Whitfield was born in Brooklyn, New York. He guest-starred in several episodes of Friends as Dr. Barry Farber, Rachel's orthodontist ex-fiancé whom Rachel left at the altar on their wedding day. He also appeared in Dharma & Greg; Murder, She Wrote; Diagnosis Murder and CSI: Crime Scene Investigation as well as Curb Your Enthusiasm. In the 1992 film My Cousin Vinny, Whitfield starred as Stan Rothenstein, opposite Ralph Macchio. He also appeared in an episode of The Suite Life of Zack & Cody.
As a voice actor, Whitfield voiced Phobos on W.I.T.C.H. and Donatello in the TMNT film.
He played Benjamin, a Marine friend of Eddie Birdlace, in Dogfight.