Wayne Kramer Director, Writer William H. Macy Bernie Lootz Actor Alec Baldwin Shelly Kaplow Actor Maria Bello Natalie Belisario Actor Shawn Hatosy Mikey Actor Ron Livingston Larry Sokolov Actor Paul Sorvino Buddy Stafford Actor Estella Warren Charlene Actor Arthur J. Nascarella Nicky "Fingers" Bonnatto Actor M.C. Gainey Highway Officer Actor Ellen Greene Doris Actor Joey Fatone Johnny Capella Actor Don Scribner Lou Actor Tony Longo Tony Actor Richard Israel Marty Goldfarb Actor Timothy Landfield The Player Actor T.J. Gioia Bulldog Actor Jewel Shepard Hooker Actor Gordon Michaels Mr. Pinkerton Actor Doc Watson Morrie Actor Frank Hannah Writer Michael A. Pierce Producer Sean Furst Producer Edward R. Pressman Executive Producer John Schmidt Executive Producer Alessandro Camon Executive Producer Brett Morrison Executive Producer Robert Gryphon Executive Producer James Whitaker Cinematographer Toby Corbett Production Design Kristin M. Burke Costume Design Arthur Coburn Film Editor Mark Isham Music