Synopsis
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".
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
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

Margaret Travolta
Rob's Mom

Jillian Peterson
Laura's Sister Jo
Dick Cusack
Minister

Susan Yoo
Girl - 19 year old
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