Special Guest Stars Joan Cusack as Sheila Jackson Guest Stars Emma Greenwell as Mandy Milkovich Zach McGowan as Jody Silverman Dennis Cockrum as Terry Milkovich Chloe Webb as Monica Gallagher Stephanie Fantauzzi as Estefania David Wells as Father Pete Diora Baird as Meg Thierre Di Castro as Marco Ellen Gerstein as Aunt Rande J.P. Hubbell as Sergeant Stryker Moshe Kasher as Ruben J.D. Goldblatt as GED Teacher Co Starring Bruno Amato as Dock Worker Jack Impellizzeri as Hissrich Carl McDowell as Ricky