Greg Coolidge Director, Writer Dane Cook Zack Actor Jessica Simpson Amy Actor Dax Shepard Vince Actor Andy Dick Lon Actor Tim Bagley Glen Gary Actor Brian George Iqbal Actor Efren Ramirez Jorge Actor Marcello Thedford Semi Actor Danny Woodburn Glen Ross Actor Harland Williams Russell Actor Sean Whalen Dirk Actor Shirly Brener Attractive Woman (Eyeglasses) Actor Barbara Dodd Granny Actor Alison Raimondi Sandy the Waitress Actor Z. Ray Wakeman Cameron Actor Don Calame Screenwriter Chris Conroy Screenwriter Joe Simpson Producer Barry Katz Producer Brian Volk-Weiss Producer Andrew Panay Producer Michael Paseornek Executive Producer John Sacchi Executive Producer Michael Burns Executive Producer Anthony B. Richmond Cinematographer Kimberly Ray Film Editing John Swihart Original Music Jon Gary Steele Production Design Guy Barnes Art Director David Eckert Art Director Rosario Provenza Art Director Traci Kirshbaum Set Decoration Denise Wingate Costume Design Rebecca Mangieri Casting Wendy Weidman Casting Barbara Fiorentino Casting