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

Esteban Powell

Carl

Christin Hinojosa

Sabrina

Parker Posey

Darla

Nicky Katt

Clint

Kim Krizan

Ms. Stroud

Julius Tennon

Mr. Payne

Heidi Van Horne

Freshman Girl

Richard Dillard

Pickford's Dad

John Swasey

Beer Delivery Guy

Fred Lerner

Guy with Pistol

David Blackwell

Liquor Store Clerk

Mona Lee Fultz

Mitch's Mother

Renée Zellweger

Girl in Blue Truck (uncredited)

Anthony Pedone

Parking Lot Kid (uncredited)

James 'Kimo' Wills

Guy at Party (uncredited)