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 Dennis Boutsikaris as Professor Hearst David Wells as Father Pete Nicky Korba as Little Hank Carlease Burke as Roberta Candace Brown as Alana Murphy Micah Cohen as Jeff Murphy Desean Terry as Ron Co Starring Brandon Sims as Liam Gallagher Kerry O'Malley as Kate Alex Alexander as Stella Ronald William Lawrence as Gus Will Zahrn as Homeless Man