Owen Wilson Kyle Ed Helms Peter J.K. Simmons Ronald Hunt Katt Williams Hitchhiker Terry Bradshaw Terry Bradshaw Ving Rhames Rod Hamilton Christopher Walken Dr. Tinkler Glenn Close Helen Baxter Katie Aselton Sarah Retta Annie Harry Shearer Gene June Squibb Mrs. Hunt Ali Wong Ali Zachary Haven Ethan Mary Grill Katherine Jessica Gomes Kaylani Sarah Skeist Pretty Flight Attendant Debra Stipe Karen Bradshaw Robert Pralgo Ferrari Owner Donna DuPlantier ER Doctor Robert Walker Branchaud Officer #1 Andrew Wilson Hotel Desk Clerk Ryan Cartwright Liam Ryan Gaul Sean Taylor Treadwell Kelly Jack McGee Kevin O'Callaghan Jim France Father McManus Ivan Mallon Young Peter (uncredited) Annie Starke Young Helen (uncredited)