William Robert Carey Director, Screenwriter Alicia Silverstone Tammy Actor Billy Burke Cowboy Actor Amanda Michalka Vallie Sue Actor, Producer Michael Spears Tenkill Actor Chandler Massey Angelo Actor Amelia Rose Blaire Loretta Actor Jeannetta Arnette Jacqueline Windsor Actor Dennis Cockrum Mr. Sunday Actor Sydney Sweeney Annie Actor Sierra Fisk Principal Actor Darin Heames Old Ray Actor Elizabeth Bond Denise Actor Adam Cagley Boyd Actor Sean Gowrie Producer Jose Daniel Bort Producer Scott Dolezal Producer Bruce Garlick Executive Producer Gary Holliday Executive Producer Jay Howard Executive Producer Mat Rybicki Executive Producer Alex Lehmann Cinematographer Dennis Virkler Film Editing Rick Spalla Film Editing John Hunter Original Music Michael Barton Production Design Bethany Barton Set Decoration Cherlyn Lanning Costume Design Kerry Barden Casting