James Toback
Director
Adrian Grenier
Alan Jensen
Sarah Michelle Gellar
Cindy Bandolini
Joey Lauren Adams
Chesney Cort
Eric Stoltz
Teddy Carter
Rebecca Gayheart
Kelly Morgan
Gianni Russo
Andrew Bandolini
Ray Allen
Marcus Blake
Mike Vetere
Russell
Scottie Epstein
Mario
John Neville
Dr. Reese
Polly Shannon
Juliet
Phillip Jarrett
Coach Preston
Adam Bloch
Kenner
Lauren Collis
Connie
Landy Cannon
Butch
Clé Bennett
Hal
Chantal Cousineau
Sandy
Maria Ricossa
Charlotte Jensen
Booth Savage
Steve Jensen
Mung-Ling Tsui
Reporter
Brendan Ryder
Jonathan
Kelly Ryder
Jonathan's Mother
Kristi Angus
Bartender
Tara Samuel
Waitress
Ayanna Sealey
Coed #1
Jamie Holmes
Coed #2
Al Franken
Himself
Thomasin Franken
Herself
Peter Mensah
Cyril the Butler
Joe Pingue
Joe
J. Miles Dale
Howie
Nick Bacon
Seth
Kate Crowley
Kate
Kimberly Pullis
Kimberly
Brian Schulz
Harvard Radio Broadcaster
Chris Wolfe
Harvard Radio Broadcaster
Lyssa J. Caster
Girl in Stands
Rick Ducommun
Police Officer Martino
David Lauren
Man with Coffee
Nicholas Marino
Boy in Street
Manajhjanihe Royalle
College Student
Michael Sercerchi
Basketball Player
Emily VanSonnenberg
Girl in Park
Kasia Vassos
Girl at Bar