The book and film have essentially similar plots, though the setting, originally London, is moved to Chicago in the film. Cusack plays Rob, a record shop owner in in his 30s whose girlfriend Laura (Hjejle) has just left him. At the record shop, he and his employees Dick (Todd Louiso) and Barry (Black) spend their free moments constructing "top five" lists of anything that demonstrates their knowledge of music.
Rob, recalling his five most memorable breakups, sets about getting in touch with the former girlfriends, including Charlie (Zeta-Jones) and Sarah (Taylor).
Eventually, Rob's re-examination of his failed relationships (egged on in a lucid dream dialogue with Bruce Springsteen), and the death of Laura's father bring the two of them back together. Their relationship is cemented by the launch of a new purposefulness to Rob's life, which in the book is the revival of his disc jockey career, and in the film, the launch of his new record label.
For audiophile sound systems, see High fidelity.