Witt was introduced to a larger audience in the role of Cybill Shepherd's daughter, Zoey Woodbine, in the sitcom "Cybill". While playing that part, from 1995 to 1998, she also had film roles in Stephen Herek's "Mr. Holland's Opus", Alexander Payne's "Citizen Ruth", Robert Allan Ackerman's "Passion's Way" (based on the Edith Wharton novel, "The Reef"), and Richard Sears' comedy "Bongwater". After "Cybill" was cancelled, Witt went on to leading roles in Jamie Blanks' horror film "Urban Legend" (alongside Jared Leto, Joshua Jackson, and Rebecca Gayheart), and in Kevin Altieri/Touchstone Pictures' limited-release animated feature, "Gen¹³". In 2000, Witt had starring roles on episodes of the television shows "Ally McBeal" and "The Sopranos", the lead role in the Matthew Huffman comedy "Playing Mona Lisa" (featuring Harvey Fierstein, Elliott Gould, and Marlo Thomas), and a part in John Waters' "Cecil B. Demented".