Special Guest Stars Joan Cusack as Sheila Jackson Guest Stars Dennis Cockrum as Terry Milkovich Stephanie Fantauzzi as Estefania Harry Hamlin as Lloyd "Ned" Lishman Bernardo de Paula as Beto J. Michael Trautmann as Iggy Milkovich Eric Edelstein as Bobby Mallison Cameron Richardson as Cheryl C.J. Berdahl as Kyle Justine Lupe as Blake Collins Melissa De Sousa as Tina Co Starring Michael Patrick McGill as Tommy Kerry O'Malley as Kate Julia Boyd as Angie Zago Zoran Korach as Jenks DuShon Brown as Teresa Brendon Eggertsen as Teenager Darris Love as Gangster Kevin Dorian as Man on Bus Holly Hannula as Reporter Tray McVay as Gang Leader
