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
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