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