Rob Gordon is kind of a jerk. And High Fidelity, based on Nick Hornby’s incisive dissection of the pop-addled male brain, is about the process of him becoming a little less of a jerk. It didn’t seem necessary to point that out 20 years ago, when the film received exactly the niche appreciation it was destined to find, but it does now, because it’s not often we’re given a hero as blinkered as Rob Gordon and not told how we’re supposed to feel about him.

In fairness, Rob is the one doing the telling here, and he’s played by John Cusack, the affable goof of “Savage” Steve Holland comedies like Better Off Dead and One Crazy Summer, and the ingratiating underachiever of Say Anything …, which had established him as a tender romantic soul about a decade earlier. When Cusack was cast as the lead in High Fidelity, it was hard not to think of him as a grownup version of Lloyd Dobler in Say Anything … – just as aimless and uncertain about the future, but coarsened by failed relationships and the grinding inertia of his professional life. Lloyd didn’t want “to sell anything, buy anything or process anything as a career”, but here he is, buying and selling records at Championship Vinyl, a Chicago record store with a location “chosen to attract a minimum of foot traffic”.

The Lloyd Dobler comparison doesn’t hold up much to scrutiny, however. At no point in his life has Rob possessed Lloyd’s earnestness, openness and emotional generosity. At roughly the same age Lloyd was out there escorting the valedictorian around a patch of grass in the parking lot, Rob was breaking up with his girlfriend for not yielding to his aggressive advances. As High Fidelity ticks through his “desert island, all-time top-five most memorable breakups”, Rob gets the opportunity to explain himself directly to the camera – an ingenious solution to the confessional first-person style of Hornby’s book. But it doesn’t mean that we, the jury, are going to find him persuasive. If anything, Rob’s journey through his romantic past reveals how little he’s learned or changed over time. And the film is richer for it.

The film version of High Fidelity has a strange, magical alchemy working for it: an American adaptation of a British novel, written by Americans (Cusack and his writing partners DV DeVincentis and Steve Pink, and Scott Rosenberg) and directed by a Briton (Stephen Frears), with the location shifted from London to the north side of Chicago. There’s a universal quality to guys like Rob Gordon (Fleming in the book), a breed of disaffected Americans and Brits who spent their youth marinating in “sad bastard” music from bands like the Smiths or the Cure, and later insulated themselves in college rock and obscure musical tributaries. The opening narration is potent: “Nobody worries about kids listening to thousands, literally thousands of songs about heartbreak, rejection, pain, misery and loss. Did I listen to pop music because I was miserable? Or was I miserable because I listened to pop music?”

The establishing shot in High Fidelity says everything: as we listen to You’re Gonna Miss Me by the 13th Floor Elevators played on Rob’s stereo – the soundtrack selections throughout remain impeccable – Frears follows the headphone cord to his back profile. Here is a man who cannot get out of his own head, and it’s currently getting pumped with the music that fortified him since adolescence. His long-term girlfriend Laura (Iben Hjejle) is moving out, and while it’s tempting for a snob like him to brush off her career ambitions as selling out, in truth she left because he refused to change so much as a pair of socks for her. That leaves Rob to go through his top five breakups, because he needs to figure out why he always gets dumped.

The brilliance of High Fidelity, carried over from Hornby’s funny, relentlessly self-deprecating book, is that we learn more about Rob from his mission to track down his former girlfriends than he ever learns about himself. He thinks he’s gaining insight into his past – and passing it along to his confidants in the audience – but his behavior in the present is saying everything about why he’s so terrible with women. His first call to the mother of his grade-school make-out partner is a light preview of the petty narcissism to come – he wants her to know that he was “technically” her daughter’s first boyfriend, not the boy she would eventually marry – but it gets darker in a hurry.

John Cusack and Iben Hjejle in High Fidelity.

Photograph: Buena Vista

When Rob catches up to that high-school girlfriend (Joelle Carter), the one who’d resisted his advances, he triggers the longstanding trauma of their breakup, which led to a sexual encounter with another boy she didn’t want (“it wasn’t rape because I said, ‘OK,’ but it wasn’t far off”) and put her off relationships through college. She storms out but he’s elated: he’d dumped her, not the other way around as he’d remembered. It’s the lowest moment for Rob in High Fidelity, funny only in the cavernous depths of blinkered self-absorption that is the true reason why he’s unlucky in love. It doesn’t matter who does the dumping. What matters is that he’s never cared to listen to the women right in front of him.

In retrospect, High Fidelity was a sneakily dark kick-off to a decade where arrested development was the primary theme of comedies about white guys who didn’t have it together. The 40-Year-Old Virgin wouldn’t come along for another five years – and that film and others from Judd Apatow and guests were a little more sweet than sour. But Frears’ film does have the same arc toward maturity, compromise and a healthy adult relationship, and it also has the goofy friend types, Barry (Jack Black) and Dick (Todd Louiso), Rob’s comrades in musical snobbery. The back-and-forth between Barry and Dick is established quickly and hilariously through their choice of music: Dick moping along to the new Belle & Sebastian, Barry whipping his tape across the room in favor of a mix that starts with Katrina & the Waves’ Walking on Sunshine.

One of the film’s most insightful and endearing qualities is how much it’s willing to poke fun at Rob, Barry, and Dick’s record-clerk arrogance without belittling their passions entirely. They have good taste. The music means something to them. And every once in a while, it can connect them to other people. Like when Dick courts a Green Day fan by introducing her to Stiff Little Fingers. (Absolutely no experience more awkward than trying to turn someone on to new music as they’re standing right in front of you.) Or when Barry preaches the gospel of the Jesus and Mary Chain’s Psychocandy. Or when Rob bets he can sell five copies of the Beta Band’s The Three EPs by playing it in the store.

Guys like Rob have perfected the art of the mixtape, of “using someone else’s poetry to express how you feel”, and they give them away like an aural valentine to the women that draw their interest. The elegant insight that Rob finally gleans from his failures with women – failures that are all on him – is that his feelings are only half of the equation and he might want to think about what the person he loves would want to hear. At one point in High Fidelity, after a one-night stand with a singer-songwriter he met at the late, lamented Lounge Ax, Rob says that “what really matters is what you like, not what you are like.” For someone of his pathology, growth is recognizing the opposite is true.