Guest Stars David Grant Wright as Dr. Sterling Morton Judith Chapman as Mrs. Moncrief Melissa Rivers as Tegan Cook Blake Shields as tbd Michael Dempsey as Mr. Keeley Keram Malicki-Sánchez as Lyn Moncrief / Monk Vanessa Dorman as Kimberly Bradley Warden as Christopher Keeley Co Starring Duke Stroud as Mr. Jerry Murphy Samuel McCorvey as Principal Worthy Greg Woodhill as Chad Brooks Tim McKiernan as Janitor