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 DuShon Brown as Teresa Zoran Korach as Jenks Tray McVay as Gang Leader Julia Boyd as Angie Zago Holly Hannula as Reporter Kevin Dorian as Man on Bus Brendon Eggertsen as Teenager Darris Love as Gangster
