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.
John Cusack
Iben Hjejle
Todd Louiso
Jack Black
Lisa Bonet
Catherine Zeta-Jones
Joan Cusack
Tim Robbins
Chris Rehmann
Ben Carr
Lili Taylor
Joelle Carter
Natasha Gregson Wagner
Shannon Stillo
Drake Bell
Laura Whyte
Sara Gilbert
Rich Talarico
Matthew O'Neill
Brian Powell
Margaret Travolta
Jillian Peterson
Dick Cusack
Susan Yoo
Chris Bauer
K.K. Dodds
Marilyn Dodds Frank
Duke Doyle
Aaron Himelstein
Jonathan Herrington
Daniel Lee Smith
Leah Gale
David Darlow
Erik Gundersen
Bruce Springsteen
Alex Désert
Alan S. Johnson
Ian Belknap
Andrew Micheli
Polly Noonan
Philip Rayburn Smith
Michele Graff
Susie Cusack
Liam Hayes
Damian Rogers
Robert A. Villanueva
Joe Spaulding
Scott A. Martin
Heather Norris
Timothy W. Tiedje
James Azrael
Ian Michaels
Susan Hegarty
Beverly D'Angelo