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.

• Touchstone Pictures
• Working Title Films
• John Cusack
• Iben Hjejle
• Todd Louiso
• Jack Black
• Lisa Bonet
• Catherine Zeta-Jones
• Joan Cusack
• Tim Robbins