Scott Marshall Director Jessica Simpson Katie Actor Luke Wilson Ben Actor Larry Miller Richard Connelly Actor Penelope Ann Miller Sandra Connelly Actor Andy Dick Frankie Actor Rachael Leigh Cook Haley Actor Drew Fuller Billy Actor Willie Nelson Pap Paw Actor Ritchie Montgomery Mr. Carruthers Actor Matthew Flanagan Screenwriter John Cohen Screenwriter David McHugh Screenwriter Justin Berfield Producer Joe Simpson Producer Lati Grobman Producer Freddy Braidy Producer Richard Salvatore Producer Jason Felts Producer David E. Ornston Producer Boaz Davidson Executive Producer Danny Dimbort Executive Producer Michael P. Flannigan Executive Producer Avi Lerner Executive Producer Mark Irwin Cinematographer Tara Timpone Film Editing Bob Ziembicki Production Design Richard Fojo Art Director Bradford Johnson Set Decoration Sara Markowitz Costume Design Brinkley A. Maginnis Casting