The Bad Boy era began with the Notorious B.I.G.'s classic album Ready to Die and Craig Mack's Project Funk the World. While the former has 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, with both established and up-and-coming artists contributing guest verses over the original hit's beat.
Mack left the label shortly afterward for a few independent releases. Bad Boy teased a Mack comeback in 2001, and he began once again popping up for quick cameos in Bad Boy videos, even landing 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 communal farm living and the abandonment of material goods and, lead by controversial radio preacher Brother R.G. Stair. Yes, for real.
Kanye West's all-time favorite rapper, Ma$e, was Puff's right-hand man through the bulk of Bad Boy's glory years. From the iconic "Mo' Money, Mo' Problems" to his own landmark "Feels So Good" single, Ma$e helped define the "shiny suit era." At one point known as Murda Mase and a member of Children of the Corn crew (which also gave us Cam'Ron and Big L), during his Bad Boy tenure Ma$e also assembled short-lived Harlem rap group Harlem World, featuring his brother Blinky Blink and sister Baby Stace. His sophomore album, Double Up, was released two months after he announced his retirement from rap to pursue being a pastor.
Of course, no rap retirements last forever, and Ma$e has been in and out of the spotlight. First returning on Bad Boy in 2004 with the Kotter-sampling "Welcome Back," Ma$e attempted to reconcile his spiritual-side with his jiggy-side. There were also rumors around this time that Ma$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$e spent a chunk of the mid-2000s riding with G-Unit and releasing the Crucified 4 The Hood: 10 Years of Hate mixtape with DJ Whoo Kid.
But things didn't pan out for an official Ma$e G-Unit album, and so he vanished once again. In 2009 he bounced back, citing Michael Jackson's death as renewing his interest in recording, and began contributing verses to hot R&B records. After another public dispute with Diddy, Ma$e disappeared yet again until resurfacing last year on Kanye West's Cruel Summer and a Wale remix. For the first time in 16 years, he was officially off Bad Boy. So that's changed, as has his limp.
Black Rob's debut Life Story was the Detox of its day; finally released in 2000, Rob's signature song "Whoa" and its extensive cameo-filled remix became one of the year's biggest hits. Rob was viewed by critics as the artist likely lead a post-Biggie post-Ma$e Bad Boy into the new millennium; he would also appear alongside Diddy on "Let's Get It" and "Bad Boy 4 Life."
Sadly, Rob was hindered by health and legal issues. He reportedly spent most of the early 2000s sidetracked with a 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.
Like Rob, G-Dep was another Bad Boy artist seemingly being groomed to lead the label into its next incarnation. With underground favorite "Head Over Wheels" under his belt, G-Dep dropped 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 the 1993 fatal shooting of a 32-year-old man named John Henkel. Currently sentenced to serve the minimum 15 years for murder, G-Dep is looking to appeal.
Loon also has had legal troubles in recent years. Debuting at the start of the decade as the featured rapper on a series of Bad Boy's R&B singles, he 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 capture a female audience. While he did find chart success, he soon parted with Bad Boy and released a handful of independent albums, including a duet with G-Dep.
Loon re-emerged in the summer of 2009, and 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 charge, for allegedly distributing heroin in North Carolina. After several months of detainment in Belgium, Loon was extradited to the United States last summer. He is currently still in prison, with a trial set for this July.
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 gave him a certain degree of controversy and credibility, his run in the limelight was 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 was partly completed over the phone but nonetheless a chart success. Shyne was released from prison in 2009 and then quickly deported to his native Belize. Having converted to Orthodox Judaism during his prison stint, he's continued his studies and now lives in Jerusalem as Moses Michael Levi. He's also 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 also spent most of his time picking feuds with seemingly anyone who will listen, including Rick Ross, Kendrick Lamar and The Game. Though there have been rumored signings to new labels, t's uncertain whether Shyne will even release a proper third album.
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