Summary
When record store owner and compulsive list-compiler Rob Gordon gets dumped by his long-time girlfriend, Laura, because he hasn't changed since they met, he revisits his top five breakups of all time in order to figure out what went wrong. As he examines his failed attempts at romance and happiness, the process finds him being dragged, kicking and screaming, into adulthood.
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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
Lili Taylor
Sarah Kendrew
Joelle Carter
Penny Hardwick
Natasha Gregson Wagner
Caroline Fortis
Drake Bell
Rob Jr. High
Laura Whyte
Laura's Mom
Sara Gilbert
Anaugh Moss
Rich Talarico
Barry's Customer
Brian Powell
Middle Aged Customer
Margaret Travolta
Rob's Mom
Jillian Peterson
Laura's Sister Jo
Susan Yoo
Girl - 19 year old
Chris Bauer
Paul
K.K. Dodds
Miranda
Marilyn Dodds Frank
Alison's Mom
Aaron Himelstein
Boy In Park
David Darlow
Mourner
Bruce Springsteen
Bruce Springsteen
Alex Désert
Louis
Andrew Micheli
Party Guest
Polly Noonan
Party Guest
Philip Rayburn Smith
Party Guest
Scott A. Martin
Bartender
James Azrael
Glam Rocker (uncredited)
Ian Michaels
Guy in Chem Lab (uncredited)
Beverly D'Angelo
Woman Selling Records (DVD version) (uncredited)