An ambitious teen analogue of The Great Gatsby, Gordon Korman’s new novel, Jake, Reinvented, makes explicit its literary antecedents: Jay and Daisy have been replaced by Jake and Didi; Tom and Nick by Todd and Rick. Affluent Long Island in the 1920s has been relocated to a contemporary suburban high school called F. Scott Fitzgerald High. Korman even opens the novel with a portentous epigraph from Gatsby, and playfully dedicates it “For Jay and Daisy.”

In Korman’s retelling, the beautiful people all play on the football team. Rick Paradis, the story’s dyspeptic narrator, succinctly defines his social ranking: “I was the kicker and backup QB. Second fiddle to Todd. Story of my life.” But Todd’s Olympian position is threatened by Jake Garrett, a new student who manages to win a coveted position on the football team, and within days establish himself as the Zeus of Cool with his unrivalled house parties. As one character puts it: “The guy is like a walking zone of happening, and everybody wants to breathe the rare air.”

What Jake’s really after, of course, is Todd’s girlfriend, the über-babe Didi. This is no new craving: two years ago, Didi and Jake attended the same school, when Jake was but a geeky brainiac. Now he has utterly reinvented himself, all in the hopes of winning Didi’s affections. Rick, a friend of all the characters, is uniquely positioned to witness the ensuing drama.

When I read The Great Gatsby in high school, it made almost no impression on me, its setting and concerns seemed so removed from my life. But Korman has wisely seen that the whole notion of reinventing oneself has huge resonance with young readers. What teenager, especially one who has felt himself stranded on the social periphery, has not been beguiled by the possibility of a makeover, a chance to rise to popularity and power? And what teenager isn’t an expert in unrequited love?

Korman has written more than 40 novels for children and young adults, many of them benignly humorous, rambunctious school stories. Jake, Reinvented certainly marks a change of tone, for it is surprisingly, refreshingly cynical in its depiction of teenagers and high school life. Todd is boorish, disloyal, and self-important; Didi is repellently vapid and cowardly; Jennifer (Didi’s confidante) has enthusiastically adopted the mantra “it’s all about me.” Jake is undeterred by the fact that the object of his heart’s desire is completely unworthy. Rick, despite his many social connections, is very much alone throughout. Korman parallels the moral dissipation in Gatsby with Jake’s cycle of increasingly drunken and destructive house parties – and Jake’s ultimate downfall at the hands of the people he thought were friends.

The dearth of sympathetic characters, though intentional, makes this a difficult novel to warm to. Rick is the sole possessor of a moral compass, but his narrative voice sometimes suffers from a television blandness, not just in the dialogue (which I’m willing to admit may be an accurate depiction of teen talk) but more critically in the exposition. Witness the novel’s opening party scene: “The carpet smelled like beer already, so I knew the festivities had been going on for a while. The stereo must have set somebody back a few bucks, because when the bass was cranked, you could feel the air move. The floor was moving too, under the stomping feet of a mob of dancers. Arms and legs jostled the shiny keg, which sat in a little kids’ inflatable wading pool by the living room.” By the time a demented football player heaves the empty keg through a large window, we’ve seen it all a hundred times before, and there’s something vaguely dishonest and ersatz about it. Here, and elsewhere, Korman’s writing feels lazy, all celluloid surface.

Similarly, Korman’s portrayal of Jake Garrett never quite manages to bestow upon him the desired aura of charisma, mystery, and passion. Plenty of characters talk about how cool he is, but as readers we don’t witness enough of this. He dresses like a fashion catalogue, calls everyone “babe” (surely a rather dated affectation), has the winning “Jake smile,” and is unperturbed by the party carnage regularly inflicted on his absent father’s house. Only rarely did I get a visceral sense of Jake’s desperate longing and determination, as when Rick contemplates how Jake must have toiled obsessively to make the football team: “Every time I closed my eyes, I had a vision of Jake, crouched in his backyard all summer in the broiling heat, long-snapping footballs at a target, or maybe an old tire against the side of the house. In my dream, he was drenched in sweat, his spine aching from the unnatural position, the back of his neck roasted and blistering in the sun. Every few snaps, he’d have to chase down his footballs and start the whole process over again. But there, hovering just above the heat shimmer, was Didi’s face. And making the team brought him a step closer to her, so he plodded on.”

Here, Korman shows how well he can write, achieving a poignant tone, and really conveying the pathetic nature of Jake’s doomed quest. Where Korman also shows his stripes is in the comic scenes – not surprising since he has built his career as a humorist. Though his stories often fall back on practical hijinks and belaboured gags (which are hilarious to kids, tedious to adult readers), Korman has always been able to generate truly inspired comic moments. In Jake, Reinvented, he creates a minor character called Dipsy, a cryptic oddball who, though ritually abused by the football players at every party, is nonetheless their biggest, most vocal (and perhaps most vengeful?) fan at every game, bellowing “ALL THE WAY, TEAM! WE’RE GOING ALL THE WAY!” despite the fact the team, miserably third-rate, is invariably being slaughtered on the field.

Korman also achieves a kind of Animal House hilarity with Nelson Jaworski, a psychotic football player feared by opponents and teammates alike. As Rick reports at yet another losing game: “The pathetic amount of resistance offered up by our defense on the opening drive convinced Coach Hammer that he’d better unbench Nelson. So what if the guy had nearly converted our locker room to a pile of rubble? If all his anger could be channeled into a tackle or two, it was worth the risk of putting him out amongst humans.”

Writing a homage to a literary masterpiece is always a risky proposition; it invariably invites comparison. But given my own tepid teenage reaction to The Great Gatsby, I’m willing to bet that Jake, Reinvented, though flawed, may well speak more successfully than Gatsby to high school students about the nature of thwarted ambition and unrequited love.