Originally published for Vulture on April 19th, 2021.

“I work hard for everything I own, and I deserve this / The hardest thing right about now is staying alive, who’d’ve thought Diddy would part ways with Clive?” 

Black Rob, “Live From the Eastside” (unreleased)

When people think of the dawn of the Bad Boy era in hip-hop in the early to mid-’90s, the focal point is often centered on the Notorious B.I.G. — his meteoric rise and tragic end. Less commonly recognized is the fact that Black Rob, né Robert Ross of Spanish Harlem, was one of the earliest signees to Bad Boy Records — joining the camp, founded by Uptown Records alum and mogul-in-training Sean “Puffy” Combs, soon after Craig Mack’s arrival in 1994 — and helped lay the groundwork for some of the quintessential moments in the label’s legacy for years before his platinum-selling debut album, Life Story, was finally released for public consumption in 2000, resulting in his biggest hit, “Whoa!” A street soldier who might have looked out of place in the Shiny Suit Era of Bad Boy’s glossy music videos but stood strong among some of the era’s greatest artists from Biggie to Mase, Black Rob charted his own critically acclaimed path in a dominant space up until his death at 51 on Saturday, April 17.

Originally under the moniker Bacardi Rob, it was Rob’s ear to the bellicose rhythms that pervaded Harlem’s streets that brought the fellow raucous rapper from the Johnson Houses, G. Dep, into the Bad Boy Entertainment fold in 1998. The two collaborated repeatedly throughout their tenure on the label, most notably on the classic single and video “Let’s Get It.” But even prior to getting G. Dep signed, Rob was essential to establishing the label’s presence. It was mutual friend R.P. who connected Bacardi Rob with Combs, whom he impressed with his skill set; Rob allowed Combs to rename him Black Rob for the stage. He also gained the favor of longtime Bad Boy executive and current president, Harve Pierre, who would ultimately prove critical to Rob’s career trajectory at the label. He’d go on to give a scene-stealing performance on Mase’s 1997 debut, Harlem World, with “24 Hrs. to Live,” alongside DMX; his “I Dare You” collaboration with Pierre, then performing under the stage name Joe Hooker, made the soundtrack to the 1998 film Slam; his rapport with the LOX — Bad Boy’s rap trio of Jadakiss, Styles P, and Sheek Louch — on the 2000 album cut “Can I Live” showcased his ability to hold court with some of the New York area’s biggest heavyweights. Rob was prominently featured on the iconic cover of Puff’s 1997 debut album, No Way Out, with a standout track of his own, “I Love You Baby,” and had features on tracks with Bad Boy’s stable of R&B artists, from 112 to Total. Biggie anointed him on 1998’s “Victory”: “Black Rob joined the mob, it ain’t no replacin’ him.”