Guest Stars John Hoogenakker as Tall Man / Carl Wilkes Robin Weigert as Crysilda Wilkes Sarah Gadon as Rita K. Green Co Starring Georgia Lyman as Heather Ruby Cruz as Teen Annie Jennifer LaFleur as Mallory Madison Johnson as Young Annie Reese Grande as Emily Daniel McLaughlin as Diego Cheryl Singleton as Teacher AJ Jastrab as Brat #1