John Cusack stars in and co-scripts this adaptation of Nick Hornby's novel about failed romance and pop music obsession, relocated from North London to Chicago. DJ-turned-record shop owner Rob Gordon (Cusack) undergoes a major crisis when his long-term girlfriend Laura (Iben Hjejle) walks out on him. Forced to reassess his previous failed relationships with women, Rob finds little solace with his employees - opinionated would-be rock singer Barry (Jack Black) and introverted, sensitive Dick (Todd Louiso) - who spend more time making compilation tapes and quarrelling over their all-time top five album-opener tracks than selling records. After a one-night stand with singer Marie De Salle (Lisa Bonet), Dick discovers that Laura has moved in with hated ex-neighbour Ian (Tim Robbins), and begins looking up his various exes in an attempt to find out where it all went wrong.