Forty years ago, in a world that has long since disappeared, a writer who was no longer exactly young—he was 35 and, by the standards of the day, five years past untrustworthy—published a startling little book called The Adventures of Mao on the Long March. It was fiction of the sort that even now makes the novel as a form feel like something delightfully and bewilderingly new, which is, if you put any stock in the meaning of words, what a novel is supposed to be. Frederic Tuten’s book was a peculiar, fragmentary thing: all jump-cut and pastiche and deadpan mimicry. It was about Mao, but via the rabbit hole of pop assemblage. Tuten spliced a straight history of the Long March with paragraphs and whole pages culled from Jack London, James Fenimore Cooper, Melville, Hawthorne, Ruskin and Wilde, and he folded in parodies of Malamud, Faulkner and Hemingway ("You knew that if you said it all truly there would be enough there for a long time. Enough of the olives and Baked Alaska when the air conditioner blew at you hard in the fine little room behind the zinc of the bar at Sardi’s"). Mao discourses on art and poetry and "sex-love." He talks about Godard and Dalí and Wallace Stevens. Greta Garbo seduces him from atop a flower-strewn tank: "Mao, I have been bad in Moscow and wicked in Paris…but I have never met a MAN whom I could love."

Today, with all the indolent advantages of hindsight, we might file away Tuten’s first novel on that high shelf of heady oddities labeled "the postmodern," alongside the fiction of Robert Coover, Donald Barthelme and Gilbert Sorrentino, and perhaps a soundtrack of early Brian Eno. But in 1971 The Adventures of Mao on the Long March was no curio. Roy Lichtenstein designed the cover image: a smiling, stippled Chairman in a cartoon burst of color. (Warhol wouldn’t get to Mao for two more years.) Susan Sontag blurbed the book as "violently hilarious." Dame Iris Murdoch recognized Tuten as "serious." John Updike reviewed the book in The New Yorker. "We are confronted," he wrote approvingly, "with something truly other than the reasonable liberalism and sentimental romanticism that have shaped our radically imperfect world." That world would quickly fade into another, and then another, each more imperfect than the last. As for the "truly other," it would soon be exiled—if not from the culture entirely, at least from the local literary mainstream, a creek that would grow narrower as the decades passed, and less welcoming of the novel.

Tuten would not publish another book for seventeen years. The Adventures of Mao on the Long March fell out of print and became a strange, secret treasure, one whispered of by writers in the know. For years, it was easier to find in French than in English—Raymond Queneau was an admirer, and Les Aventures de Mao pendant la longue marche is still in the Gallimard catalog. But it grew alien with age. Mao had been an intensely optimistic work, written, in Tuten’s words, when China’s revolution was "still fresh and seemingly uncorrupted." Formally, it was not so much a rebellion against the inherited strictures of literary realism but a celebration in their absence, a gentle roast turned all-night dance party. By the time Tuten’s next novel, Tallien: A Brief Romance, was published in 1988, the insurrectionary playfulness epitomized by Mao had long since gone stiff. In the first world, at least—if we can allow ourselves the nostalgia of that term—postrevolutionary ecstasy had been poisoned by kitsch, commerce and too much bad faith. Mao had become an artifact.

Tuten would write of his first book, "I was taken by the idea of an impersonal fiction, one whose personality was the novel’s and not apparently that of its author, an ironic work impervious to irony, its tone a matte gun-metal gray with just a flash of color here and there to warm the reader." Tallien is warmer and more personal, if less brash and less bold: a sad, sober book, a stubborn ode to disillusion. It takes the form of a story told by a son to his late father, who, like Tuten’s own, had been a Southern gentleman turned radical labor organizer and who, like Tuten’s father, had left his wife and only son in the Bronx when the boy was still a child. When the novel opens, the father, Rex—a name that will reappear in Tuten’s work—has just died alone in Jersey City. The narrator wishes he could have told him about the life of the French revolutionary Jean Lambert Tallien. He can’t—so he tells us.

It is not a happy tale. One of the few Jacobin leaders to live through the Terror he helped spawn, Tallien spared the life of a count’s daughter, then fell in love with her. She would ultimately betray him, as he would betray his comrades and his principles alike before dying alone—"the fireplace cold, embers in the grate like the ashes of dead stars"—in a France once again ruled by a Bourbon king. Tallien’s is the story of utopia’s defeat, of the New Day’s devolution into a "post-revolutionary state parceled out among flunkies and underlings and bureauristocrats with ci-devant disco shades." The novel is at once a son’s melancholic revenge on his absent lefty father—marching the Kronstadt corpses past the silent old Bolshevik believer—and his acknowledgment of defeat before the old man’s untouchable integrity. The dead win every time.

If Tuten’s next and best-known novel, Tintin in the New World, feels in its frolicking elegiac irony closer to the world of The Adventures of Mao on the Long March than to Tallien‘s Reagan-era blues, it’s because much of the book actually predates its predecessor. An early draft opened with an invented letter from Mao to André Malraux. But it took Tuten twenty years to finish the book, and Mao and Malraux had disappeared from its pages by the time it was published in 1993. Not one to forget a kindness, in his dedication to his friend Hergé, creator of the sexless and eternally youthful cartoon adventurer, Tuten included a line thanking the Guggenheim Foundation for a grant awarded in 1973.

Like most of Tuten’s novels, Tintin in the New World half-follows Flann O’Brien’s half-joking dictum that the "entire corpus of existing literature should be regarded as a limbo from which discerning authors could draw their characters as required." Tintin, restless after a long year at Marlinspike with his faithful dog Snowy and old drunk Captain Haddock, sets off for Machu Picchu and there meets the assembled cast of Thomas Mann’s Magic Mountain, only slightly modified: the Jesuit fascist sympathizer Naptha (Naphta in Mann’s original), Settembrini the humanist, the beautiful Madame Chauchat ("whose voice purred of autumn leaves rasping across a grate") and her lover, the sensualist Peeperkorn. There are also characters of Tuten’s invention: a mysterious "Chinaman," the outlaw Pimento and Lieutenant dos Amantes, who tells of an Incan legend of a golden-haired god who will appear one day from the west to unite the oppressed indigenous peoples of the Americas: "Some say this new god is a man; some, a woman; some androgynous."

You may have guessed the end already, but before Tintin becomes a revolutionary jaguar messiah, he must grow into a man. The utopian spark survives, but wizened. Tintin learns of moral failure; of ambiguity, age, sadness, loss. He is introduced by Madame Chauchat to Mao’s old sex-love, now rendered hotly hyphenless: "to sexlove and sexkiss and sexsigh and sexbreath to sex longings and sex spendings, and more." Tuten lets the pair grow old at Marlinspike, then—"Thundering figs!"—rescues them from that dull dream of domesticity, turning back time and tossing Tintin back into the new world to adventure again.

Tintin is more gentle than The Adventures of Mao on the Long March or Tallien and easily Tuten’s funniest novel. In its reception, it must have felt for a moment like Mao redux. Roy Lichtenstein again painted the cover image (Tintin in an easy chair, a Matisse on the wall behind him and a dagger flying past). Susan Sontag wrote another blurb. Edmund White gushed in the New York Times. Another generation of novelists would discover the lush, off-kilter whimsy of Tuten’s prose—an encomium Paul La Farge wrote for The Believer would be added as an introduction to later editions—but Tintin in the New World seemed out of place. It was brilliant but had arrived at once too early and too late, its gravity too flip for the age of Clinton and Cobain, its irony too warmblooded for the Seinfeld crowd.

Tuten would publish two more novels over the next nine years. In 1997 there was Van Gogh’s Bad Café, in which the artist’s morphine addict lover walks through a wall in Auvers-sur-Oise and emerges in a not-yet gentrified East Village; and in 2002 The Green Hour, about a doomed, lifelong romance between an art historian and a peripatetic idealist named Rex. Both are soft, painterly books about love, art and death, written from atop "a mountain-high pyramid of the century’s murdered corpses," and bearing all the high humanist mournfulness that such a perch implies. Both are more concerned with the order imposed within the four edges of a canvas—or, by extension, a novel—than with the various Rexes’ expired dreams of social harmony. Painters are everywhere on and in these books. Tuten writes about Goya, Gauguin and especially about the otherworldly formal order of Poussin. The cover of Tallien was a David Salle painting. Van Gogh’s Bad Café was illustrated by Tuten’s friend Eric Fischl.

On the jacket of Self Portraits: Fictions, Tuten’s new collection of short stories, there’s a Lichtenstein again. It’s Portrait, an empty suit with a slab of holey yellow Swiss floating where the head should be. The painting is a nod to the Surrealists, which makes it a compound nod from Tuten: to his late friend Lichtenstein; to "such artists like Max Earnest and Salvador Dolly," as he has one character put it; to his own Mao and Tintin; and to the empty-suitedness of us all, our heads filled with holes and moldy cream, our lives imagined, dreamlike, almost gone.

While crafting Mao, Tuten later wrote, he was eager to avoid the favored material of first novelists: "the common tissue of fictionalized autobiography." The stories of Self Portraits, though, feature a very Tuten-like narrator, and several travel back to the penurious Bronx of Tuten’s childhood. (His mother and grandmother loom larger here than old Rex the wanderer, with whom he has perhaps made peace.) But the prose is too exquisite for there to be anything common about the tissue from which he crafted Self Portraits. Tuten writes with a calm, deft simplicity that leaves room for startling metaphor ("beneath a toothless sky," or "with a smile to kill a ripe eel") and for passages of fluid, melancholy beauty. The stories are concerned less with fictionalizing the past than with the fiction of the past, with the crucial play of fantasy through which we fashion ourselves, and with the limit of all such play: "What is so pressing," Tuten asks, "that makes Death so curt, so interruptive of the narrative?"

From story to story, settings and characters appear and reappear. The tables of a near-empty restaurant in a hotel across from Central Park. A missing waiter. An apartment facing Tompkins Square Park. A woman named Marie. A third man, sinister, shape-shifting, but always oddly familiar—the narrator’s unshakable rival. A pirate ship just out the window on Avenue B. A stylish young couple in love’s early blushes, "foolish and oblivious to the endings of anything, let alone to the end of love." Outside it is always snowing, except when it is raining or the world is on fire. Everything is beautiful and just out of reach, and everything will soon vanish.

Self Portraits is an old man’s backward glance on life, but it is not cynical, jaded or mean. It is vital, wistful and filled with sweet ache, with loneliness and longing and the manifold pleasures thereof. The narrator counts the things he will miss if only he could be around to miss them: birds, clouds, paintings, making love, every star. Art, he suggests, "is an inventory of missing." Love, the imagination and desire—these are of a single piece. They dwell on absence, the perishable, on what escapes our grasp. The narrator sits with Marie in the empty cafe. She’s leaving him. He can visit her sometimes, she says. Once, long ago and far away, he recalls, "we saw God in the weld of sea and sky." But he’s old and wise enough to know, and to ask, "what then would it change, seeing God?"

For all its gravity, Self Portraits is also terrifically funny. Tuten writes with enviable mastery. Who else could get away with beginning a story, "The sardines were not forthcoming," without sounding like a wiseass? Instead of sardines, the protagonist and his wife (not Marie but the toothy rich woman the narrator married instead) are served bowls of olives and squirming hirsute worms that have "childish red lips." Dalí and Buñuel are in the air, so another waiter in another story brings "a platter of sliced eyeballs," each one "plucked from the forehead of a baby Cyclops, so hard to find these days of Homeric disenchantment." In "Self Portrait With Circus," the narrator wants Marie all to himself at dinner. But she won’t go out unless he asks Eddie, "the bitter midget," to accompany them, and if he invites Eddie, he knows he’ll also have to invite the elephants—"you know how jealous they get"—and if the elephants come, he’ll have to ask the lions too, and the dancing snakes, and there’s no shaking Mario the strongman.

Self Portraits is a rich, gorgeous, almost perfect collection. It is a book about endings, published at a moment when we appear to have reached the end of something. The empire is crumbling and with it the brittle optimism that for decades kept at bay the fundamental, tragic transience of life upon which Tuten eloquently insists. In his darkest, most apocalyptic story, "The Park on Fire," the narrator wanders around Central Park as fighter planes pass over the city. Gangs of children march with "naked banners soaked in blood." A García Lorca–like poet has been beaten and left to die. The fascists have won, or is it the fundamentalists? It’s not clear, except that the winners don’t like books or art or unwed lovers. "Park on Fire" would seem too easy and familiar a humanist lament, except that none of it is simply literal and all of it hurts: "Everywhere everything we had ever learned was burning, everywhere everything we had remembered or would remember was burning, everywhere everything we were and had dreamed of becoming was burning." There’s no bright consolation here, just noble example. Tuten contemplates the loss of everything—not just the circumscribed details of his life but the whole universe in which he loved. He leaves the door open behind him and walks away with a sad chuckle, a knowing wink, a song.