Tommy Davidson started his career as a stand-up comedian in 1986,[1] when a childhood friend convinced him to perform stand-up at The Penthouse strip club in Park View, Washington, D.C..[4][8] He continued performing in various comedy clubs throughout the Washington Metropolitan region, Baltimore, and Philadelphia. He opened concerts for Patti LaBelle,Starpoint, and Kenny G.[9] He performed on a fundraising telethon for WHMM in 1987.[10]

Davidson won an amateur stand-up competition at the Apollo Theater in 1987.[4] Soon afterwards, he moved to North Hollywood, California, where he met Martin Lawrence, who lived in his building.[4][11] He performed at the Comedy Store, where Robert Townsend heard of him and asked him to be the warm-up comic for an HBO special.[4] After performing atLuther Vandross and Anita Baker shows, he appeared on the Arsenio Hall Show.[4]

Davidson's first major exposure came on the variety show In Living Color, where he played various characters, including his impersonations of Sammy Davis, Jr. and Sugar Ray Leonard, and child victim of Homey D. Clown.