James Van Der Beek
as Sean Bateman

Shannyn Sossamon
as Lauren Hynde

Ian Somerhalder
as Paul Denton

Jessica Biel
as Lara

Kate Bosworth
as Kelly

Jay Baruchel
as Harry

Thomas Ian Nicholas
as Mitchell

Russell Sams
as Richard

Kip Pardue
as Victor

Joel Michaely
as Raymond

Clifton Collins Jr.
as Rupert

Clare Kramer
as Candice

Faye Dunaway
as Mrs. Denton

Swoosie Kurtz
as Mrs. Jared

Colin Bain
as Donald

Eric Szmanda
as NYU Film Student

Chase Hampton
as Townie

Curtis Andersen
as Guy Rolling Keg

Quincy Evans
as Dicky

Skyler Stone
as Quinlivan

Kavan Reece
as Handsome Dunce

Theresa Wayman
as Food Service Girl

Michael Ralph
as Guest

Noelle Evans
as Crack Whore

Fred Savage
as A Junkie Named Marc

Eric Stoltz
as Mr. Lawson

Anderson Goncalves
as Bertrand

Lucille M. Oliver
as Young Nurse

Paul Williams
as Duty Doctor

Drew Wood
as Jim from Dartmouth

Malcolm Galt
as Hacky Sack Guy

Cheyenne Wilbur
as Maitre D'

Ron Jeremy
as At the Player Piano

Holly Hollywood
as Undressed to Get Screwed

Amber Smith
as Undressed to Get Screwed

Alaina
as Undressed to Get Screwed

Trisha Uptown
as Undressed to Get Screwed

Hayley Keenan
as Claudia

Jesse Heiman
as Lucky Party Goer (uncredited)

Aurora Snow
as Masked Naked Girl at Party (uncredited)

Keren Woodward
as Self (uncredited)

C. Robert Cargill
as Bus Station Townie (uncredited)

Adam Robitel
as Dumb Guy from LA (uncredited)