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"A comedy about fear of commitment, hating your job, falling in love and other pop favorites."
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".
53 Cast Members
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
