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 Elizabeth Weinstein as Crowley's Assistant James R. Baylis as Guardian Demon Max Teichman as Man in Hell Ellen MacNevin as Praying Woman Jennifer Huva as Woman in Hell Emile Bertrand as Homeless Man / Demon Doron Bell as Crossroads Demon