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)

Beverly D'Angelo
as Woman Selling Records (DVD version) (uncredited)