Principal Takes a Holiday is a 1998 romantic comedy television film that aired on ABC's The Wonderful World of Disney anthology series.

The film premiered on January 4, 1998 and stars Kevin Nealon, Zachery Ty Bryan and Jessica Steen.

John Scaduto (Zachery Ty Bryan), a troublesome high school senior makes a deal with his parents that he will not get into any more trouble until he graduates to receive a $10,000 gift from his grandma.

However, when his principal Frank Hockenberry (Kurt Fuller) is involved in an accident in a prank that he planned, he finds a homeless man named Franklin Fitz (Kevin Nealon), to act as the acting principal to keep his parents and every one else none the wiser.

While acting as principal, Franklin falls for Celia Shine (Jessica Steen), a fellow teacher.