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William Makepeace Thackeray, one of the fathers of modern prose, possessed a wickedly ironic, savagely unsentimental tone that marks him as the opposite of his contemporary and great rival Charles Dickens. And he had a life so extraordinary, so marked by sudden twists and unexpected reversals, that it reads like something out of one of his many picaresque novels. Traversing multiple continents, winning and losing fortunes, falling in love and having his heart broken, Thackeray seems to have written directly from lived experience. The modernity of his works, however, particularly that of his masterpiece Vanity Fair, arises from their irony. We are always looking for the “real” Thackeray on the page, seeking certitude in his characters, and facing instead an enigma.

Born in Calcutta in 1811, he was the only child of a father who worked for the East India Company, during the height of colonial rule. Shipped home to England at the age of five when his father died, young William supposedly spied Napoleon on a ship along the way. His mother married an officer, a civil engineer whom she had loved before marrying his father, a plot the grown Thackeray would recycle many times. Introduced by his stepfather into the punishing world of English boarding schools, Thackeray later attended Cambridge and the Middle Temple, leaving both without taking a degree and traveling on the continent instead, where he supposedly met Johann Wolfgang von Goethe in Weimar. Thackeray inherited his biological father’s sizable fortune in 1832, but squandered it on gambling and investments in newspapers, the start-ups of the early 19th century.

Fleeing to Paris to study painting—he was a gifted caricaturist, and his drawings would later accompany his writings—Thackeray married Isabella Shawe, an Irishwoman with little family fortune. They would have three daughters, one dying in childbirth, and Isabella suffered increasing mental illness from the strain. She would die in an asylum. William became a de facto widower and man about town, seen at social clubs and doting on his daughters. He gradually fell deeply in love with Jane Brookfield, the wife of one of his best friends from Cambridge, another plot that would go into his books. He died unexpectedly at the age of 52, from an excess of “guttling and gorging.”

In other words, like countless dropouts and dilettantes before him, Thackeray had really been in training all along, learning how to become a writer. Like Charles MacArthur and Ben Hecht, the Chicago newspapermen who would go on to write The Front Page, Thackeray’s fiction bears the trace memories of his journalism. He seems to have been exposed to much of human vice and ugliness, and many indelible stories. Living during the golden age of the magazine and newsprint—an era of fake news and flim-flam, of ad hominem anonymous attacks, of con men, gamblers and financial speculators, of which he was all three—Thackeray wrote for many rags under a number of colorful pseudonyms, including “Mr. Michael Angelo Titmarsh,” “Fitz-Boodle,” “Ikey Solomons,” and “The Fat Contributor.” In works such as The Yellowplush Papers (1837)and The Luck of Barry Lyndon (1844, adapted by Stanley Kubrick into a 1975 film), he became a virtuosic juggler of incident and innuendo, speedily sketching in seedy characters while addressing the reader with a metafictional wink.

Vanity Fair was originally published in 19 serialized installments in Punch magazine between 1847 and 1848, much like a prestige TV show would be nowadays. Accompanied by Thackeray’s illustrations, it was subtitled “Pen and Pencil Sketches of English Society.” The first work Thackeray published under his own name, Vanity Fair helped to establish his fame and fortune, and much of his posthumous reputation now rests upon it.

The novel is a unique innovation on the Bildungsroman, the form popularized by Goethe’s Wilhelm Meister’s Apprenticeship (1795-6) and translated into English by Thomas Carlyle in 1824. Taking its name from Alexander von Humboldt’s term for the education of a self or cultivation of personality (Bildung), Goethe’s is the first example of a work in which the dramatic arc is not that of an adventure or a romance but of a person coming of age, in part through coming to understand their culture and society. In other words, without Wilhelm Meister, there is no Catcher in the Rye or Huckleberry Finn, no Portrait of the Artist as a Young Man or Their Eyes Were Watching God. No Boyhood or Ladybird.

Depending on how one classifies Jane Austen’s works, Thackeray’s is perhaps the first example of the femaleBildungsroman, a forerunner of Henry James’s Portrait of a Lady (also published as a serial, from 1880 to 1881). Always sensitive to the precarities of social identity, Thackeray writes with surprising acuity about what it means to be a woman in a patriarchal society. Though the working title for the book was “A Novel without a Hero,” Thackeray in fact offers us two: Rebecca (Becky) Sharp and her best friend Amelia Sedley. Part of the novel’s pleasure derives from toggling back and forth between their symmetrical narratives with ironically contrasting tonalities. Becky, having no family fortune, is determined to make her own way in the world, morality be damned, whereas Amelia the heiress has the relative privilege of affording more romantic airs.

The period is the British Regency, during the Napoleonic Wars of the 1820s. Over the course of the action, the titular wheel of fortune in the fair becomes a multivalent metaphor for each woman’s experience. As their reputations rise and fall, each seeks to find their place in the firmament. Thackeray intended Vanity Fair to “indicate that we are for the most part foolish and selfish people … all eager for vanities,” but in many ways he achieved the opposite, vividly dramatizing the roguish charm and eternal optimism of the human condition.

Kate Hamill, a prolific adaptor of Victorian fiction, focuses on female-oriented stories, offering an implicit corrective to the male-biased nature of the classical canon. She has found a new, delightfully non-stuffy way of translating them to the theatre by imagining them on a Shakespearean-style empty stage. In the case of Vanity Fair, Hamill brings Thackeray’s picaresque structure to life by theatricalizing his tendency to address the reader in that inimitable, moustache-twirling style. As in Thornton Wilder’s Our Town, a Stage Manager narrates the action and sets the scene. Characters jump into and out of the frame, while narration allows for wide landscapes and gaps in time to be traversed with ease. The effect allows for both sarcasm and sentimentality, zooming in on vivacious human scenes and striking a wry distance when necessary.

Beneath Hamill’s theatrical inventiveness and palpable joie de vivre, however, lies the seemingly inexhaustible mystery of Thackeray’s masterpiece. The wheel goes up, the wheel goes down, and we watch as each character plies their trade at the game of life. As the carousel makes its final spin, between virtue and vice, Thackeray and Hamill seem to be asking, with the same half-smile, which is right and which is wrong? And how much of our own class or gender determines the answer? The answer remains unclear. In this novel of cultivated sensibilities, the wheel of identity never stops turning.