Jay Mohr Gary Actor Paula Marshall Allison Actor Jaime King Vanessa Actor Ryan Malgarini Tom Actor Kathryn Newton Louise Brooks Actor Al Madrigal Dennis Lopez Actor Ed Begley Jr. Dr. Walter Krandall Actor Kathleen Rose Perkins Joan Plummer Guest Star Cerina Vincent Miss St. James Guest Star Jon Fleming Diego Guest Star Ryan Hartwig Classmate Guest Star Ed Yeager Executive Producer Ric Swartzlander Executive Producer James Burrows Executive Producer, Director Barry Langer Writer