During this time, Witt supported herself by playing piano at the Regent Beverly Wilshire Hotel. She went on to play small parts in Mike Figgis' Liebestraum (in which her brother Ian also appears), the Gen-X drama Bodies, Rest & Motion and the TV movie The Disappearance of Vonnie. In 1994, the red-haired Witt landed her first lead role in a film, playing a disturbed teenager in Fun. She received the Special Jury Recognition Award at the Sundance Festival and was nominated for Best Actress at the Independent Spirit Awards. This performance inspired Madonna to recommend Witt to be cast as her lover in the first segment, "The Missing Ingredient" of Four Rooms.

Witt was introduced to a larger audience playing the role of Zoey Woodbine, daughter of actress Cybill Shepherd's character in the sitcom Cybill from 1995 to 1998. Between seasons she starred in films: Mr. Holland's Opus, Alexander Payne's abortion comedy Citizen Ruth, Passion's Way and Bongwater. After Cybill was cancel