"After his long-time girlfriend dumps him, a thirty-year-old record store owner seeks to understand why he is unlucky in love while recounting his "top five breakups of all time"."
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
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
Polly Noonan
Philip Rayburn Smith
Michele Graff
Susie Cusack
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)
Stephen Frears
Director
D.V. DeVincentis
Screenplay
Steve Pink
Scott Rosenberg
Howard Shore
Original Music Composer
Tim Bevan
Producer
Rudd Simmons
Seamus McGarvey
Director of Photography
David Chapman
Production Design
Thérèse DePrez
Mick Audsley
Editor
Victoria Thomas
Casting
Mike Newell
Executive Producer
Alan Greenspan
Liza Chasin
Co-Producer
Kathy Nelson
Music Supervisor
Billy Higgins
Unit Production Manager
Jeffrey Wetzel
First Assistant Director
Aiman A. Humaideh
Second Assistant Director
Rick LeFevour
Stunt Coordinator
Chris Nolte
Stunt Double
Nicholas Lundy
Art Direction
Demetra Diamantopoulos
Location Manager
Joan Altman
Production Accountant
Petur Hliddal
Sound Mixer
Tania Blunden
Post Production Supervisor
Peter Joly
Supervising Sound Editor
Michael Higham
Supervising Music Editor
David Morenz
First Assistant Camera
Carl Fischer
Boom Operator
Tarn Harper
Post Production Accountant
Chiemi Karasawa
Script Supervisor
Jennifer Jobst
Costume Supervisor
Heather Pollock
Costumer
Gina Panno
Jeanne Van Phue
Key Makeup Artist
Larry Lundy
Set Decoration
Derrick Kardos
Graphic Designer
Joel Prihoda
Leadman
Phillip Ellman
On Set Dresser
Property Master
Danny Longhurst
Dialogue Editor
Michael Redfern
Foley Editor
Robert Swander
Best Boy Electric
Art Bartels
Key Grip
Kim Taylor-Coleman
Casting Associate
Wendy Weidman
Dialect Coach
Melissa Moseley
Still Photographer
Terry Baughman
Construction Coordinator
Adrian Rhodes
Sound Re-Recording Mixer
Brendan Donnison
ADR Voice Casting
Ted Swanscott
Foley Mixer
Terry Isted
Diane Greaves
Foley Artist
Jason Swanscott
Clare Mahoney
A. Welch Lambeth
Transportation Coordinator
Will Gatlin
Craft Service
Shari Johanson
Music Editor
Joe Lisanti
John Stanborough
Color Timer
Nick Hornby
Novel
Joan Philo
Extras Casting
Emma Thomas
Producer's Assistant
Edward J. Reardon
Set Medic
Michael Cronin
Robert Byrnes
Patricia Newby
Thomas Coe
Laura Bauer
Costume Designer
William R. Nielsen Jr.
Camera Operator
Anne Johns
Production Coordinator
Margaret J. Orlando
Assistant Production Coordinator
Anita Brongiel
Production Secretary
Anne Berger
Second Second Assistant Director
Deborah Evans
Payroll Accountant
Adrienne Swan
Second Assistant Accountant
Andy Wheeler
First Assistant Accountant
Jeffrey A. Williams
Utility Sound
Chad Erickson
Camera Intern
Elizabeth Miller
Loader
Daniel W. Fuller
Second Assistant Camera
Michael D. Gianneschi
Assistant Property Master
Mags Arnold
First Assistant Editor
Kate Higham
Margaret Morettini
Assistant Costume Designer
Laura Connolly
Key Hair Stylist
Naomi Donne
Makeup & Hair
Mark Rose
Assistant Sound Editor
James A. Miller
Gaffer
Michael Lange
Best Boy Grip
Fernando M. Briones
Dolly Grip
Sam Barkan
Special Effects Coordinator
Claire Simon
Louise Spencer
Unit Publicist
Dan Koretzky
Production Consultant
Jennifer Baron
Assistant Location Manager
John David Wolfe
Location Assistant
Adam Graham
Doug Dearth
Music Coordinator
Ed Rak
Score Engineer
Gareth Jones
Anne Devereux
Juliette Dow
Melissa Sadoff
William T. Hogan III
Kenneth w. Bradley
Production Assistant
Veloz Gomez
Eric H. Heisner
David Malley
Joanna S. Frank
Dawn Patch
Ed Portoghese
Jon Schluenz
Jeff Sternberg
Adam Rosen
Ronald Kane
Construction Foreman
Conductor
Music Arranger
Rick Norman
Sound
Ray Conchado
Special Effects