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The best advice I ever got about reading came from the critic and scholar Louis Menand. Back in 2005, I spent six months in Boston and, for the fun of it, sat in on a lit seminar he was teaching at Harvard. The week we were to read Gertrude Stein’s notoriously challenging Tender Buttons, one student raised her hand and asked—bravely, I thought—if Menand had any advice about how best to approach it. In response, he offered up the closest thing to a beatific smile I have ever seen on the face of a book critic. “With pleasure,” he replied.

I have read The Great Gatsby five times. The first was in high school; the second, in college. The third was in my mid-twenties, stuck in a remote bus depot in Peru with someone’s left-behind copy. The fourth was last month, in advance of seeing the new film adaptation; the fifth, last week. There are a small number of novels I return to again and again: Middlemarch, The Portrait of a Lady, Pride and ­Prejudice, maybe a half-dozen others. But Gatsby is in a class by itself. It is the only book I have read so often despite failing—in the face of real effort and sincere ­intentions—to derive almost any pleasure at all from the experience.

I know how I’m supposed to feel about Gatsby: In the words of the critic Jonathan Yardley, “that it is the American masterwork.” Malcolm Cowley admired its “moral permanence.” T. S. Eliot called it “the first step that American fiction has taken since Henry James.” Lionel Trilling thought Fitzgerald had achieved in it “the ideal voice of the novelist.” That’s the received Gatsby: a linguistically elegant, intellectually bold, morally acute parable of our nation.

I am in thoroughgoing disagreement with all of this. I find Gatsby aesthetically overrated, psychologically vacant, and morally complacent; I think we kid ourselves about the lessons it contains. None of this would matter much to me if Gatsby were not also sacrosanct. Books being borderline irrelevant in America, one is generally free to dislike them—but not this book. So since we find ourselves, as we cyclically do here, in the middle of another massive Gatsby ­recrudescence, allow me to file a minority report.

The plot of The Great Gatsby, should you need a refresher, is easily told. Nick Carraway, an upstanding young man from the Midwest, moves to New York to seek his fortune in the bond business. He rents a cottage on Long Island, next to a mansion occupied by a man of mysterious origins but manifest wealth: Jay Gatsby, known far and wide for his extravagant parties. Gradually, we learn that Gatsby was born into poverty, and that everything he has acquired—­fortune, mansion, entire persona—is designed to attract the attention of his first love: the beautiful Daisy, by chance Nick’s cousin. Daisy loved Gatsby but married Tom Buchanan, who is fabulously wealthy, fabulously unpleasant, and conducting an affair with a married working-class woman named Myrtle. Thanks to Nick, Gatsby and Daisy reunite, but she ultimately balks at the prospect of leaving Tom and, barreling back home in Gatsby’s car, kills Myrtle in a hit-and-run. Her husband, believing that Gatsby was both the driver and Myrtle’s lover, tracks him to his mansion and shoots him. Finis, give or take some final reflections from Nick.

When this tale was published, in 1925, very few people aside from its author thought it was or would ever become an American classic. Unlike his first book—This Side of Paradise, which was hailed as the definitive novel of its era—The Great Gatsby emerged to mixed reviews and mediocre sales. Fewer than 24,000 copies were printed in Fitzgerald’s lifetime, and some were still sitting in a warehouse when he died, in 1940, at the age of 44. Five years later, the U.S. military distributed 150,000 copies to service members, and the book has never been out of print since. Untold millions of copies have sold, including 405,000 in the first three months of this year.

But sales figures don’t capture the contemporary Gatsby phenomenon. In recent years, the book has been reinvented as a much-admired experimental play (Gatz) and a Nintendo video game—“Grand Theft Auto, West Egg,” as the New York Times dubbed it. This Thursday, Stephen Colbert will host a Gatsby book club; the new movie opens Friday. (Read David Edelstein’s review here.) If you need a place to take your date afterward and have $14,999 to spare, you can head to the Trump hotel, which is offering a glamorous “Great Gatsby Package”: three nights in a suite on Central Park West, a magnum of Champagne, cuff links and a tailored suit for men, and, “for the ladies, an Art Deco shagreen and onyx cuff, accompanied by a personal note from Ivanka Trump.” Car insurance is not included.

So Gatsby is on our minds, on our screens, on our credit cards, on top of the Amazon best-seller list. But even in quieter days, we never really forget Fitzgerald’s novel. It is, among other things, a pedagogical perennial, in part for obvious reasons. The book is short, easy to read, and full of low-hanging symbols, the most famous of which really do hang low over Long Island: the green light at the end of Daisy’s dock; the unblinking eyes of Dr. T. J. Eckleburg, that Jazz Age Dr. Zizmor. But the real appeal of the book, one assumes, is what it lets us teach young people about the political, moral, and social fabric of our nation. Which raises the question: To our students, and to ourselves, exactly what kind of Great Gatsby Package are we selling?

I will grant Fitzgerald this much: Somehow, in the five years between his literary debut and The Great Gatsby, he taught himself to write. This Side of Paradise is intermittently brilliant but terrifically uncontrolled. Gatsby, by contrast, is focused and deliberate: a single crystal, scrupulously polished.

It is an impressive accomplishment. And yet, apart from the restrained, intelligent, beautifully constructed opening pages and a few stray passages thereafter—a melancholy twilight walk in Manhattan; some billowing curtains settling into place at the closing of a drawing-room door—Gatsby as a literary creation leaves me cold. Like one of those manicured European parks patrolled on all sides by officious gendarmes, it is pleasant to look at, but you will not find any people inside.

Indeed, The Great Gatsby is less involved with human emotion than any book of comparable fame I can think of. None of its characters are likable. None of them are even dislikable, though nearly all of them are despicable. They function here only as types, walking through the pages of the book like kids in a school play who wear sashes telling the audience what they represent: OLD MONEY, THE AMERICAN DREAM, ORGANIZED CRIME. It is possible, of course, to deny your readers access to the inner lives of your characters and still write a psychologically potent book: I give you Blood Meridian. But to do that, you yourself must understand your characters and conceive of them as human.

Fitzgerald fails at that, most egregiously where it most matters: in the relationship between Daisy and Gatsby. This he constructs out of one part nostalgia, four parts narrative expedience, and zero parts anything else—love, sex, desire, any kind of palpable connection. Fitzgerald himself (who otherwise expressed, to anyone who would listen, a dazzled reverence for his own novel) acknowledged this flaw. Of the great, redemptive romance on which the entire story is supposed to turn, he admitted, “I gave no account (and had no feeling about or knowledge of) the emotional relations between Gatsby and Daisy.”

What was Fitzgerald doing instead of figuring out such things about his characters? Precision-engineering his plot, chiefly, and putting in overtime at the symbol factory. Gatsby takes place over a single summer: three months, three acts, three chapters each, with a denouement—the car accident and murder—of near-Greek (but also near-silly) symmetry. Inside that story, almost everything in sight serves a symbolic purpose: the automobiles and ash heaps, the upright Midwest and poisonous East, the white dresses and decadent mansions.

Heavy plot, heavy symbolism, zero ­psychological motivation: Those are the genre conventions of fables and fairy tales. Gatsby has been compared to both, typically to suggest a mythical quality to Fitzgerald’s characters or a moral significance to his tale. But moral significance requires moral engagement: challenge, discomfort, illumination, or transformation. The Great Gatsby offers none of that. In fact, it offers the opposite: aloofness.

Scott Fitzgerald was, in his own words, “a moralist at heart.” He wanted to “preach at people,” and what he preached about most was the degeneracy of the wealthy. His concern, however, did not lie with the antisocial behaviors to which the rich are prone: acquiring their wealth through immoral means, say (Gatsby manipulates the American financial system and dies a martyr), or ignoring all plights from which they have the means to protect themselves. Like many American moralists, Fitzgerald was more offended by pleasure than by vice, and he had a tendency to confound them. In The Great Gatsby, polo and golf are more morally suspect than murder. Fitzgerald despised the rich not for their iniquity per se but for the glamour of it—for, in H. L. Mencken’s words, “their glittering swinishness.”

Yet Fitzgerald also longed to be a glittering swine himself, and acted like one anytime he could afford it. “All big men have spent money freely,” he wrote in a letter to his mother. Given the means, he was only too happy to drape Zelda in furs, buy up the local Champagne supply, and throw Gatsby-worthy parties. These conflicted feelings about wealth bled into his work—and in fiction, as in life, piety and swinishness pair poorly. On the page, Fitzgerald’s moralizing instinct comes off as cold; the chill that settles around The Great Gatsby is an absence of empathy. The glittering swinishness, by contrast, sometimes serves him well: There’s a reason Gatsby contains the best party scenes in American literature. But when you combine the two—when you apply a strict moral code to the saturnalian society to which you are attracted—you inevitably wind up a hypocrite. Jonathan Franzen once described Gatsby as “the central fable of America.” If so, it is the fable of the fox and the grapes: a story about people who criticize precisely what they covet.

That’s an interesting tension, common to most of us and great fodder for fiction. But rather than explore it, Gatsby enacts it. As readers, we revel in the glamorous dissipation of the rich, and then we revel in the cheap satisfaction of seeing them fall. At no point are we made to feel uncomfortable about either pleasure, let alone their conjunction. At no point are we given cause, or room, to feel complicit. Our position throughout is that of an innocent bystander. That’s also Nick’s role, so the perspective of the book becomes one of passive observation. He watches across apartments as affairs take place, across parties as fights break out, across the road where the dead Myrtle’s left breast flaps leerishly loose. Yet he never admits to collusion with or seduction by all the fabulous depravity around him. After it’s all over, he retreats to the Midwest and, figuratively and literally, tells his story from the safe remove of America’s imaginary moral high ground.

In This Side of Paradise, in many of his short stories, and especially in his nonfiction, Fitzgerald displays a quick and often mordant wit. Then, suddenly, that voice vanishes; The Great Gatsby might be the least funny book about rich people ever written. The British, who kick our ass at writing about class, know how useful a dash of humor is—how it can lift up or deflate, jostle or soothe, comfort or eviscerate. (In a literary hostage exchange, I would trade a thousand Fitzgeralds for one Edward St. Aubyn, 10,000 for an Austen or Dickens.) In leaving that note out, Fitzgerald is not just making a stylistic choice, nor even just signaling his solemnity of purpose. He is all but inventing a new narrative mode: the third-­person sanctimonious. From the story of America’s self-consuming profligacy, corruption, and avarice, he omits himself and his moral proxy—and, by extension, us.

I can only sketch here the many other things that trouble me about Gatsby and its place in our culture. There is the convoluted moral logic, simultaneously Romantic and Machiavellian, by which the most epically crooked character in the book is the one we are commanded to admire. There’s the command itself: the controlling need to tell us what to think, both in and about the book. There’s the blanket embrace of that great American delusion by which wealth, poverty, and class itself stem from private virtue and vice. There’s Fitzgerald’s unthinking commitment to a gender order so archaic as to be Premodern: corrupt woman occasioning the fall of man. There is, relatedly, the travesty of his female characters—single parenthesis every one, thoughtless and thin. (Don’t talk to me about the standards of his time; the man hell-bent on being the voice of his generation was a contemporary of Dorothy Parker, Gertrude Stein, and Virginia Woolf, not to mention the great groundswell of activists who achieved the passage of the Nineteenth Amendment. Yet here he is in A Short Autobiography: “Women learn best not from books or from their own dreams but from reality and from contact with first-class men.”)

I can’t say more here about any of these. But allow me, in its fullness, one last apostasy. Every time I read the book’s beloved final line, I roll my eyes. “So we beat on, boats against the current, borne back ceaselessly into the past”: What a shame that Fitzgerald wasted such a lovely image on such an insufferable voice. Even as that faux “we” promises intimacy, the words drift down to us from on high—condescending, self-serious, detached from genuine human struggle. I’m sorry, but in the moral universe of The Great Gatsby, we are not all in the same boat. We are all up above it, watching—with prurient fascination, with pious opprobrium, watching and watching and doing nothing at all.

*This article originally appeared in the May 13, 2013 issue of New York Magazine.