Guest Stars Jim Beaver as Bobby Singer Sonya Salomaa as Rachel Matthew John Armstrong as Elias Finch Sam Hennings as Samuel Colt Scott Hylands as Judge Tye Mortimer Dean Wray as Sheriff Co Starring April Telek as Darla Gordon Michael Woolvett as Deputy Jim Shield as Demon Cowboy Frank C. Turner as Elkins Stephen Bradley Jones as Demon Cowboy Howard Siegel as Old Man