Kennen Ivory Wayans at Zanies

Kennen earned writing credit on the star's raunchy live performance feature Eddie Murphy Raw (1987), Keenen's visibility rose. Partnering with actor/director Robert Townsend, he had his first film hit with Hollywood Shuffle (1987), a pointed satire highlighting the plight of the black actor in Hollywood. Done in hilariously stereotypical fashion, one great bit had detective Townsend battling a blaxploitation villain named Jerry Curl (Wayans). Following this came another similar 1970s blaxploitation parody, the even bigger hit I'm Gonna Git You Sucka (1988) in which Keenen had the starring role and made his directorial debut. He played the revenge-minded, but not particularly macho Jack Spade alongside such icons of 1970s blaxploitation cinema as Jim Brown, Isaac Hayes and Bernie Casey. The film also featured several members of his family.

The sketch-oriented, Emmy-winning variety series "In Living Color" (1990) was Keenen's creative baby and ultimate pièce de résistance. He also turned the show into a family act as well with Damon, Kim, Marlon and Shawn all appearing on the irreverent series that showcased the deviously scathing social humor Keenen was infamous for. As host of the show he graciously spotlighted the comedy ensemble more than himself. Not only did the show introduce the public to a number of terrific black comedians, it made superstars out of brother Damon, as well as Jamie Foxx and Jim Carrey, the latter being one of the show's few white regulars. Jennifer Lopez also got her start as one of the original hip-hop dancing, sexy "Fly Girls."