Special Guest Stars Joan Cusack as Sheila Jackson Guest Stars Noel Fisher as Mickey Milkovich Zach McGowan as Jody Silverman Chloe Webb as Monica Gallagher Stephanie Fantauzzi as Estefania J. Michael Trautmann as Iggy Milkovich Ed Lauter as Dick Healey Diora Baird as Meg Louise Fletcher as Peg Gallagher Joe Adler as Milkovich Brother Larry Clarke as Timothy Del Hunter-White as School Administrator Susan Krebs as Catholic Adoption Lady Co Starring Michael Patrick McGill as Tommy Nayo Wallace as Stacy William C. Mitchell as Teacher Mike Muscat as Barry