Rob Gordon (John Cusack) is a man stuck in a rut and that rut is one that occupies childlike sensibilities, an inability to adapt to change, and a lack of understanding, or effort to understand, the women in his life. Rob has yet to really come of age and has been stagnant in his ability to mature and grow up, sticking to what he knows in the most primal sense. He runs a record store with his friends Dick (Todd Louiso) and Barry (Jack Black), spending most of his days engaging in meaningless conversations about which musicians are better than other musicians, what records have a long-lasting impact over others, and so on, almost as if their musical elitism predated the kind you see in the same place where this film is set, Chicago.
Rob has just gone through a breakup with Laura (Iben Hjejle), a woman he clearly cared about but had no idea how to act on his feelings in a way that pleased her in a significant manner. She was troubled by his childishness and he was unwilling to change for the better. Depressed and distraught, finally questioning what role he had to play in his breakups, Rob cycles through five of his old romantic partners to see if there's some sort of consistent screw-up he is faced with in all his relationships.
High Fidelity works instantly because of Cusack's character and character acting abilities. He embodies Rob Gordon, who we grow to find likable at times, mostly thanks to his quick-witted mannerisms and ability to keep a conversation moving, and incorrigible at others, for his inability to realize that he is his own worst enemy. Cusack's "cool guy" approach to the material, complete with first-person narration and frequently employed witticisms, make him nonetheless an interesting protagonist because you can fault him and appreciate him for many reasons, but the main one is that he's human. Louiso and Black work well as the side characters here, in addition, particularly Luiso, who is given some of the funniest lines of the picture. Jack Black is your typical Jack Black character here, but ostensibly boasting more controlled chaos than outright chaos here (either that or his craziness gels well enough with Cusack's coolness that typical results aren't as blatant).
Director Stephen Frears and the quartet of writers at hand here (Cusack himself, D.V. DeVincentis, Steve Pink, and Scott Rosenberg) are commendable because they understand the way males think. If a woman goes through a breakup, as least from what I've seen from my female friends and based off knowledge from films I have seen, she often reevaluates herself, checking herself with her friends to see what could've possibly gone wrong and if she had anything to do with the relationship's demise. Men, from what I've seen from my male friends and other films I have seen, are almost too prideful for that sort of thing, rarely showing too much emotion and holding it in for a rainy day. We move on to hooking up, letting our feelings out to only our closest friends, and simply try to find another woman who will provide us not with the same kind of love but the same feelings as the previous gal did.
Of course I'm speaking in rampant generalities here; the heart of my argument is that so is Frears and his writers. They're evaluating the character based on terms typical of the male psyche, and are effective in at least portraying a pragmatic situation for a character who has been through a plethora of rough breakups. High Fidelity also features the soundtrack from heaven to compliment our leads characters' musical elitism that works to bring life to a screenplay that could've either showed its worn qualities or lessened in impact over time. However, thanks to Cusack as the center of the film, complimented by two other effective actors, the film stands strong and offers us a glimpse into the mind of a male during one of the most vulnerable times in his life.
Starring: John Cusack, Jack Black, Todd Louiso, and Iben Hejejle. Directed by: Stephen Frears.