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".

Top Cast

John CusackRob Gordon

Iben HjejleLaura

Todd LouisoDick

Jack BlackBarry Judd

Lisa BonetMarie DeSalle

Catherine Zeta-JonesCharlie Nicholson

Joan CusackLiz

Tim RobbinsIan Raymond