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.
as Rob Gordon
as Laura
as Dick
as Barry Judd
as Marie DeSalle
as Charlie Nicholson
as Liz
as Ian Raymond
as Vince
as Justin
as Sarah Kendrew
as Penny Hardwick
as Caroline Fortis
as Alison Jr. High
as Rob Jr. High
as Laura's Mom
as Anaugh Moss
as Barry's Customer
as Beta Band Customer
as Middle Aged Customer
as Rob's Mom
as Laura's Sister Jo
as Minister
as Girl - 19 year old
as Paul
as Miranda
as Alison's Mom
as Kevin Bannister
as Boy In Park
as Chris Thompson
as Rock Guy
as Mourner
as Mourner
as Marco
as Bruce Springsteen
as Louis
as Man In Store
as Party Guest
as Party Guest
as Party Guest
as Party Guest
as Party Guest
as Party Guest
as Piano Player
as Greenday Girl
as Skateboarder
as Flea Market Musician
as Bartender
as Laura's Friend
as Operator (uncredited)
as Glam Rocker (uncredited)
as Guy in Chem Lab (uncredited)
as Laura's Mom (voice) (uncredited)
as Woman Selling Records (DVD version) (uncredited)