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Guest cast, played by Robert Wisdom
- Episode 4x07: It's the Great Pumpkin, Sam Winchester (Oct 30, 2008)
- Episode 4x09: I Know What You Did Last Summer (Nov 13, 2008)
- Episode 4x10: Heaven and Hell (Nov 20, 2008)
- Episode 4x16: On the Head of a Pin (Mar 19, 2009)
Guest cast, played by Matt Ward
- Episode 5x13: The Song Remains the Same (Feb 4, 2010)