John Cusack

Rob

Iben Hjejle

Laura

Todd Louiso

Dick

Jack Black

Barry

Lisa Bonet

Marie De Salle

Catherine Zeta-Jones

Charlie

Joan Cusack

Liz

Tim Robbins

Ian

Chris Rehmann

Vince

Ben Carr

Justin

Lili Taylor

Sarah

Joelle Carter

Penny

Natasha Gregson Wagner

Caroline

Shannon Stillo

Alison Jr. High

Drake Bell

Rob Jr. High

Laura Whyte

Laura's Mom

Sara Gilbert

Anaugh

Rich Talarico

Barry's Customer

Matthew O'Neill

Beta Band Customer

Brian Powell

Middle Aged Customer

Margaret Travolta

Rob's Mom

Jillian Peterson

Laura's Sister Jo

Dick Cusack

Minister

Susan Yoo

Girl - 19 year old

Chris Bauer

Paul

K.K. Dodds

Miranda

Marilyn Dodds Frank

Alison's Mom

Duke Doyle

Kevin Bannister

Aaron Himelstein

Boy In Park

Jonathan Herrington

Chris Thompson

Daniel Lee Smith

Rock Guy

Leah Gale

Mourner

David Darlow

Mourner

Erik Gundersen

Marco

Bruce Springsteen

Bruce Springsteen

Alex Désert

Louis

Alan S. Johnson

Man In Store

Ian Belknap

Party Guest

Andrew Micheli

Party Guest

Polly Noonan

Party Guest

Scott A. Martin

Bartender

Susan Hegarty

Laura's Mom (voice) (uncredited)