Guest Stars Samantha Smith as Mary Winchester Keith Szarabajka as Professor Donatello Redfield Christian Keyes as Apocalypse World Michael Jeffrey Vincent Parise as Asmodeus Co Starring Alex Barima as Drexel Aubrey Arnason as Bartender Eric Breker as Alternate Universe Hunter Mark Sweatman as Tattooist Adil Zaidi as Drunk Demon Ryan S. Williams as Angel Commander Michelle Clarke-Brown as Female Demon