Guest Stars William Stanford Davis as Potato Pie Brooke Smith as Frances Simpson Octavius J. Johnson as Marvin Gaye Washington Sheryl Lee Ralph as Claudette Josh Pais as Stu Feldman Frank Whaley as Van Miller Paul Michael Glaser as Allan Kristin Minter as Liza Hendricks Diego Serrano as Teddy Co Starring Robert G. Brewer as Eddie David Dastmalchian as English Teacher Leah Bateman as Girl #1 Sarah Lilly as Dean of Admissions Ashley Jackson as Girl #2 Jonathan Emerson as Dean Christopher Goodman as Russ Michael Edwin as Boston Detective Sonny Valens as Cual Martinez Aviad Bernstein as Jamie Feldman Aubrey Wood as Naked Girl Coleton Ray Falke as Kid in Class Dennis Napolitano as Toupee Singer