Guest Stars Jim Beaver as Bobby Singer Steven Williams as Rufus Turner James Patrick Stuart as Dick Roman Carrie Anne Fleming as Karen Singer Chelah Horsdal as Bobby's Mother Henri Lubatti as Reaper Edward Foy as Ed Singer Co Starring Nicolai Lawton-Guistra as Young Dean Winchester Mary Alison Raine as ER Nurse Carmel Amit as Lara Coggins Shaker Paleja as Insurance Representative Collin MacKechnie as Young Bobby Cam Cronin as Doctor 6