In 1994 Wilson joined the cast of the sitcom "Sister, Sister" (then on ABC) in a recurring role that continued through the show's 1995 move to The WB, playing Terrence, the shopkeeper love interest of Jackee Harry's Lisa, and long-suffering employer of titular twins Tia and Tamara. He abandoned that part to undertake the regular starring role on the UPN sitcom "Goode Behavior" (1996-1998), as Franklin Goode, a straight-laced college dean and family man whose life is turned upside down when his father Willie (Sherman Hemsley), a colorful, scheming ex-con, is released from prison and moves in with him. Wilson's portrayal was skillfully charming, and lacked any overbearing sitcom histrionics. Following the series' cancellation, the actor kept busy with guest appearances on "Boy Meets World" (ABC), "The Parent 'Hood" (The WB) and "Diagnosis Murder" (CBS). In 1999, Wilson was back on television with a regular role on the "Moesha" spin-off "The Parkers" (UPN) as Professor Oglevee, a staff member at Santa Monica Junior College who catches the eye of Nikki Parker, an enthusiastic and driven adult student matriculating along with her teenaged daughter Kim (Countess Vaughn).

While best known for his prolific television work, Wilson has appeared frequently on stage, in productions of several plays including "Dreamgirls", "The Tempest", "To Kill a Mockingbird" and most notably, a starring turn as the titular baseball legend in "Most Valuable Player: The Jackie Robinson Story", a production that toured Washington, DC, Europe, Peru, and Canada following its California debut.