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.
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 pony-tailed, 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 5 list of women who eviscerated him, minus Laura, who doesn't initially make the cut.
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) included Cat Stevens on her Top 5 list of favorite artists and is now a film critic. Shallow beauty Charlie (Catherine Zeta-Jones) used him as cosmetic grist for her mill and now 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), who shamelessly croons Frampton and claims wanton coupling as her inalienable right.
Nothing makes much sense for misguided Rob. 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), 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.
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. The creators have made good use of most of Hornby's wit and woe, but they should have used it all, to intensify the laughter and the pain.
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): It's all good.