Gregory's career has grown steadily from his beginnings in local theater, skit-comedy, television and commercials. He began his television career with recurring and guest starring roles in series such as Murder She Wrote, Lois and Clark: The New Adventures of Superman, Pacific Blue and Prey. He also appeared in a variety of comedy series such as Girlfriends, 3rd Rock from the Sun, Moesha, Hangin' with Mr. Cooper, Living Single, Moesha and The WB's The Steve Harvey Show. Before joining the cast of Charmed, Gregory co-starred as the parapsychologist Diamont Teague on the syndicated nighttime drama Baywatch Nights.

Gregory's feature film work includes Deliver Us from Eva, starring opposite L.L. Cool J and Gabrielle Union, Just Write with Jeremy Piven, and The Apocalypse, with Sandra Bernhard. He also appeared in the Disney made-for-television movie, The Barefoot Executive. He can next be seen in the up-coming feature film Getting Played, starring opposite Vivica A. Fox, Carmen Electra and Bill Bellamy.