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".
Cast
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
Mourner
Erik Gundersen
Marco
Bruce Springsteen
Bruce Springsteen
Alex Désert
Louis
Alan S. Johnson
Man In Store
Ian Belknap
Party Guest
Andrew Micheli
Party Guest
Polly Noonan
Party Guest
Philip Rayburn Smith
Party Guest
Michele Graff
Party Guest
Susie Cusack
Party Guest
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)
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