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Born in Kingston, Jamaica and bred in the New York City borough of Brooklyn, Chubb Rock — known for his authoritative and nimble flow, as well as an imposing frame — was a key rap artist of the late '80s and early '90s. He attended Brown University but abandoned his pre-med studies in favor of a music career. Supported by DJ and producer Howie Tee, his first cousin, he signed to the Select label — home of U.T.F.O. and Whistle, among others — and released his first album, Chubb Rock Featuring Hitman Howie Tee, in 1988. A remix of the album's "Caught Up," issued on 12", didn't chart but made a significant impact. The following year's And the Winner Is..., also made with Howie Tee, reached the Top 30 of Billboard's R&B Albums chart, highlighted by "Ya Bad Chubbs," which hit number 15 on the publication's Rap Singles chart and was regularly aired on Yo! MTV Raps.
During the early '90s, Chubb Rock released another pair of albums for Select: The One (1991) and I Gotta Get Mine Yo! (1992). The former spawned his biggest hit, the number one rap single "Treat 'Em Right" — another MTV staple. During the rest of the decade, he wasn't as active, though he was part of Crooklyn Dodgers '95, along with Jeru the Damaja and O.C., who contributed the DJ Premier-produced "Return of the Crooklyn Dodgers" to the Clockers soundtrack. He appeared beside Biz Markie and Prince Paul the following year on America Is Dying Slowly, a compilation for the Red Hot Organization. A fifth album, The Mind — his last release for Select — was released in 1997. After that, he recorded sporadically. Among his output during the following decades was a contribution to Prince Paul's Politics of the Business (2003), the album Bridging the Gap (2009), and a guest verse on Eric Roberson's "Summertime Anthem" (2011).