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)
Stephen Frears
Director
Tim Bevan
Producer
Rudd Simmons
Jun 5, 1975
Apr 21, 1993
Nov 26, 1987
Jun 14, 2002
Dec 17, 2004
Mar 1, 2002
Jan 1, 2003
Oct 9, 2005
Dec 5, 2008
Sep 7, 2001
Dec 17, 1976
Jul 2, 1986
Dec 11, 1981
Jun 12, 1998
May 27, 2020
Feb 10, 2022
Touchstone Pictures
US
Working Title Films
GB
Dogstar Films
New Crime Productions
United Kingdom
United States
Dansk
English