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".
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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)
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Thérèse DePrez Production Design
Seamus McGarvey Director of Photography
Victoria Thomas Casting
Scott Rosenberg Screenplay
Stephen Frears Director
D.V. DeVincentis Screenplay
Steve Pink Screenplay
Rudd Simmons Producer
Tim Bevan Producer
David Chapman Production Design
John Cusack Screenplay
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 Foley Artist
Carl Fischer Boom Operator
Chris Nolte Stunt Double
Tarn Harper Post Production Accountant
Gina Panno Costumer
Timothy W. Tiedje Property Master
Kim Taylor-Coleman Casting Associate
Petur Hliddal Sound Mixer
Joel Prihoda Leadman
Danny Longhurst Dialogue Editor
Liza Chasin Executive Producer
Kathy Nelson Music Supervisor
Adrian Rhodes Sound Re-Recording Mixer
Diane Greaves Foley Artist
Jeanne Van Phue Key Makeup Artist
Derrick Kardos Graphic Designer
John Cusack Co-Producer
Nicholas Lundy Art Direction
Jennifer Jobst Costume Supervisor
D.V. DeVincentis Co-Producer
Billy Higgins Unit Production Manager
Joan Altman Production Accountant
Phillip Ellman On Set Dresser
Susan Hegarty Dialect Coach
Ted Swanscott Foley Mixer
Steve Pink Co-Producer
Demetra Diamantopoulos Location Manager
Robert Swander Best Boy Electric
Terry Isted Foley Mixer
Michael Higham Supervising Music Editor
Wendy Weidman Casting Associate
Melissa Moseley Still Photographer
Joe Lisanti Music Editor
Alan Greenspan Executive Producer
David Morenz First Assistant Camera
Heather Pollock Costumer
Terry Baughman Construction Coordinator
Rick LeFevour Stunt Coordinator
Tania Blunden Post Production Supervisor
Brendan Donnison ADR Voice Casting
Shari Johanson Music Editor
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 Set Medic
Michael Cronin Set Medic
Patricia Newby Set Medic
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 Stunt Double
Margaret J. Orlando Assistant Production Coordinator