Sarah Michelle Gellar as Cindy Bandolini

Adrian Grenier as Alan Jensen

Joey Lauren Adams as Chesney Cort

Eric Stoltz as Teddy Carter

Rebecca Gayheart as Kelly Morgan

John Neville as Dr. Reese

Gianni Russo as Andrew Bandolini

Michael Aparo as Russell

Scottie Epstein as Mario

Polly Shannon as Juliet

Phillip Jarrett as Coach Preston

Ray Allen as Marcus Blake

Clé Bennett as Hal

Landy Cannon as Butch

Al Franken as Al Franken

Thomasin Franken as Al Franken's Daughter

Joe Pingue as Joe

Booth Savage as Steve Jensen

Maria Ricossa as Charlotte Jensen

Adam Bloch as Kenner