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 R.D. Call as Sheriff Pierce Ross Kohn as Troy Squire Co Starring Hunter Brochu as Young Dean Winchester Miriam Korn as Rachel Richard Dano as Hotel Clerk Derek Webster as Deputy Jaffe Jamil Walker Smith as Luis Elizabeth Bond as Amy Hein Robert Peters as Deputy Hein Cletus Young as Motel Clerk