|Actor/Actress :||Callum Keith Rennie|
Haley paid Roy to act as a guide for her, Ben and unofficially Sam and Dean Winchester on their hunt at Blackwater Ridge, Lost Creek for the missing Tommy and the creature responsible. They trekked through the woods to Tommy's camp, and found it in ruins and soon learned that the creature responsible was hunting them.
When Sam and Dean explained that the creature was a Wendigo and that they could protect themselves against it with Anasazi symbols, Roy was highly skeptical and the least serious about this. The next day, when the Wendigo attacked, Roy went after and shot at it, aggravating the creature and causing it to kill Roy by ambushing him and snapping his neck.
Roy viewed Dean as an inferior and less mature and experienced hunter and vice versa.
Roy was reluctant about Ben coming along on the hunt, as he felt that Ben would be unsafe.