Emile Hirsch as Matthew Kidman

Elisha Cuthbert as Danielle

Timothy Olyphant as Kelly

Christopher Rodriguez Marquette as Eli

Paul Dano as Klitz

James Remar as Hugo Posh

Timothy Bottoms as Mr. Kidman

Donna Bullock as Mrs. Kidman

Jacob Young as Hunter

Brian Kolodziej as Derek

Amanda Swisten as April

Sung-Hi Lee as Ferrari

Ulysses Lee as Samnang

Harris Laskawy as Dr. Salinger

Julie Osburn as Jeannie

Laird Stuart as Mr. Ruether

Dane Garretson as Ryan Wenger

Richard Fancy as Mr. Peterson

Catherine McGoohan as Mrs. Peterson

Josh Henderson as Pep Rally Jock

Olivia Wilde as Kellie

Michael Villani as TV Talk Show Host

Autumn Reeser as Jane

Nicholas Downs as Bob in 70's Sex-Ed Film

Katie Stuart as Jennie

Matthew Wiese as Mule

John-Clay Scott as Rent-A-Cop

Maria Arcé as Chloe

Alonzo Bodden as Steel

Ellis Williams as Scholarship President

Stephanie Fabian as Mina Lopez

Dan Klass as School Photographer

Danny Seckel as Bob’s Friend in 70’s Sex-Ed Film

Reda Beebe as Cocktail Waitress

Brandon Irons as Troy

Bill Duggan as Guy All Over (uncredited)