Guest Stars Ridge Canipe as Young Dean Winchester Colin Ford as Teenage Sam Winchester Spencer Garrett as Edward Carrigan Merrilyn Gann as Madge Carrigan Co Starring Jennifer Copping as Mrs. Caldwell Emily Holmes as Mrs. Walsh Victoria Bidewell as Molly Johnson Alex Bruhanski as Santa Village Santa Zak Ludwig as Stevie Connor Christopher Levins as Jimmy Caldwell Douglas Newell as Grandfather