Jason London Randall 'Pink' Floyd Rory Cochrane Ron Slater Wiley Wiggins Mitch Kramer Sasha Jenson Don Dawson Michelle Burke Jodie Kramer Adam Goldberg Mike Newhouse Marissa Ribisi Cynthia Anthony Rapp Tony Milla Jovovich Michelle Burroughs Matthew McConaughey David Wooderson Ben Affleck Fred O'Bannion Joey Lauren Adams Simone Kerr Parker Posey Darla Marks Nicky Katt Clint Kim Krizan Ms. Stroud Shawn Andrews Pickford Cole Hauser Benny Christine Harnos Kaye Christin Hinojosa Sabrina Esteban Powell Carl Mona Lee Fultz Mrs. Kramer Heidi Van Horne Freshman Girl Renée Zellweger Girl in Blue Pickup Truck (uncredited)