The Rules of Attraction

James Van Der Beek Sean Bateman Shannyn Sossamon Lauren Hynde Ian Somerhalder Paul Denton Jessica Biel Lara Kate Bosworth Kelly Jay Baruchel Harry Thomas Ian Nicholas Mitchell Russell Sams Richard Kip Pardue Victor Joel Michaely Raymond Clifton Collins Jr. Rupert Clare Kramer Candice Faye Dunaway Mrs. Denton Swoosie Kurtz Mrs. Jared Colin Bain Donald Eric Szmanda NYU Film Student Chase Hampton Townie Curtis Andersen Guy Rolling Keg Quincy Evans Dicky Skyler Stone Quinlivan Kavan Reece Handsome Dunce Theresa Wayman Food Service Girl Michael Ralph Guest Noelle Evans Crack Whore Fred Savage A Junkie Named Marc Eric Stoltz Mr. Lawson Anderson Goncalves Bertrand Lucille M. Oliver Young Nurse Paul Williams Duty Doctor Drew Wood Jim from Dartmouth Malcolm Galt Hacky Sack Guy Cheyenne Wilbur Maitre D' Ron Jeremy At the Player Piano Holly Hollywood Undressed to Get Screwed Amber Smith Undressed to Get Screwed Alaina Undressed to Get Screwed Trisha Uptown Undressed to Get Screwed Hayley Keenan Claudia Jesse Heiman Lucky Party Goer (uncredited) Aurora Snow Masked Naked Girl at Party (uncredited) Keren Woodward Self (uncredited) C. Robert Cargill Bus Station Townie (uncredited) Adam Robitel Dumb Guy from LA (uncredited)