A Pittsburgh, PA, native, Cundieff entered show business as a stand-up comic. Performing at Los Angeles' Comedy Act theater while attending USC, he began associating with several young comics (Townsend, Wayans and his brother Damon) who would become notable figures in black-oriented comedy. He also met his future screenwriting and producing partner Darin Scott while a student. Cundieff began acting with several bit parts in Townsend's "Hollywood Shuffle" (1987) and followed up with a supporting role in Lee's "School Daze" (1988). He also appeared on TV doing guest shots on "Benson" and "thirtysomething" and a did stint on the NBC soap "Days of Our Lives".
Moving behind the scenes, Cundieff co-scripted (with sitcom writer Daryl G Nickens) the successful if uninspired sequel "House Party 2" (1991) and directed three music videos for veteran rocker Neil Young. He made his feature directing debut with "Fear of a Black Hat", a sharply observed, if quickly dated, "rapumentary" of the hip-hop music community, inspired by "This is Spinal Tap", Rob Reiner's popular 1983 "rockumentary" spoof. Cundieff also scripted, wrote song parodies, and co-starred as rapper Ice Cold. A surprise success at the 1993 Sundance Film Festival, "Fear of a Black Hat" was mishandled by its distributor (ITC) who shelved the film for a year before giving it a limited release.
Lee offered to executive produce Cundieff and Scott's follow-up, "Tales From the Hood", a boldly cartoonish horror film with a social conscience. The pair co-scripted and Cundieff played a small role in one of the four stories in this low-budget film that proved quite profitable.
Between film projects, Cundieff served as a correspondent on Michael Moore's cultish, acclaimed but low-rated comedy newsmagazine, "TV Nation" (NBC, 1994; Fox, 1995). His most celebrated segment demonstrated that NYC cabbies would more readily pick up a casually dressed convicted felon than a well-dressed Emmy Award-winning black actor. By 1997, Cundieff had several film and TV projects in various stages of development as a writer, actor and/or producer. He also had a third feature under his belt, the romantic comedy "Sprung", again co-writing with Scott and serving double duty as director and actor.