Jason London as Pink

Matthew McConaughey as Wooderson

Joey Lauren Adams as Simone

Rory Cochrane as Slater

Wiley Wiggins as Mitch

Adam Goldberg as Mike

Anthony Rapp as Tony

Sasha Jenson as Don

Shawn Andrews as Pickford

Milla Jovovich as Michelle

Ben Affleck as O'Bannion

Marissa Ribisi as Cynthia

Michelle Burke as Jodi

Deena Martin as Shavonne

Cole Hauser as Benny

Christine Harnos as Kaye

Mark Vandermeulen as Tommy

Esteban Powell as Carl

Jeremy Fox as Hirschfelder

Jason O. Smith as Melvin

Christin Hinojosa as Sabrina

Parker Posey as Darla

Catherine Morris as Julie

Nicky Katt as Clint

Parker Brooks as Stoner

Zach Taylor as Freshman Smartass

Jacob Jones as Freshman Smartass

Rick Moser as Assistant Coach

Terry Mross as Coach Conrad

Kim Krizan as Ms. Stroud

Zooey Greif as Pentico

Julius Tennon as Mr. Payne

Priscilla Kinser as Freshman Girl

Erika Geminder as Freshman Girl

Heidi Van Horne as Freshman Girl

Katherine Asher as Carl's Mom

Kathleen Cunningham as Pickford's Mom

Richard Dillard as Pickford's Dad

John Swasey as Beer Delivery Guy

Zeke Mills as Old Timer

Michael Gillespie as Party Guy

Tom Hoeck as Chaperone

Fred Lerner as Guy with Pistol

David Blackwell as Liquor Store Clerk

Autumn Barr as Stacy

Doug Taylor as Cop

Bob Moser as Cop

Mona Lee Fultz as Mitch's Mother

Chris M. Allport as Student (uncredited)

Rose Barrett as Pink's Sister (uncredited)

Tara Battani as Party Girl (uncredited)

Adam Boster as Booger (uncredited)

Josh Caldwell as Guy at Party (uncredited)

Nicole Emmons as Girl in Pool Hall (uncredited)

Mike Enright as Guy at Party (uncredited)

Chris Green as O'Bannion's Pool Partner (uncredited)

Karey Green as Senior Girl (uncredited)

KaiCarra as Girl in Bikini (uncredited)

Jessica Looney as Senior Girl (uncredited)

Renée Zellweger as Girl in Blue Truck (uncredited)

Anthony Pedone as Parking Lot Kid (uncredited)

Ted Perez as Guy at School / Guy at Party (uncredited)

Damian Tamburro as Student (uncredited)

Chris Western as Smoking Hippie (uncredited)

James 'Kimo' Wills as Guy at Party (uncredited)

Heath Young as Student (uncredited)