Jason London

Pink

Matthew McConaughey

Wooderson

Joey Lauren Adams

Simone

Rory Cochrane

Slater

Wiley Wiggins

Mitch

Adam Goldberg

Mike

Anthony Rapp

Tony

Sasha Jenson

Don

Shawn Andrews

Pickford

Milla Jovovich

Michelle

Ben Affleck

O'Bannion

Marissa Ribisi

Cynthia

Michelle Burke

Jodi

Deena Martin

Shavonne

Cole Hauser

Benny

Christine Harnos

Kaye

Mark Vandermeulen

Tommy

Esteban Powell

Carl

Jeremy Fox

Hirschfelder

Jason O. Smith

Melvin

Christin Hinojosa

Sabrina

Parker Posey

Darla

Catherine Morris

Julie

Nicky Katt

Clint

Parker Brooks

Stoner

Zach Taylor

Freshman Smartass

Jacob Jones

Freshman Smartass

Rick Moser

Assistant Coach

Terry Mross

Coach Conrad

Kim Krizan

Ms. Stroud

Zooey Greif

Pentico

Julius Tennon

Mr. Payne

Priscilla Kinser

Freshman Girl

Erika Geminder

Freshman Girl

Heidi Van Horne

Freshman Girl

Katherine Asher

Carl's Mom

Kathleen Cunningham

Pickford's Mom

Richard Dillard

Pickford's Dad

John Swasey

Beer Delivery Guy

Zeke Mills

Old Timer

Michael Gillespie

Party Guy

Tom Hoeck

Chaperone

Fred Lerner

Guy with Pistol

David Blackwell

Liquor Store Clerk

Autumn Barr

Stacy

Doug Taylor

Cop

Bob Moser

Cop

Mona Lee Fultz

Mitch's Mother

Chris M. Allport

Student (uncredited)

Rose Barrett

Pink's Sister (uncredited)

Tara Battani

Party Girl (uncredited)

Adam Boster

Booger (uncredited)

Josh Caldwell

Guy at Party (uncredited)

Nicole Emmons

Girl in Pool Hall (uncredited)

Mike Enright

Guy at Party (uncredited)

Chris Green

O'Bannion's Pool Partner (uncredited)

Karey Green

Senior Girl (uncredited)

KaiCarra

Girl in Bikini (uncredited)

Jessica Looney

Senior Girl (uncredited)

Renée Zellweger

Girl in Blue Truck (uncredited)

Anthony Pedone

Parking Lot Kid (uncredited)

Ted Perez

Guy at School / Guy at Party (uncredited)

Damian Tamburro

Student (uncredited)

Chris Western

Smoking Hippie (uncredited)

James 'Kimo' Wills

Guy at Party (uncredited)

Heath Young

Student (uncredited)