Matthew Lillard as Roger Sperling

Brett Davern as Alex Sperling

Rachelle Lefevre as Laura

Jennifer Walcott as Caitlin Stenson

Simona Fusco as Hedda

Rhoda Griffis as Nancy Sperling

Darla Haun as Mrs. Ashmore

Tom Arnold as Tom Arnold

Efren Ramirez as Hector

John Billingsley as Prof. James Kellogg

Jay Thomas as Martin 'Marty' Sperling

Sheena Lee as Lin

George Takei as Maitre D (Joon)

A.J. Alexander as The D.J.

Astrid Coppens as Bachelorette Party Guest (uncredited)

Janine Habeck as Clarissa

Monica Leigh as Trish

Heather Marie Marsden as Bree

Patricia De Leon as Julia

Peter Gabb as Mr. Burger

Robin Thomas as Mr. Stenson

Robert Davi as Robert Davi

Rachel Rogers as Bethany

Joe Reegan as Eddie

George Back as Jimmy Black

Pat Skipper as Frank

Andy Golden as Doug

Edith Dupré LeBlanc as Doug's Mom

Michael P. Cahill as Principal

Hunter Womack as Foreman

Michael Boatman as Donovan Tucker

Michael Arata as Doug's Dad

Stephanie Honoré as Victoria Mills

Ron Gural as Doug's Grandpa

Armando Leduc as Harvard Guy

Dane Rhodes as FBI Agent

Christie Hsiao as Sam

Jordana Woodland as Elle

Justin Ware as Random Guy

Arcadiy Golubovich as Unicorn

Tony Bentley as Senator Brewster

Maureen Phelan as Senator's Assistant

Tricia Vansant as Escort #1

James Barnett as Client

Wilfurt Hildabrandt as Harvard Alumni

Victoria Patenaude as Harvard Alumni

Louis St. Romain as Pool Boy

Claudia Stedelin as Senator Brewster's Secretary

John J. Anderson as Colleague (uncredited)

Dewayne Bateman as Client (uncredited)

Christine Biancardi as High Class Escort (uncredited)

Kelly Bird as Lola / Rich Dyke (uncredited)

Sean M. Blanchard as Bar Mitzvah Guest (uncredited)

David E. Brown as Harvard Alumni (uncredited)

Edward D. Caiado as Harvard Alumni (uncredited)

Michael Capp as Cab Driver (uncredited)

John Ceallach as Client (uncredited)

Danny Cosmo as Gimp (uncredited)

Michael Dardant as Frat Boy (uncredited)

Erica Day as Bachelorette (uncredited)

Ben Decker as Frat Boy (uncredited)

Mike Franklin as Client (uncredited)

Geraldine Glenn as Harvard U Parent (uncredited)

Russell M. Haeuser as Graduation Attendee (uncredited)

Jordan Johnson as Frat Boy (uncredited)

Jennifer Kelsey as Bachelorette Party Guest (uncredited)

Mikey King as Client (uncredited)

Scott M. King as Client (uncredited)

Cynthia LeBlanc as Harvard U. Parent (uncredited)

Elton LeBlanc as Brothel Client (uncredited)

Don Lincoln as Harvard Alumni (uncredited)

Mary Ly as Customer (uncredited)

Ann Mahoney as Marlene (uncredited)

Sami Naveed as Harvard Guy (uncredited)

Jay Oliver as Harvard Alumni (uncredited)

Larry Seal as Harvard Alumni (uncredited)

Deborah Garcia Smith as Harvard Alumni (uncredited)

M. Jearl Vinot as Client (uncredited)

Jaymon Yates as Client / Pool Guy with Gator (uncredited)