Special Guest Stars Jim Beaver as Bobby Singer Guest Stars Mark Sheppard as Crowley Osric Chau as Kevin Tran Amanda Tapping as Naomi Ty Olsson as Benny Lafitte Assaf Cohen as Ajay Co Starring Gregory Taven as Vampire James R. Baylis as Guardian Demon Doron Bell as Crossroads Demon Ellen MacNevin as Praying Woman Jennifer Huva as Woman in Hell Emile Bertrand as Homeless Man / Demon Max Teichman as Man in Hell Elizabeth Weinstein as Crowley's Assistant