John Putch Director Bethany Joy Lenz Lucy Hardgrove Actor Kristoffer Polaha Jack Huston Actor Robert Picardo Harold Balaban Actor Mary Beth McDonough Director Actor A.K. Benninghofen Margaret Actor Annabelle Borke Ava Hayward Actor Colton Little Claude Lancaster Actor Jonathan Frakes Winston Actor David Alexander William West Actor Genevieve Padalecki Peggy Actor Jason Saucier Security Guard Actor Tommy Cresswell Michael Balaban Actor Alphie Hyorth Head Angel Actor Caity Brewer Becca Actor Wes Brown Charlie Actor Philena Gilmer Sandra Actor Ray Ficca Gus Actor Ray Fawley James's Father , 1947 Actor Actor Bobbie Peterson Tree Lighting Patron Actor Barbara Nuss Stiles Present Day Tourist Actor Zander Ash Young boy at Christmas party Actor Josh Yarusinsky Waiter Actor Marcy Holland Screenwriter Andrew Gernhard Producer Colin Theys Producer Dustin Rikert Executive Producer Andrew Rawson Cinematographer Tommy Fields Original Music Shane Meador Production Design Matt Parker Art Director Christi Whiteley Set Decoration Keith Nielsen Costume Design Tracy Kilpatrick Casting