Guest Stars Martin Cummins as Tom Keller Alvin Sanders as Pop Tate Nathalie Boltt as Penelope Blossom Lochlyn Munro as Hal Cooper Peter Bryant as Principal Waldo Weatherbee Tiera Skovbye as Polly Cooper Trinity Likins as Jellybean Jones Zoé De Grand Maison as Evelyn Evernever Eli Goree as Mad Dog Brit Morgan as Penny Peabody Chad Michael Murray as Edgar Evernever Gina Gershon as Gladys Jones Jonathan Whitesell as Kurtz Reese Alexander as Myles McCoy Anna Van Hooft as Ms. Ronson Co Starring Marion Eisman as Doris Bell Alison Araya as Janet Weiss Julian Haig as Elio Todd Mann as Nico Brad Mann as Leo Sam Spear as Deputy Henderson Shaker Paleja as Dr. Patel Jay MacDougald as Nuckles Schrute Wolsey Brooks as Deputy