Writing a history of money in literature is as hopeless a task as writing a literary history of love. Like love, or happiness, or truth, money is so vast, protean and mirrorlike a concept that it turns up everywhere. Money has been compared to death, life, blood, shit, sex, guts, oil, water, air, earth, fire, laughter, knowledge, God, the devil — in fact, like the Freudian phallus (and it’s been compared to that, too) you’ve got to look hard to find something it hasn’t been compared to. Once you start looking for money, it turns up everywhere: Every book, every story — even nursery rhymes — rings like a cash register. Jack and Jill went up the hill to fetch a pail of water — because they couldn’t afford indoor plumbing.

Still, out of this lucrative multitude, certain works engage more deeply with money, investigate or embody more deeply the infinite range of passions, desires, nightmares and insights loot stirs. From the most stirring exhortations against greed to the most delicious exaltations of the long green, from calm gilt-edged prose to stake-it-all-on-one-throw writing that explodes like a booby-trapped bag of stolen bank bills, it’s all there. The most dirty, desired and empty of human possessions, money is a screen on which is projected the myriad personalities of its chroniclers, and the values of the times in which they wrote, like nothing else. What follows is a brief tour of some of the literary works that, in the words of the poet, hold on to the dollar till the eagle grins.

Money gets a bad press from the outset. The two major sources of Western literature, the classical tradition and Christianity, share a mistrust of money — a noble sentiment that tends to break down in the real world. Plato acknowledges the necessity of money but denies it can bring happiness and assigns it the lowest place in a hierarchy of soul, body and money. In one of the juicier moments in the Dialogues, Socrates carves up a fatuous Sophist named Hippias, who claims to be wiser than his philosophical opponents because he has made more money (possibly the earliest appearance of the venerable “if you’re so smart, why aren’t you rich” argument so popular among logicians of the School of Newt). “According to your account, earlier thinkers were sunk in ignorance,” Socrates sarcastically observes, before asking Hippias in which of the cities he visited he made the most money — a subversive line of questioning that quickly reduces the boastful cash cow to desperate bluster.

In the creation-myth section of “The Metamorphoses,” the Latin poet Ovid relates that money entered the world in the last, debased age of iron, when “men explored the world’s very bowels, and dug out the wealth which it had hidden away, close to the Stygian shades.” Aristotle, in the “Politics,” asserts that those who pursue limitless wealth (as opposed to those who aim at limited wealth as a means to an end) are “intent upon living only, and not upon living well; and, as their desires are unlimited, they also desire that the means of gratifying them should be without limit” — a searing formulation that falls through time and literature for 1600 years, ending up drifting like a crumpled leaf on Jay Gatsby’s swimming pool.

The Bible, of course, also casts a disapproving eye upon money. Matthew 6:24 says, “No man can serve two masters; for either he will hate the one, and love the other; or else he will hold to the one, and despise the other. Ye cannot serve God and money.” In a larger sense, the very story of Man’s fall is the story of money: Before Eve plucked the apple, greenbacks did not exist. Ever since then, cash has given off a faint whiff of the illicit Gravenstein — or a more pungent odor.

In John of Salisbury’s 12th century “The Body Social,” John rehearses the well-known conceit in which various members of society are compared to the parts of the human body. The prince is the head, the Senate the heart, judges the eyes. And those who are in charge of business? “Financial officers and keepers … may be compared with the stomach and the intestines.” This may not be precisely the anatomical role that Donald Trump imagines himself playing, but judging from the portion of the body to which the Donald is most frequently compared by his contemporaries, Salisbury’s theory should not simply be wiped off.

Of course, the Christian rejection of worldly things was compromised from the beginning: Christ’s “render unto Caesar the things that are Caesar’s” provides the Scriptural justification for all kinds of future accommodations with the state and wealth. Nor was the Classical Age all high-minded denunciations of money. Ancient comedy, which like all comedy deflates Big Ideals and gratifies earthly wishes, is money-positive: in Aristophanes’ “The Birds,” the heroes, fugitives from Athenian taxation, blockade the gods so they can’t enjoy the sacrifices made to them on earth. The gods capitulate.

One of the delightful things about the literature of money is its recurrent craziness. One of the wildest things ever written about money is found in Petronius’ “Satyricon” (ca A.D. 60), which some call the first novel ever written. “Trimalchio’s Feast,” the largest part of this fragmentary work, is one of the all-time great depictions of excess — monetary, sexual, gustatory. The narrator and his oversexed pals are feted by Trimalchio, a merchant of frightening and obscene wealth, in the most lurid, vulgar and over-the-top banquet since George Bush puked on his Japanese host. As the guests stuff their faces with their gross host’s nauseatingly ornate food — pigs stuffed with live thrushes, etc. — they discourse on the amorality of modern times. “We’re in it for bad times,” one guest laments between belches. “And you know why? Because no one believes in the gods, that’s why. Who observes the fast days anymore, who cares a fig for Jupiter? One and all, bold as brass, they sit there pretending to pray, but cocking their eyes on the chances and counting up their cash.” Petronius’ voice is at once so ironic and hedonistic that it is impossible to sort out his revulsion at Trimalchio’s excess from his enjoyment in it — a complicated attitude, half sleazy, half moral, that pops up again a couple of millennia later in Martin Amis’ grotesquely entertaining “Money: A Suicide Note” (1984).

In the popular literature of the Middle Ages and the early Renaissance, anti-money strictures dominate. As Johan Huizinga points out in “The Waning of the Middle Ages,” the contrast between wealth and poverty in the days of feudalism was brutally obvious, and consequently the misdeeds of the rich — who were thought to be fixed in their state by divine decree — aroused enormous outrage. Cautionary tales were common, but the age’s relationship to money is more complex. The unworthy rich are denounced, but often with an undercurrent of green-eyed irritation that often comes close to outright emulation of the “wicked” character. Thus we find the stock figures of the randy friar, his tumescent purse bulging as he reaches merrily into the hapless merchant’s wallet and his wife’s cleavage; and the miser, the suspicious, impotent moneybags whose icky congress with a hot babe is solely due to his cash. But the gusto with which these moist-palmed friars and horny old coupon-clippers are portrayed threatens to obliterate the pious message. To engage with the miser can be to accept his terms, to desire what he desires. Like Chaucer’s nightmarish Pardoner, who cynically uses the Biblical text “Radix malorum est cupiditas” (greed is the root of all evil) to squeeze money out of his flock, writers who start out attacking money often end up pimping for it.

Until the democratic age, literature is dominated by the metaphor of the Wheel of Fortune. Money is one tangible manifestation of Fortune, but for most of literary history society was too fixed and hierarchical, both in terms of class and money, to allow writers to explore the different points on Fortune’s wheel. One who did was the sui generis 15th century poet Frangois Villon, who captured the vicissitudes of his own tortured, sensual life in agonized, mocking, naked poems that are filled with references to sex, the city and money. His poem “The Legacy” (translated by Galway Kinnell) ends: “Done on the aforesaid date/By the very renowned Villon/Who doesn’t eat, shit or piss,/Dry and black like a furnace mop/He doesn’t have a tent or pavilion/That he hasn’t left to a friend/All he’s got left is a little change/That will soon come to an end.”

It is no coincidence that the sound of jingling coins should echo through the work of the first great poet of the city. For money and urban life go together. The city is the place where everything circulates, where the vertical structures of aristocratic society are overthrown by the power of trade, of commerce, of money. Money does not come into its own as a subject until the city, in all its unruly, democratic splendor, defeats the court.

This process begins in the Renaissance, as writers subject the Christian view of money to a searching, sometimes ironic inquisition. In Cervantes’ “Don Quixote” (1615), for example, Don Quixote’s first adventure takes him to an inn, where he mistakes some whores for great ladies. When he prepares to spend the night, the innkeeper asks if he has any money. “‘Not a cross,’ reply’d the Knight, ‘for I never read in any History of Chivalry that any Knight-Errant ever carry’d money about him.’” The innkeeper argues that the knights did carry money but that the “Authors (thought) it needless to mention Things so evidently necessary as Money and clean Shirts,” and he commands the knight to “never from this time forward ride without Money.” The exchange might sum up the whole history of money in literature. The innkeeper’s command has come true: Money is a monkey writers have never since been able to shake off their back.

The greatest writer of the Renaissance, Shakespeare, is a universe, and within that universe there are several planets dedicated to money. In general, Shakespeare’s attitude toward money follows the standard aristocratic/Christian/classical position: His most ferocious villain, Iago, incites his dupe Roderigo with the refrain “Put money in thy purse,” and those characters who seek avidly to get rich are usually seen as base-born clowns, if not outright knaves.

Shakespeare’s best-known play on a monetary theme is “The Merchant of Venice” (1595), which denounces the idolatrous, legalistic profit-love of Shylock. Despite the complexity of Shylock’s character, however, the play takes a fairly received view of money, as evidenced by platitudes like the famous, “All that glisters is not gold” speech in the casket scene.

A much more intense analysis of money is found in “Timon of Athens” (1607), which tells the story of a wealthy, rashly generous man whose “friends” disappear when his money does. The story is hackneyed, but Shakespeare, through Timon, extends it into an audacious, almost hallucinatory thesis: The mere existence of money means that the entire universe is based on theft. With maniac similes that recall Lear, Timon rants: “The sun’s a thief, and with his great attraction/Robs the vast sea;
the moon’s an arrant thief,/And her pale fire she snatches from the sun … each thing’s a thief.” In the play’s most memorable scene, Timon, as mad and misanthropic as Lear, roots in the earth and digs up a treasure of gold. The stark physicality of the madman digging up that which he can no longer use reveals the strangeness of the very idea of wealth.

As the Renaissance faded into the increasingly mercantile 16th and 17th centuries, the ancient division of society into “estates” — king, clergy, aristocrats, merchants, peasants — began to break down. By the 18th century, money was finally stripped of its lingering religious association with the higher orders: It had not yet become an idol itself, but its corrosive power was undeniable. Concomitantly, literature was no longer produced only by members of the elite classes: More and more writers appeared who had experienced, like Villon, the ups and downs of Fortune. The result was a literature of a gritty new realism and individualism that found its voice in the great realist literary form, the novel.

For all the brilliance and vehemence of its rhetoric, a work like “Timon” appears almost sentimental when compared to a work like Daniel Defoe’s “Moll Flanders” (1722). A naturalist before his time, Defoe simply presents his all-too-human heroine, reserving judgment and even seeming to approve as she goes about her mercantile business of being a whore, thief and wife. Moll concerns herself with the minutiae of her finances in a way almost unprecedented in serious literature: She worries about whether to put her money in a bank, wishes she had a financial advisor, haggles over the prices of her stolen goods and is constantly counting up her worth. “Moll Flanders” is one of the first works to reveal the pathos and fatality of numbers: The guineas in Moll’s purse play the role formerly taken by God, or Fate. And Defoe relates it all with an amoral gusto that is disturbingly modern.

But money need not appear onstage to call the shots — as witness Jane Austen’s “Pride and Prejudice” (1813). Austen’s masterpiece is one of the most money-driven novels ever written. The fact that the subject is treated with such discretion only increases our happy awareness that large bags of loot are stashed under the floorboards. “It is a truth universally acknowledged, that a single man in possession of a good fortune, must be in want of a wife.” Austen’s bantering opening introduces the economic element from the outset. Elizabeth Bennet and her sisters are respectable, but not rich, and Darcy is loaded: “10,000 pounds a year” is a mantra repeated through the novel. And there is no other way for Elizabeth to maintain even her modest place in the world, except by marrying “wisely.”

Economic fatality and emotional need dance an intricate minuet: Should Elizabeth marry the repulsive Mr. Collins, thus ensuring herself a middle-class existence, or follow the dictates of her heart and hold out? She holds out and, of course, wins the proud Darcy, who takes his place as one of the first in the grand tradition of wish-fulfilling heroes in women’s novels — dark, dangerous and, by the way, rich men who turn out to be paragons of every excellence. The reader, and Elizabeth, get to have their self-righteous cake and eat their 10,000 pounds too. Elizabeth is a model of integrity, but she gets the rich man anyway and his yummy estate, Pemberley. (Austen, however, is too honest a writer to remain completely silent on the allure of wealth. It is a mark of her emancipated modernity that she allows Elizabeth, after she has viewed the rolling lawns of Pemberley, to muse, “At that moment she felt, that to be mistress of Pemberley might be something!”) “Pride and Prejudice” balances love and money as perfectly as any novel has ever done. It is the romantic middle-class utopia of cash, love paid in advance, no monthly payments.

But there is another side of the coin, and its ugly face peers out in the marriage of Elizabeth’s best friend, Charlotte, to Mr. Collins. When writers as discreetly well-bred as Jane Austen don’t say something, the silence is instructive — and she is completely silent about the future prospects of the “happy” pair. “Charlotte herself was tolerably composed,” Austen observes, placing herself in Charlotte’s mind after their engagement is announced. “She had gained her point, and had time to consider of it. Her reflections were in general satisfactory. Mr. Collins to be sure was neither sensible nor agreeable; his society was irksome, and his attachment to her must be imaginary. Still he would be her husband.” And this attitude, which cannot be said to be exactly euphoric, represents Charlotte’s romantic high point. Her later reflections seem less “satisfactory.” Such is the fate of a plain woman of small fortune in 1800 who has chosen “the pleasantest preservation from want,” marriage to an imbecile. The wolf of poverty can be seen baring his fangs before genteelly retreating beneath the tea-cozy.

For all her psychological modernity, however, in her decorum Austen seems to belong more to the 18th century than the 19th. She represents a last, pleasant escape from the new reality: Money has entered the building, but it is still possible to keep knitting. After her, however, comes the deluge. The modern view of money — ironic, obsessive, eroticized, moving from the most austere rejection to the most cackling covetousness — takes center stage in the great novels of the 19th and early 20th centuries, the works of Balzac, Dickens, Stendhal, James, Doestoevski, Wharton and the rest.

Money had far more power, more meaning, in the 19th century than it ever had before — or would after. The novel is the middle-class art form par excellence, and the 19th century is the golden age of the novel because the middle class is in its most dynamic, dangerous and mobile phase — its adolescence. Money is as unknown and talismanic in the novels of Balzac — whose lust for power of all kinds is deliriously palpable — as it ever was, or would be. In Balzac’s world, money still possesses an aura of magic; you can use it to change your deepest identity, without — as would now be the case — revealing that identity to be a void. Dostoevski’s novels, more schizoid than Balzac’s or anyone else’s, are torn between opposite urges: The gambler’s wild, half-crazy passion for money is thrown up against an equally intense, equally doomed spirituality. In “The Idiot,” the self-hating courtesan Nastasya Filipovna throws a bundle of 100,000 rubles into the fire and urges her money-grubbing suitor Ganya to pull it out with his fingers, as the tortured, asexual saint Prince Myshkin looks on — and Dostoevski is all of them.

It is not surprising that the 19th century also inaugurates the great literature of crime. Crime is the ultimate short-circuiting of a system that is already out of control. Fascinated and repelled by wealth, writers like Balzac, Dickens, Dostoevski and Poe were equally fascinated by criminals, by those individuals who had truly made wealth their God and their Devil. Dostoevski’s account of Raskolnikoff’s hideously philosophical murder in “Crime and Punishment” — is the life of the vile old pawnbroker worth the money he will get from her? — remains the most intense confrontation of Christian and existential values ever written.

With the advent of naturalism, that science-obsessed, ashcan-digging school of bitter truths, and the simultaneous death throes of class, money lost its strangeness, its aura. It would be gilded one last time in perhaps the greatest novel ever written about money, Fitzgerald’s “The Great Gatsby,” but its mystery was gone. Naturalism stripped money of its fetishized allure, revealing it to be an agent not just of hope but of defeat and destruction.

If “Pride and Prejudice” is the paradise of middle-class money wish-fulfillment, Theodore Dreiser’s “Sister Carrie” (1900) is its hell. It is a novel of almost cosmic entropy: Its characters move hopelessly on like cheap windup toys, buffeted by events they do not comprehend, their little wheels turning slower and slower until, one day, they fall over, kick a few times and lie still. Money alone can briefly stave off this fate, but money doesn’t come when it is called any more than Godot does. Carrie, Dreiser’s tabula rasa “heroine,” stumbles upon money by the merest chance; her success, rather than lightening the prevailing gloom, only makes it darker.

In Dreiser’s America, the system breaks people — and the worst of it is, it isn’t even a system, it’s just life. He is the miserable poet of capitalism’s nightmares, forever enacting the decaying events that happen after an evil “what-if”: What if you were born into the MacDonald’s hamburger-flipping class? What if that day you met the guy who gave you that big break your car had broken down? What if you were born in the wrong place? What if your life wasn’t charmed?

No writer has described the soul-shriveling experience of looking for work better than Dreiser. In “Sister Carrie” there are never any jobs, or somebody mean is looking out the window at you, or your feet are wet. Carrie’s husband, the doomed and listless Hurstwood, shuffles endlessly through teeming streets, too afraid to go into factories. He goes in and is rejected. Then he goes home. Then his money starts to run out. Then he goes back on the streets again. Then he goes home again. You keep waiting for the fairy godmother — don’t novels always have fairy godmothers? — but she doesn’t appear. A countdown begins: Hurstwood’s money goes down, down, by an easy and natural process, like falling asleep or getting older. Then he has no money at all. Then, by an easy and natural process, he loses his house. Then he is on the streets. His final act of will, his tiny rebellion against the easy, natural declining process of his life, is to kill himself.

For Dreiser, money is worse than malevolent — it is indifferent. With “Sister Carrie,” money becomes absurd: It has nothing to do with man. It may be the darkest, least alluring portrayal of money in all literature.

Fitzgerald’s “The Great Gatsby” (1925) also shows what Dreiser calls the “impotence” of money. But it shows money’s other side as well. It is perhaps the most effervescent, champagne-fizzy vision of wealth ever realized in literature. It is the delicacy and fatality with which both visions are balanced that makes “The Great Gatsby” unique, and makes it literature’s most haunting study of money. Literature after “Gatsby,” in what Harold Bloom calls the “Chaotic Age,” deals with money in myriad fascinating ways, from Tom Wolfe’s hilarious and sharp-eyed enumeration of why a rich New Yorker needs $500,000 a year to get by in “The Bonfire of the Vanities” to Martin Amis’ pell-mell, onanistic wallow in “Money.” But no work captures money’s double nature, its sadness and allure, like “The Great Gatsby.”

Jay Gatsby sums up, for good and evil, the American vision of money. He is a self-created man, a parvenu whose big yellow car and big mansion and easy, golden style hide unsavory secrets. But what makes him a tragic figure is that he is an utter romantic, obsessed with a woman, Daisy, whose very laugh had money in it — a woman whose wealth, unlike his own, is unquestionable. Gatsby buys his mansion simply so that he can look at Daisy’s mansion across the water.

In the most obvious sense, Gatsby loses Daisy because he is an upstart: She rejects him — if her drifting, what Fitzgerald calls her great “carelessness,” can be said to add up to anything as clear as rejection — when her thuggish, rich husband, Tom, exposes his past. But in a deeper sense, he never had her. He has been pursuing a chimera. “The Great Gatsby” is about the delusiveness of memory — and its inescapability. The green light across the water that Gatsby stares at, the “orgiastic future,” never arrives.

You escape the past by living in the present — but the present is always escaping, too. Money is what “Gatsby’s” characters use to hold onto the present. “The Great Gatsby” is so subversive and complex a book because Fitzgerald is not merely a moralist preaching “money can’t buy happiness,” he is acutely alive to the lightness of money, its style, its swing, the infinite shadings and pleasures it paints and makes possible. The singular elegance of his style at once explores and evokes the elegance of money. The drunken, vulgar roisterers on Gatsby’s lawn are not the ones who communicate the happiness of money; neither is Gatsby himself, nor Tom, nor Daisy. That happiness is glimpsed in passing, always just ahead, around a corner. It is glimpsed, paradoxically, in sadness, in the “poor young clerks who loitered in front of windows until it was time for a solitary restaurant dinner — young clerks in the dusk, wasting the most poignant moments of night and life.” Happiness is knowing that you are sad, making friends with the poignancy of your life. Money, in “The Great Gatsby,” is always on the verge of bringing happiness. If one can hold to that twilight moment, then something of the real thing can appear.

The lesson of “Gatsby” is that money can buy an unencumbered present — but what happens when the present isn’t there? When “we beat on, boats against the current, borne back ceaselessly into the past”? It is a lesson that Aristotle had given a long time ago: Limitless desires create not happiness, but a void, an empty soul, a life like a deserted mansion. Limitless desires are not created by money, although they can be exacerbated by it — they arise from a flaw that Fitzgerald suggests may be too deep for us to ever mend it, though we can try. The golden sun, the dream of pure wealth and pure happiness, is always setting. The best we can do, rich or poor, is learn to live at dusk, to cling to the most precious moments of night and life before they pass.

This week, for roughly the millionth time, E.L. James’ romance-bondage trilogy “50 Shades” nabs the No. 1, 2 and 3 spots on the New York Times bestseller lists. We don’t get it either. Every page of that book, which famously began as “Twilight” fan fiction, elicits a sigh of confusion and weird secondary embarrassment. The question is: Who would read this? (The answer is: Apparently everyone.) It’s the same baffled, helpless feeling we get when we sort through stock photos on a daily basis. Stock photos – which have been the subject of recent outstanding Internet satire – are used by this site, and many others, to illustrate our flood of content. Many are plain and simple, but a good portion are flat-out mind-blowing. Why did anyone think that photo was a good idea? It only made sense to join these forces. And so, we present to you passages from the most head-scratching bestseller of our time, illustrated with the assistance of inexplicable stock photography.

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It’s the third week of the garbage strike and Athens has begun to smell. Bright-colored trash bags fill the curbs and alleyways, and we have learned to step over the rubbish and avoid the blocks that had become unnavigable. We know which stretches are particularly foul — a stretch along Mavili Square, or the entire top end of Monastiraki. Odos Athinas is a sea of trash, and Omonia is ghastly but we don’t go there anyway. May has gone from unseasonably cool to raging hot, and the garbage seems to be melting. In front of the museum it’s like yet another installation project. When I arrive each morning I want to wretch.

It’s just before dawn when Isabel puts the final page down on the fat stack of paper that sits on the rumpled bedspread, next to an overflowing crystal ashtray and a crumpled soft-pack of cigarettes. She’d tried Wellbutrin and Xanax; she’d used patches and gum. In the end, the only thing that made her quit smoking was being pregnant.

But then, after everything, she couldn’t help but start up again. At first it was just a single cigarette per day, or two. Then it became a few, and within months she was back to full-throttle. Over the past couple of years, she’s tried to quit a few times, but not seriously. She anticipates — she accepts — failure. Because she doesn’t want to quit, not really. She wants instead to try, and fail.

“Are we there yet?”

It’s a dreaded sentence. When it’s spoken by an anxious child from the back seat, it’s enough to make stressed-out parents wish they’d never taken a family vacation in the first place. And even if it’s delivered as a sing-songy punch line, from an impatient partner or spouse on a long road trip, it’s an irritating eye-roller of a joke.

So this Memorial Day weekend — the unofficial start of the summer vacation season, and therefore the summer fiction season — we asked two novelists to reclaim the sentence in a new and adult context. For our latest fiction project, there was only one simple rule: Each story had to include the line “Are we there yet?” in a fresh and surprising way.

Whatever interactive fiction is (and we’re still figuring that out) it suffers from all the problems of traditional fiction and then some. The vast majority of novels and short stories aren’t much good, but when a branching fiction — along the lines of the old “Choose Your Own Adventure” children’s books — fails to engage, the first impulse is to blame the form rather than the content. Let “Frankenstein,” just released by Inkle Studios and Profile Books, serve as a reproach to that reflex. The app is a creative, subtle and sensitive adaptation of Mary Shelley’s classic novella, and it has singlehandedly renewed this critic’s hopes for interactive fiction.