Guest Stars Samantha Smith as Mary Winchester Jeffrey Dean Morgan as John Winchester Adrianne Palicki as Jessica Moore Sarah Shahi as Constance Welch Steve Railsback as Joseph Welch Ross Kohn as Troy Squire R.D. Call as Sheriff Pierce Co Starring Hunter Brochu as Young Dean Winchester Miriam Korn as Rachel Richard Dano as Hotel Clerk Jamil Walker Smith as Luis Derek Webster as Deputy Jaffe Robert Peters as Deputy Hein Elizabeth Bond as Amy Hein Cletus Young as Motel Clerk