Cast:

• Jason London Randall 'Pink' Floyd
• Rory Cochrane Ron Slater
• Wiley Wiggins Mitch Kramer
• Sasha Jenson Don Dawson
• Michelle Burke Jodi Kramer
• Adam Goldberg Mike Newhouse
• Anthony Rapp Tony Olson
• Matthew McConaughey David Wooderson
• Marissa Ribisi Cynthia Dunn
• Shawn Andrews Kevin Pickford
• Cole Hauser Benny O'Donnell
• Milla Jovovich Michelle Burroughs
• Joey Lauren Adams Simone Kerr
• Christin Hinojosa Sabrina Davis
• Ben Affleck Fred O'Bannion
• Jason O. Smith Melvin Spivey
• Deena Martin Shavonne Wright
• Parker Posey Darla Marks
• Nicky Katt Clint Bruno
• Catherine Avril Morris Julie Simms
• Christine Harnos Kaye Faulkner
• Esteban Powell Carl Burnett
• Mark Vandermeulen Tommy Houston
• Jeremy Fox John Hirschfelder
• Parker Brooks Kyle Eschenbrenner
• Terry Mross Coach Conrad
• Kim Krizan Ms. Ginny Stroud, high school teacher
• Julius Tennon Mr. Payne, junior high school teacher
• Richard Dillard Frank Pickford
• Kathleen Cunningham Mrs. Pickford, Kevin's Mom
• Katherine Asher Mrs. Burnett, Carl's Mom
• Zooey Greif Pentico
• Rick Moser Assistant Coach
• John Swasey Beer Deliver Guy
• Zach Taylor Freshman Smartass
• Jacob Jones Freshman Smartass
• Priscilla Kinser Freshman Girl 1
• Erika Geminder Freshman Girl 2
• Heidi Van Horne Freshman Girl 3
• Zeke Mills Old Timer
• Michael Gillespie Party Guy
• Tom Hoeck Chaparone
• Fred Lerner Guy with Pistol
• David Blackwell Liquor Store Clerk
• Autumn Barr Stacy
• Doug Taylor Cop
• Bob Moser Cop
• Mona Lee Fultz Mrs. Kramer, Mitch's Mother
• Mike Enright Guy at party
• James 'Kimo' Wills Guy at Party
• Jessica Wilson Senior Girl, Featured
• Renée Zellweger Girl in blue pickup truck