Cusack plays Rob Gordon, the not particularly proud owner of a groovy, largely untrafficked Chicago record shop called Championship Vinyl. As funny as he is forlorn, Rob haunts his treasure vault with his two indispensable if near-intolerable friends, the nervous, fanatical Dick (Todd Louiso, brittle and wry), and the profoundly obnoxious Barry (Jack Black, mouth almighty of Tenacious D). In one of his countless asides to the camera, Rob explains that he hired his fellow thirtysomethings on a part-time basis, but they've insisted upon showing up every day, for the past four years. The reason? These guys adore their work. They while away the hours concocting Top Five lists of songs, records, and entertainments for every imaginable occasion, battling each other with encyclopedic reservoirs of music trivia and otherwise avoiding -- in keeping with a young man's wont -- anything to do with the responsibilities of mortal life on this planet, all with the smug assurance of dealers harboring the finest stash in town. Barry gleefully banishes a hopeful middle-aged man for requesting a copy of Stevie Wonder's "I Just Called to Say I Love You" ("Do you even know your daughter? There's no way she likes that song!"), and Dick ecstatically plies a Green Day fan with an import LP of Stiff Little Fingers. Rob calls them the Musical Moron Twins, but the boffins are also his closest friends, and they keep his floundering business alive, if only vaguely.
Rob's love life is another story, a nearly terminal nadir. His main squeeze, Laura (Iben Hjejle, Danish for "Arquette"), has recently outgrown her adolescent existence, and the ambitious young lawyer leaves Rob for a former neighbor, a ponytailed, New Age aura-balancer named Ian (Tim Robbins, Bodhi trash). This development wrecks Rob's mother (Margaret Travolta), who in turn hammers her son for repeating his rhythmic pattern of domestic failure. Thus, Rob, who never meant to cause Laura any sorrow, explores the ghosts of failed relationships, a special Top Five list of women who eviscerated him, minus Laura, who doesn't initially make the cut. "If you really wanted to mess me up," he bellows at her departing Saab, "you should have got to me earlier!"
Rather than living like a refugee, Rob decides to scan through his heartbreakers, leading us through flashbacks of adolescence, his failed attempt at college, and young adulthood. The first relationship of young Rob (Drake Bell) with playground sweetheart Alison (Shannon Stillo) lasts a total of six hours, ending one day when the girl decides to try kissing a different boy. But the anguish resonates to the present day. As the elder Rob tells us, "It'd be nice to think that, since I was 14, times have changed, relationships have become more sophisticated, females less cruel, skins thicker, instincts more developed. But there seems to be an element of that afternoon in everything that's happened to me since. All my romantic stories are a scrambled version of that first one."
The accuracy of that appraisal is left for us to judge, as Rob's awkward and unpleasant flashbacks continue, prompting him to seek out his former flames, to ask them The Awful Question That Cannot Be Answered: "Why?" Wholesome beauty Penny (Joelle Carter) maintained Carly Simon, Carole King, James Taylor, Cat Stevens, and Elton John on her Top Five list of favorite artists and now works as a film critic (a questionable correlation, although Rob rightly defines her profession as "unspeakably cool"). Shallow beauty Charlie (Catherine Zeta-Jones) used him as cosmetic grist for her mill and now, a few men later, feels love is "too much hard work." With bitter pill Sarah (Lili Taylor) it made sense "to pool collective loathing for the opposite sex ... and share a bed, too," but, with her, Rob discovers he's a man out of time and she's just pills and soap. Besides, Romeo is restless for a vivacious siren named Marie De Salle (Lisa Bonet, tarted up like Lenny Kravitz but inducing no vomiting), who shamelessly croons Frampton and claims wanton coupling as her inalienable right.
Nothing makes much sense for misguided Rob, and the narrative's sole paternal figure is merely a motivational tool, whose death pushes Rob into a new level of understanding. So it's not surprising that the beautiful loser flirts and falls through life, with or without Laura around. He's wildly jealous of the Ian situation (coming to a head in one of the screenplay's wildest, meanest, most gut-bustingly hilarious additions to the book), yet he takes his own high infidelity in stride, using conquests to keep his fractured ego alive. Balancing this rough trade is Laura's prying associate Liz (Joan Cusack, clearly in need of a hot tub and a bundt cake), who hounds Rob about playing doggie style or stalking Ian. Watching this knight in shining vinyl struggle to get happy, get it on, get it together, is at once a sigh and a scream.
Cusack was born to play this role, and he inhabits the soul of Rob with incredible authority, but he's also been working toward this ever since he flailed around with Anthony Michael Hall in Sixteen Candles. Back then, he was just a generic dork, but here he's King Dork, holding what seems like ultimate court, giving Jeff Goldblum's similarly themed dorkfest in The Tall Guy some stiff competition. The eyeliner and the thick hair seem a bit unlikely for this character, but the actor is ripening into maturity, wearing a man's mask of previously undetected worry and strain, and perhaps this is his final kiss-off to dorkdom. After displaying the nobility and rage of a fellow whose primary means of communication is making compilation cassettes, who knows what roles await him?
The four screenwriters and Frears have taken liberties with Nick Hornby's astute, acidic novel, adding Bonet and a subplot about musical skate rats in what seem to be attempts to widen the audience demographic. Of course, transplanting the action from London to Chicago is the shakiest shift, but the affection for the Windy City renders the change about as significant as that of Rob's surname, from Fleming to Gordon. A few lines are swapped and a very funny subplot about a priceless record collection seems to have been shaved at the last minute, but the amputation of Hornby's cynicism and self-loathing seems to be the most damaging surgery. In the book, for instance, the absence of a condom is transformed into a hurtful gesture of abstinence; in the movie, we get a cute and clumsy love scene. The creators have made good use of most of Hornby's wit and woe, but they should have used it all, to intensify both the laughter and the pain, a formula Frears has put to the test in The Snapper and My Beautiful Laundrette.
Hornby's relationship philosophies may be trimmed a little too tidily here, but, thankfully, the novel's pop spirit makes it to the screen unscathed, with a fairly amazing array of blinding tracks and deafening colors. The record shop boys and their snobbery add a constant kick, but, by the end, Rob remembers why music is a gift, and a fine balance is achieved, prompting a popular (and often utterly inaccurate) saying: It's all good.