If you’re trying to analyze F. Scott Fitzgerald’s jazz age novel The Great Gatsby and you’re not thinking about Dante’s Inferno, you’re missing an obvious connection.

The connection is easy to spot and hard to dispute, though it rarely comes up in discussion of the book. I haven’t heard it mentioned at all during the big media buildup to the bombastic new Baz Luhrmann/Leonardo DiCaprio Great Gatsby movie that’s opening this weekend, though I have read a few clueless movie-tie-in articles that strain to explain the enduring cultural significance of Fitzgerald’s novel. These articles usually miss the point by describing The Great Gatsby as a novel about the American dream of wealth and success, or something pedestrian like that.

Explanations of Gatsby as a Randian epic about a businessman don’t illuminate the book very well, and neither do theories that Nick Carraway was gay or that Jay Gatsby was African-American. I tend to stick with the standard approach: The Great Gatsby is a chic and tawdry tale of love and romantic illusion. It’s written in lush but light poetic prose in a heated tone that evokes a dramatic sense of spiritual hazard. The spiritual hazard is where Dante comes in.

As a writer, F. Scott Fitzgerald liked to paint modern society in starkly religious or biblical terms. He does not appear to have been very religious, but he was raised Catholic, viewed Christian ideals warmly, and seems to have been especially fascinated with concepts of Satanic guilt and damnation. This is most clear in his titles: his first novel was called This Side of Paradise, his second The Beautiful and Damned. His short stories include: Babylon Revisited, Jacob’s Ladder, Absolution.

But The Great Gatsby, the novel he intended as the pinnacle of his mature literary achievement, is also his most ambitious spiritual work, as it apppears to be loosely grounded upon Dante’s Inferno, the first and most famous part of the Italian poet’s epic The Divine Comedy, in which a traveler is escorted on a colorful guided tour of Hell.

In The Great Gatsby, the journey from East Egg to New York City is the journey into Hell, and the passages that describe the Valley of Ashes that lies between the opulent North Shore of Long Island and Manhattan’s den of sin are as Danteesque as can be:

About half way between West Egg and New York the motor road hastily joins the railroad and runs beside it for a quarter of a mile, so as to shrink away from a certain desolate area of land. This is a valley of ashes — a fantastic farm where ashes grow like wheat into ridges and hills and grotesque gardens; where ashes take the forms of houses and chimneys and rising smoke and, finally, with a transcendent effort, of men who move dimly and already crumbling through the powdery air. Occasionally a line of gray cars crawls along an invisible track, gives out a ghastly creak, and comes to rest, and immediately the ash-gray men swarm up with leaden spades and stir up an impenetrable cloud, which screens their obscure operations from your sight. But above the gray land and the spasms of bleak dust which drift endlessly over it, you perceive, after a moment, the eyes of Doctor T. J. Eckleburg. The eyes of Doctor T. J. Eckleburg are blue and gigantic—their irises are one yard high. They look out of no face, but, instead, from a pair of enormous yellow spectacles which pass over a nonexistent nose. Evidently some wild wag of an oculist set them there to fatten his practice in the borough of Queens, and then sank down himself into eternal blindness, or forgot them and moved away. But his eyes, dimmed a little by many paintless days, under sun and rain, brood on over the solemn dumping ground.

The romantic plight of poor Jay Gatsby — stuck in a karmic cycle of want and pain, constantly borne back upon himself — is another Dante touch. In the Inferno, sinners are seen in tableaus of torture. The main method of torture in Hell, according to Inferno, is to be forced to repeat a desperate act of yearning or suffering through eternity. The sharpest pain is in the repetition. Damned souls stand in boiling muck, choking as they try to raise their heads, or they are forced to stand and push stones against each other, never giving ground. Lost souls are shot by arrows over and over, or are eaten away by beasts and then reconstructed the next day so they can be eaten again, or walk in circles with their heads turned backwards so they can only see their pasts.

This, in Fitzgerald’s novel, is the fate of Jay Gatsby, who is doomed to love (and be whipped by) Daisy Buchanan over and over, who yearns and hopes and proudly declares “You can’t repeat the past? Why of course you can.” It’s also the fate of thoughtless Daisy, and bigoted Tom, and foolish George Wilson, and demonic Meyer Wolfsheim, and almost everybody Nick Carraway meets. (The aptly named Jordan Baker may be an exception, along with Carraway himself.)

I’m not sure why the Danteesque interpretation of The Great Gatsby has never taken wide root, but I’m sure that Fitzgerald had the inspiration in mind. In echoing a classical work, he was following a fruitful literary trend of his time. Immediately preceding The Great Gatsby in 1926, James Joyce’s 1922 Ulysses was a modernist nod to Homer, and T. S. Eliot’s 1922 The Waste Land hearkened back to the medieval legends of King Arthur and the Fisher King.

Thus, The Great Gatsby was intended to be classical in a trendy way. In characterizing New York society in such wide-eyed diabolical terms, Gatsby is also the kind of urban portrait that only an outsider like F. Scott Fitzgerald, the eternal Midwesterner, could write. It is a harsh picture of New York City, of course; the Plaza Hotel on 59th Street and Fifth Avenue is apparently the ninth circle of Hell.

But, then, Fitzgerald also paints his infernal city as beguiling and magnetic. He clearly adores the place. Always in doubt about the moral condition of his own soul (The Crack-Up would follow Gatsby), Fitzgerald clearly sympathized with and related to the suffering lost souls of his novel, even as his moralistic narrator looks away in disgust. Dante Alighieri did the same thing in The Inferno.

I’ve written on this blog about The Great Gatsby before, especially regarding my search for the real-life locale of the Valley of Ashes, and about the sign factory that stands mysteriously at the spot to this day. I’ll be sure to write about it again after I see the much-hyped new Baz Lurhmann movie that’s about to open this weekend. (My expectations are mixed: I like Baz Lurhmann, I think Leo DiCaprio is an awful actor, and I don’t get why 3D is a good idea.) Until I get a chance to write about the film, I’d love to hear from you about it — have you caught the flick yet?