Loser

Jason Biggs

Paul Tannek

Mena Suvari

Dora Diamond

Zak Orth

Adam

Thomas Sadoski

Chris

Jimmi Simpson

Noah

Greg Kinnear

Prof. Edward Alcott

Dan Aykroyd

Dad

Twink Caplan

Gena

Bobby Slayton

Sal

Robert Miano

Victor

Mollie Heckerling

Annie

Colleen Camp

Homeless Woman

Andy Dick

Another City Worker

Steven Wright

Panty Hose Customer

Brian Backer

Doctor

Meredith Scott Lynn

Dog Loving Girl

Stuart Cornfeld

Foreman

Taylor Negron

Photographer

Andrea Martin

Professor

Scott Thomson

Cell Phone Guy

Kedar Brown

Jay

Catherine Black

Military Jacket Girl

Rick Demas

Bouncer

Sanjay Talwar

Convenience Cashier

Tracy Dawson

Drug Saleswoman

Carolyn Goff

Kristen

Mike Beaver

Boy at Concert

Richard Blackburn

Security Guard

Billy Otis

Prisoner

Jenny Kim

Student Worker

Alison Sealy-Smith

University Official

Martin Roach

Veterinarian

Heidi Weeks

Saks Saleswoman

Daniela Olivieri

Store Tailor

Kavita Persaud

Hi Ro Student

Corwin Hall

Hi Ro Student

Andrew Storms

Hi Ro Student

Serena Lee

Hi Ro Student

Nick Bacon

Beer Store Clerk

Valerie Boyle

Aunt

Colleen Reynolds

Aunt

Jack Jessop

Grandfather

Mallory Margel

Paul's Sister

Patrick Mark

Bloody Nose Guy

Tanja Jacobs

Party Goer

Darrin Brown

Party Goer

James Barrett

Guy

Rob Tinkler

Bar Patron

Katherine Giaquinto

College Girl

Robinne Fanfair

College Girl

Clare Preuss

College Girl

Sadie LeBlanc

College Girl

Silvana Kane

College Girl

Kerri Michalica

College Girl

Geoffrey Antoine

Coffee Counter Guy

Danny Truelove

Dancing Kid

Marc McMulkin

Dancing Kid

Jonathon Fernandes

Dancing Kid

Tiffany Leonardo

Dancing Kid

David Spade

Video Store Clerk (uncredited)

Alan Cumming

Alan Cumming / Emcee (uncredited)