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.
- Genre: Drama, Comedy, Romance, Music
- Studio: Buena Vista Pictures, Touchstone Pictures, Working Title Films, New Crime Productions, Dogstar Films
- Keyword: chicago, illinois, music record, rock 'n' roll, disc jockey, pop, ex-girlfriend, music journalist, relationship problems, record label, fear of commitment, breaking the fourth wall, falling in love, break-up, record, record album, music scene, breaking up with boyfriend, music culture, record store, top five, flashbacks, dating history
- Cast: John Cusack, Iben Hjejle, Todd Louiso, Jack Black, Lisa Bonet, Catherine Zeta-Jones