Ray McAnn is a son of Jim McAnn, one of the founders of the Midwestern Brewery Company, makers of Thighslapper Premium Ale.
Ray McAnn was camping in the woods with his brother and friends on the day his brother Trevor died. One of teens is telling a ghost story about Jenny Greentree.
He shows them the initials that the woman carved into a tree just before she died, and talks about how Jenny froze beneath the tree. Since then, her evil spirit haunts the woods. A bottle breaks and their drunk friend, Trevor McAnn, comes out of the woods, laughing.
Ray complains and Trevor invites him to call their father, Jim. However, Trevor suddenly hears something that no one else can, and then sees something come out of the woods. He runs away and they wonder what he's seen, and then hear Trevor scream. Ray goes after him and finds him lying dead in the woods, his stomach torn out.
Ray is drinking in his car when Chloe calls to tell him he should be with his family. He cuts her off and goes out into the woods looking for Trevor's killer, and spots a woman in a white dress. Ray runs after her but sees nothing, and then something grabs him, lifts him into the air, and rips him open.
It is revealed that he and his siblings Lillian and Trevor were killed by a Shōjō let loose by Dale Lampert as part of his plan to get revenge on Jim and Randy Baxter for selling the Brewery to large distributor, overriding Dale's wishes. His death and his siblings' deaths are later avenged by Dean Winchester when he kills the Shōjō with a katana.