John Cusack as Rob Gordon

Iben Hjejle as Laura

Todd Louiso as Dick

Jack Black as Barry Judd

Lisa Bonet as Marie DeSalle

Catherine Zeta-Jones as Charlie Nicholson

Joan Cusack as Liz

Tim Robbins as Ian Raymond

Chris Rehmann as Vince

Ben Carr as Justin

Lili Taylor as Sarah Kendrew

Joelle Carter as Penny Hardwick

Natasha Gregson Wagner as Caroline Fortis

Shannon Stillo as Alison Jr. High

Drake Bell as Rob Jr. High

Laura Whyte as Laura's Mom

Sara Gilbert as Anaugh Moss

Rich Talarico as Barry's Customer

Matthew O'Neill as Beta Band Customer

Brian Powell as Middle Aged Customer

Margaret Travolta as Rob's Mom

Jillian Peterson as Laura's Sister Jo

Dick Cusack as Minister

Susan Yoo as Girl - 19 year old

Chris Bauer as Paul

K.K. Dodds as Miranda

Marilyn Dodds Frank as Alison's Mom

Duke Doyle as Kevin Bannister

Aaron Himelstein as Boy In Park

Jonathan Herrington as Chris Thompson

Daniel Lee Smith as Rock Guy

Leah Gale as Mourner

David Darlow as Mourner

Erik Gundersen as Marco

Bruce Springsteen as Bruce Springsteen

Alex Désert as Louis

Alan S. Johnson as Man In Store

Ian Belknap as Party Guest

Andrew Micheli as Party Guest

Polly Noonan as Party Guest

Philip Rayburn Smith as Party Guest

Michele Graff as Party Guest

Susie Cusack as Party Guest

Liam Hayes as Piano Player

Damian Rogers as Greenday Girl

Robert A. Villanueva as Skateboarder

Joe Spaulding as Flea Market Musician

Scott A. Martin as Bartender

Heather Norris as Laura's Friend

Timothy W. Tiedje as Operator (uncredited)

James Azrael as Glam Rocker (uncredited)

Ian Michaels as Guy in Chem Lab (uncredited)

Susan Hegarty as Laura's Mom (voice) (uncredited)