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
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
