Winokur won the 2003 Tony Award for Best Leading Actress in a Musical, Drama Desk Award, Theatre World Award, and Outer Critics Circle Award for her performance in Hairspray. She had previously appeared on Broadway as "Pink Lady Jan" in the revival of Grease.
Winokur has also played roles in films and on TV such as American Beauty, Never Been Kissed, Teaching Mrs. Tingle, Scary Movie, Beautiful Girl (for ABC Family), and Fever Pitch.