Michael Polish Director Mark Polish Henry McCarthy Actor, Screenwriter Winona Ryder Scarlet Smith Actor Sean Astin Big Girl Actor Josh Holloway Wino Actor Hilary Duff Shasta O'Neil Actor Marc Blucas Brad Nelson Actor Chevy Chase Principal Marshall Actor Frances Conroy Mrs. Leuchtenberger Actor Dee Wallace Mrs. McCarthy Actor Michael Gross Mr. McCarthy Actor Jessica St. Clair Darcy Portola Actor M. David Mullen Cinematographer Cary Gries Film Editing Helen Harwell Art Director Peggy Paola Set Decoration Christie Wittenborn Costume Design Janet DuBois Producer Ken Johnson Producer Jonathan Sheldon Producer Kelly Wagner Casting