper Shyne. While the other artists mentioned made their big debut on a collaboration or a break-out single, Shyne became a hot topic of discussion first for his alleged involvement in a December 1999 New York nightclub shooting that also drew Diddy and then-girlfriend Jennifer Lopez under heavy legal and media scrutiny. The fact that Shyne’s debut single “Bad Boyz” wasn’t sent to radio until nine months later kept the shooting inseparable from his work. While the incident did give him a certain degree of controversy and credibility, his run in the limelight would be brief as within a year he was sentenced to almost a decade in prison.

While jailed, Shyne signed with Def Jam to release his sophomore Godfather Buried Alive release which, although a chart success, in terms of rap-albums-rushed-due-to-impending-jail-time-and-partially-completed-over-the-phone, it wasn’t regarded as fondly as Mac Dre’s Back N Da Hood. Shyne was released from prison in 2009 and then almost immediately was deported to his native Belize. Notably converting to Orthodox Judaism during his prison stint, he’s continued his studies and now lives in Jerusalem as Moses Michael Levi. While he’s collaborated with Matisyahu, contributed an outro to Lil Wayne’s Tha Carter IV and has been seen with Diddy and Kanye during Paris’ Fashion Week, Shyne’s spent most of his time picking feuds with seemingly everyone who will listen, including Rick Ross, Kendrick Lamar and The Game. While the past few years have come with “confirmation” that he’s been signed to both Def Jam and Cash Money, it’s uncertain as to whether or not Shyne will even release a proper third album, let alone where it will end up.

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