Max Minghella as Jerome

Sophia Myles as Audrey

John Malkovich as Professor Sandiford

Jim Broadbent as Jimmy

Matt Keeslar as Jonah

Ethan Suplee as Vince

Joel David Moore as Bardo

Nick Swardson as Matthew

Anjelica Huston as Art History Teacher

Adam Scott as Marvin Bushmiller

Jack Ong as Professor Okamura

Scoot McNairy as Army-Jacket

Jeremy Guskin as Eno

Monika Ramnath as Flower

Isaac Laskin as Kiss-Ass

Mike Stanley as Martel Drinker

Brian Turk as Cliffy

Jeanette Brox as Shilo

Finneus Egan as Vegan

Shelly Cole as Filthy-Haired Girl

Jean St. James as Mom

Cristen Coppen as Preppy Girl

Michael Shamus Wiles as Donald Baumgarten

Kate Moennig as Candace

Ezra Buzzington as Leslie

Lauren Lee Smith as Beat Girl

Travis Walck as Richard Natwick

Paul Collins as Professor David Zipkin

Marshall Bell as Lonny

Chris L. McKenna as Mikey

Marc Vann as Kevin

Roxanne Day as Jonah's Wife - Marie

Roxanne Hart as Mom Platz

Osman Soykut as Dad Platz

Katija Pevec as Cynthia Platz

Edith Jefferson as Doddering Aunt

Michael Lerner as Art Dealer

Jeff LeBeau as Lawyer

Richard Bakalyan as Cranky Guard

Kimi Reichenberg as Suburban Girl

John Bliss as Vince's Grandpa

Charlie Talbert as Vince's Editor

Amy Gross as Vince's Editor's Girlfriend

Alexandra Ryan as Nympho Slut

Bob Golub as Hector

Lauren Bowles as Woman Strangled

Zachary Maurer as Young Jerome

Brendan Walsh as Eugene

Brian Geraghty as Stoob

Valyn Hall as Cute Girl

Oliver Ryan Anderson as Cute Girl's Boyfriend

Curtis Taylor as Coach

Jesse Flanagan as Hurst

Dawn-Lyen Gardner as Coed

Laura Roth as Coed

Alexi Wasser as Female Student

Nathaniel Lee Jr. as Kid

Stacey Travis as Teacher

Wendy Haines as Grenadine Woman

Erik Walker as Punching Bully

Andre Marcus as Other Bully

Choice Skinner as Cop

Bob Jennings as Cop

Sam Sabbah as Scary Local

Lily Asinovsky as Girl Who Steps on Glass

Steve Buscemi as Broadway Bob D'Annunzio (uncredited)

Kristin Quick as Girl Student