Ben Affleck as Buddy Amaral

Gwyneth Paltrow as Abby Janello

Natasha Henstridge as Mimi Prager

Tony Goldwyn as Greg Janello

Johnny Galecki as Seth

Joe Morton as Jim Willer

Alex D. Linz as Scott Janello

David Dorfman as Joey Janello

Jennifer Grey as Janice Guerrero

Caroline Aaron as Donna

Edward Edwards as Ron Wachter

Lisa Carpenter-Prewitt as Carol Wilson

Lisa Joyner as T.V. Announcer

Richard Saxton as CNN Reporter

Juan Garcia as Kevin Walters

Mary Ellen Lyon as Ellen Seitz

Thea Mann as Karen

Matthew Frauman as Luke

Sam Robards as Todd Exner

Ty Murphy as Josh

David McCharen as Infinity Air Commercial Narrator

Julianne Christie as Zola

Jeff Garlin as Emcee

Nicole Tocantins as Dionne

Ashley Montgomery as Prom Girl

Erik Audé as Prom Boy

Scott Alan Smith as Jack

Mark Ankeny as Tom

Julia Campbell as Sue

Michael Laskin as Frank Steadman

Michael Ayala as Court T.V. Reporter

David St. James as Judge

Don Amendolia as Infinity Attorney

John Levin as Janice's Attorney

Chris Harrison as Chicago Anchor

David Paymer as Prosecuting Attorney Mandel (uncredited)

Katherine Disque as Gate Attendant (uncredited)