Geoff Pierson Jack Malloy Actor, Director Bobcat Goldthwait Mr. Floppy Actor Stephanie Hodge Jennie Malloy Actor Kevin Connolly Ryan Malloy Actor, Director Nikki Cox Tiffany Malloy Actor Justin Berfield Ross Malloy Actor Joyce Van Patten Maureen Slattery Actor Allan Trautman Mr. Dunn Actor Oliver Muirhead Guest Star Jenna Von Oy Guest Star Don Novello Guest Star Michael Houston King Guest Star Richard Sanders Guest Star Kevin Ruff Guest Star Bridget Flanery Guest Star Dana Daurey Guest Star Jelene Daney Guest Star Wendy Benson-Landes Guest Star Linda Day Director Pat Maloney Director Howard Murray Director Andrew Susskind Director Wendy Neckels Director Mark O'Keefe Writer Harriette Regan Director Gerry Cohen Director J. Stewart Burns Writer Marcy Vosburgh Writer Christina Lynch Writer Arthur Silver Writer Kimberly Silver Writer Gabrielle Topping Writer