Special Guest Stars Joan Cusack as Sheila Jackson Guest Stars Noel Fisher as Mickey Milkovich Jane Levy as Mandy Milkovich Tyler Jacob Moore as Tony Markovich Chloe Webb as Monica Gallagher Joel Murray as Eddie Jackson Carlease Burke as Roberta Mo Gaffney as Christine Dowling Jerry Lambert as Randy Kulovitz Co Starring Michael Patrick McGill as Tommy Caitlin Kimball as Technician Alexis Rutter as Patty Kendra McCulty as Elaine Michael Krawic as Elaine's Dad Saachiko as Korean Lady Jeorge Bennett Watson as Mr. Tubbard Guy Massey as Jasper