Discovered and produced by his first cousin DJ / Producer Howie Tee, Chubb Rock first appeared on the national scene with his 1988 self-titled debut Chubb Rock and 1989’s And the Winner is… The latter produced the minor hit “Ya Bad Chubbs” which garnered air play on Yo! MTV Raps during that time.

His 1990 release entitled The One reached No. 13 on Billboard’s Top Hip-Hop/R&B chart for that year. Three singles from that release, “Treat ‘Em Right”, “Just The Two of Us” and “The Chubbster”, made it to No. 1 on Billboard’s Top Rap Singles chart list for the same year.

The following year saw the release of I Gotta Get Mine, Yo, a release that featured guest performances from Grand Puba Maxwell and Poke. This release also helped fledgling music producers Trackmasters, on their rise to prominence, as the group handled production duties on the recording. Chubb Rock also made an appearance on MC Serch’s 1992 song “Back to the Grill.”

Chubb Rock was a member of the 1995 incarnation of the Crooklyn Dodgers, a hip hop act that also featured OC and Jeru the Damaja. His backup dancers started another group, A.T.E.E.M, which released its debut, A Hero Ain’t Nothin’ But A Sandwich, in 1992 on Select Records.

In 1996, he appeared on the Red Hot Organization’s compilation album America is Dying Slowly, alongside Wu-Tang Clan, Coolio, and Fat Joe, among others. The album, meant to raise awareness of the AIDS epidemic among African American men, was heralded as a masterpiece by The Source magazine.