Guest Stars Misha Collins as Castiel Genevieve Padalecki as Ruby Julie McNiven as Anna Milton Robert Wisdom as Uriel Mark Rolston as Alastair Gwynyth Walsh as Psychiatrist Co Starring Drew Nelson as Crossroad Demon Anthony Harrison as Captive Demon Shawn Hall as Pool Player Michelle Hewitt-Williams as Maid Anna Williams as Ruby #1 Samantha Page as Little Girl Dave Collette as Demon Orderly Glenn Ennis as Lilith's Demon #1 Mark Ferns as Lilith's Demon #2
