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)