Watch High Fidelity Online

The book and film have essentially similar plots, though the setting, originally London, is moved to Chicago in the film. Cusack plays Rob Gordon (Rob Fleming in the novel), a record store owner in his 30s whose girlfriend Laura (Hjejle) has just left him before the start of the film. This breakup leads Rob to recall his five most memorable breakups and to wonder what happened to them and why they left him.

Eventually, Rob's re-examination of his failed relationships (brought on by a lucid dream dialogue with Bruce Springsteen in the film adaptation) leads to his decision to seek them all out. Rob revisits all of his past girlfriends as a sort of closure to that part of his life. Rob soon discovers that his ex girlfriends were much different. More often than not he is surprised he ever fell in love with them at all, and in no case is this more evident than when he meets old college classmate Charlie (Zeta-Jones) again, a woman whom we previously learn had left Rob for another man. Rob goes in great detail about his admiration for Charlie before maturing into seeing Charlie for how she really is.

While this search is happening, Rob is struggling to come to grips with Laura leaving him, and throughout the movie we learn about their relationship through narrative flashbacks and monologues. It is during this time that Laura begins dating Ian (Robbins), who was formerly a neighbor of Rob. This relationship causes Rob sleepless nights as he imagines Laura with another man and fears Laura will leave him for real.

To make things worse, Ian is "awful" according to Rob. He plays world music and "awful cooking smells" emanate from his apartment. Despite all of this, Rob is desperate to get Laura back and goes so far as to lurk outside Ian's apartment waiting for her to come out. The interactions between Rob and Ian are humorous to the viewer, but the conflict invariably drives Laura farther away from Rob.

The main turning point of the film comes when Laura's father passes away and Laura invites Rob to the funeral. After the service, Laura propositions Rob for a brief tryst in Laura's car, desirous to feel something besides grief. Laura states that it's not worth the effort to not date Rob and she feels she needs someone in the coming months to help her cope.

Rob resolves his ongoing desire to be interested in other women by realizing that they're only fantasies, since he hasn't seen their negative, less-appealing sides while his relationship with Laura is impartial. He decides that the overall happiness and fulfillment his relationship with Laura brings are worth the occasional downsides.

A major setting in the movie where much interaction and humor take place is the record shop that Rob owns, Championship Vinyl, located at Honore and Milwaukee Streets. Rob and his employees, Dick (Louiso) and Barry (Black), spend their free moments discussing mix-tape aesthetics and constructing "top-five" lists which demonstrate their knowledge of music. Much of the movie focuses on discussions and opinions on artists and music.

Both store workers have unique identities and play an important role in the film. Barry is an overly obnoxious clerk who goes out of his way to make fun of those who he deems lower than him because of their lack of musical knowledge. Dick, on the other hand, is quieter and less forceful with his opinions.

The two separate parts of the story come together when Rob decides to create a record label, Top 5 Records, through the record store. Laura takes this idea even further by setting up an event where Rob ends up DJing and Barry’s newfound band plays in order to promote the new label. The show is a hit and it seems Rob's life is taking a turn for the better.

The film ends with Rob saying that he finally knows what a relationship is all about as he begins to make a new mix-tape for Laura.