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
Rob Gordon
Iben Hjejle
Laura
Todd Louiso
Dick
Jack Black
Barry Judd
Lisa Bonet
Marie DeSalle
Catherine Zeta-Jones
Charlie Nicholson
Joan Cusack
Liz
Tim Robbins
Ian Raymond
Chris Rehmann
Vince
Ben Carr
Justin
Lili Taylor
Sarah Kendrew
Joelle Carter
Penny Hardwick
Natasha Gregson Wagner
Caroline Fortis
Shannon Stillo
Alison Jr. High
Drake Bell
Rob Jr. High
Laura Whyte
Laura's Mom
Sara Gilbert
Anaugh Moss
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
Erik Gundersen
Marco
Bruce Springsteen
Alex Désert
Louis
Alan S. Johnson
Man In Store
Ian Belknap
Party Guest
Andrew Micheli
Polly Noonan
Philip Rayburn Smith
Michele Graff
Susie Cusack
Liam Hayes
Piano Player
Damian Rogers
Greenday Girl
Robert A. Villanueva
Skateboarder
Joe Spaulding
Flea Market Musician
Scott A. Martin
Bartender
Heather Norris
Laura's Friend
Timothy W. Tiedje
Operator (uncredited)
James Azrael
Glam Rocker (uncredited)
Ian Michaels
Guy in Chem Lab (uncredited)
Susan Hegarty
Laura's Mom (voice) (uncredited)
Thérèse DePrez
Production Design
Seamus McGarvey
Director of Photography
Victoria Thomas
Casting
Scott Rosenberg
Screenplay
Stephen Frears
Director
D.V. DeVincentis
Steve Pink
Rudd Simmons
Producer
Tim Bevan
David Chapman
Howard Shore
Original Music Composer
Mick Audsley
Editor
Jeffrey Wetzel
First Assistant Director
Aiman A. Humaideh
Second Assistant Director
Peter Joly
Supervising Sound Editor
Larry Lundy
Set Decoration
Michael Redfern
Foley Editor
Clare Mahoney
Foley Artist
Mike Newell
Executive Producer
Chiemi Karasawa
Script Supervisor
Jason Swanscott
Carl Fischer
Boom Operator
Chris Nolte
Stunt Double
Tarn Harper
Post Production Accountant
Gina Panno
Costumer
Property Master
Kim Taylor-Coleman
Casting Associate
Petur Hliddal
Sound Mixer
Joel Prihoda
Leadman
Danny Longhurst
Dialogue Editor
Liza Chasin
Kathy Nelson
Music Supervisor
Adrian Rhodes
Sound Re-Recording Mixer
Diane Greaves
Jeanne Van Phue
Key Makeup Artist
Derrick Kardos
Graphic Designer
Co-Producer
Nicholas Lundy
Art Direction
Jennifer Jobst
Costume Supervisor
Billy Higgins
Unit Production Manager
Joan Altman
Production Accountant
Phillip Ellman
On Set Dresser
Dialect Coach
Ted Swanscott
Foley Mixer
Demetra Diamantopoulos
Location Manager
Robert Swander
Best Boy Electric
Terry Isted
Michael Higham
Supervising Music Editor
Wendy Weidman
Melissa Moseley
Still Photographer
Joe Lisanti
Music Editor
Alan Greenspan
David Morenz
First Assistant Camera
Heather Pollock
Terry Baughman
Construction Coordinator
Rick LeFevour
Stunt Coordinator
Tania Blunden
Post Production Supervisor
Brendan Donnison
ADR Voice Casting
Shari Johanson
Art Bartels
Key Grip
John Stanborough
Color Timer
A. Welch Lambeth
Transportation Coordinator
Will Gatlin
Craft Service
Nick Hornby
Novel
Joan Philo
Extras Casting
Edward J. Reardon
Set Medic
Emma Thomas
Producer's Assistant
Robert Byrnes
Michael Cronin
Patricia Newby
Anne Johns
Production Coordinator
Anne Berger
Second Second Assistant Director
Anita Brongiel
Production Secretary
Deborah Evans
Payroll Accountant
Chad Erickson
Camera Intern
Margaret Morettini
Assistant Costume Designer
William R. Nielsen Jr.
Camera Operator
Thomas Coe
Margaret J. Orlando
Assistant Production Coordinator
Laura Connolly
Key Hair Stylist
Mark Rose
Assistant Sound Editor
Michael D. Gianneschi
Assistant Property Master
Mags Arnold
First Assistant Editor
Louise Spencer
Unit Publicist
Elizabeth Miller
Loader
Andy Wheeler
First Assistant Accountant
Daniel W. Fuller
Second Assistant Camera
Jeffrey A. Williams
Utility Sound
Kate Higham
James A. Miller
Gaffer
Laura Bauer
Costume Designer
Adrienne Swan
Second Assistant Accountant
Naomi Donne
Makeup & Hair
Claire Simon
Adam Graham
Location Assistant
Joanna S. Frank
Production Assistant
Ed Portoghese
Fernando M. Briones
Dolly Grip
Jennifer Baron
Assistant Location Manager
Sam Barkan
Special Effects Coordinator
Melissa Sadoff
John David Wolfe
Jon Schluenz
William T. Hogan III
Michael Lange
Best Boy Grip
Doug Dearth
Music Coordinator
Eric H. Heisner
David Malley
Adam Rosen
Dan Koretzky
Production Consultant
Juliette Dow
Anne Devereux
Kenneth w. Bradley
Jeff Sternberg
Gareth Jones
Score Engineer
Dawn Patch
Ed Rak
Veloz Gomez
Ronald Kane
Construction Foreman
Conductor
Music Arranger
Rick Norman
Sound
Ray Conchado
Special Effects
