After leaving daytime television, Whitfield starred in the short-lived Fox sitcom The Crew during 1995–96 season. In 1997, he went to star alongside Kadeem Hardison in another short-lived sitcom, Between Brothers. He had dramatic turn in the 2000 UPN series Secret Agent Man, it also was cancelled after one season. From 2002 to 2003, he starred alongside Tamara Taylor in another short-lived sitcom, Hidden Hills on NBC. From 2001 to 2002, Whitfield had a recurring role on the UPN sitcom Girlfriends. He also has appeared on The Jamie Foxx Show, NYPD Blue, Strong Medicine, Ghost Whisperer, CSI: Miami, Cold Case, and Grey's Anatomy.