What first comes to mind when I think of Jeff Koons isn’t his art—not even his most memorable works, such as the stainless steel Rabbit of 1986 or the vast, flowery Puppy of 1992—but rather a cameo he had in a movie. In Gus Van Sant’s 2008 biopic Milk, Koons briefly graced the big screen in the role of Art Agnos, the progressive politician (and future mayor of San Francisco) who defeated Harvey Milk in the 1976 Democratic primary for a position in the California State Assembly. After a debate, Agnos offers his opponent a bit of advice: relentless criticism of the status quo isn’t enough to win the public over. Unless you can offer constructive programs to improve people’s lives, you’re just a downer, Agnos says: “You gotta to give ‘em a reason for optimism.” People need hope.

While the admonition seems to be faithful to the exchange reported by Milk’s biographer Randy Shilts, it might easily have been Koons’s own motto. When he began to attract attention in the early 1980s, the new watchword for art was “critique”; every up-to-date young artist was poring over books like The Anti-Aesthetic: Essays on Postmodern Culture (1983), edited by Hal Foster. Koons was one of the few artists of the time who wasn’t explicitly “anti” anything (except, as he has said, “anti-judgment”). What Foster called “a postmodernism of resistance”—one that “seeks to question rather than exploit cultural codes,” as he put it—was, for Koons, completely beside the point. Indeed, the catalog of the current Koons retrospective at the Whitney Museum of American Art features an illuminating essay, by the art historian Pamela M. Lee, about Koons’s “increasingly post-critical stance.”

Relentless optimism has taken him far, and the Whitney has chosen to glorify it by making the Koons retrospective the largest exhibition it has ever devoted to a single artist as well as the swan song at its much-beloved Marcel Breuer building on Manhattan’s Upper East Side, which has been its home for nearly five decades. Once the exhibition ends on October 19, the museum will have a hiatus until it opens its grand new quarters downtown in the meatpacking district sometime next year. (After the Whitney, the show travels to the Centre Pompidou in Paris and the Guggenheim Museum Bilbao.)

As Koons would later emphasize with series titles like “Easyfun” and “Celebration,” his art presents itself as one of affirmation, perhaps of a regression to childhood innocence, despite the knowingly creepy overtones that often lurk around its edges. Koons contends that his embrace of kitsch means a liberation from invidious standards of cultural distinction: “I was just trying to say that whatever you respond to is perfect, that your history and your own cultural background are perfect.” Here, Koons turns art’s precious promesse du bonheur into a New Age mantra of blissful idiocy.

Despite his powers as an artist, or rather as a sculptor (nothing Koons has produced in the guise of painting is of more than trifling interest), the work failed me. The survey of his message of hope left me feeling hopeless. I’m just not good enough at being the disinterested viewer to find myself cheered by a cheerleader for the neoliberal economy, no matter how brilliantly inventive. Scott Rothkopf, the curator of the exhibition, points out that the first review of Koons’s work had already pegged it as “a commentary on the glamour of conspicuous consumption.” This is what separates Koons from Warhol, who, in an era when CEOs made about twenty times the average worker’s salary (rather than nearly 300 times, as today), saw consumerism as a force that leveled social distinctions. “The richest consumers buy essentially the same things as the poorest,” he said. “You can be watching TV and see Coca-Cola, and you know that the President drinks Coke, Liz Taylor drinks Coke, and just think, you can drink Coke, too. A Coke is a Coke and no amount of money can get you a better Coke than the one the bum on the corner is drinking.” Koons, by contrast, has perfected the art of taking the same crap on offer at a big-box store—be it an ordinary pail or kitschy figurines—and making it better than anything you could ever own, so that the buyers of his art might feel superior to the plebs without having better taste than they do. “True, this might be possible only in an era of increasing inequality,” Rothkopf admits—but forget it, just enjoy, have a slice of gilded cake.

Besides, Rothkopf argues, Koons should not be seen merely as a huckster serving up his patrons whatever it takes to make a buck. Which, of course, is true: he couldn’t represent their values so convincingly if he didn’t share them. It’s not economic rationality that collectors find inspiring in Koons’s work, or in any of their other true favorites; it’s the perverse romance of business as the visionary pursuit of market dominance. Rothkopf reminds us that Koons has sometimes had to sell his pieces for less than what it cost to make them—“His business model has always been risky at best and disastrous at worst”—and argues that this sets him apart from such other market darlings as Richard Prince, Damien Hirst and Takashi Murakami. But the same thing is true for all of them, even Prince, who is a more traditional kind of artist: they put the market at the service of their obsessions. Murakami, reminded by the journalist Sarah Thornton of Warhol’s maxim that “Making money is art…and good business is the best art,” just laughed and said, “That is a fantasy!” Jeff Bezos knows you don’t have to show a profit to get rich, and Donald Trump knows what it’s like to face bankruptcy; in today’s economy, “risky at best and disastrous at worst” is just how things are done. In the end, it’s always the others who pay. Modern-day moguls have learned to think of themselves not as canny bean-counters, the organization men of yore, but as titanic creative geniuses in the Romantic mold of a Wagner or Rodin; they expect of an artist no less. It’s entirely characteristic of Rothkopf’s Marie Antoinette attitude that, even as he invites the museumgoer to admire the spirit of risk that led Koons to “lay off nearly his entire staff” in 1997, he has no thought to spare for the laid-off workers themselves.

Yet despite Rothkopf’s paeans, appalling as they are, to Koons’s open-eyed devotion to “the unifying sign of money” (somehow morally or intellectually or even aesthetically superior to the approach of other artists, whose work seems “to buckle with embarrassment under a pecuniary attention it neither seeks nor sustains”), I have to agree with his essay’s concluding point: colleagues recognize in Koons what they call a “real artist.” Of course, it’s almost impossible to know what vivid yet ungraspable intuition is embedded in anyone’s application of this honorific, but I suspect that in Koons’s case, it always has something to do with the intensity with which he pursues his work’s realization. But there are better ways of achieving this than by becoming the CEO of one’s own art brand. In previous columns, I have argued against the view—common among some cultural critics—that artists who are promoted by the market can for that very reason be taken as affirming in their work the values of their collectorship; as Rothkopf rightly says, “Any monochrome painting can be subject to an accelerating price index without visibly registering that fact.” But Koons really is an emblematic artist in this sense, and Rothkopf’s flippancy illustrates how handily the artist’s work exemplifies our reactionary times.

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But for those of us who aren’t inclined to swoon over Koons’s success at becoming the Steve Jobs of art, what’s left to appreciate? The great jumble of his retrospective doesn’t answer the question. While Koons’s cultural influence certainly justifies the full-scale, down-to-the-last-detail treatment, the retrospective shows that only his work from the 1980s has any real artistic consistency. What’s striking about that work, especially in view of what followed, is the flatness of its affect. It doesn’t try to excite the viewer, but rather to lure him or her into contemplating with a certain neutrality what otherwise might have been dismissed as beneath notice. Consider his sculptures consisting of vacuum cleaners encased in acrylic boxes; a somewhat alien, theatrical light is cast on them by their being lit from below by fluorescent tubes. It’s a very subtle effect. I can’t take very seriously the pseudo-Freudian hooey with which the artist has encouraged his commentators to surround these works—supposedly they conjure “sexual associations” both male and female with their “pliant trunks, sucking orifices, and bags that inflate and deflate like lungs” (though we never see these in operation). I defend to the death the right of any person to find erotic significance in a vacuum cleaner, but my own inclinations go otherwise. For me, these works take something utilitarian and turn it into a collectible; the vacuums sit untouched in their cases like investment-grade Barbie dolls that will never be played with but simply preserved in perpetuity in cryogenic splendor.

I can already hear the rejoinder: Isn’t that true of all art objects? Yes and no. There’s something more to art, something that doesn’t necessarily take the form of what the ’80s art world called “criticality” but that still refuses to lull the viewer into believing—as the art historian Alexander Nagel recalls when he first saw Koons’s work—that “I didn’t have to do anything other than accept it.” Religious icons, totalitarian propaganda and commercial advertising all might urge that—but icons, propaganda and advertising only become art when we no longer hear them whispering: Don’t think anymore, just give in.

In any case, subsequent works like those exhibited under the title “Luxury and Degradation” showed Koons’s investment in the collectible as a model for his art. These 1986 stainless-steel sculptures were cast from objects of display, such as bourbon bottles in the form of a train set (originally in porcelain); supposedly Koons had his steel replica filled, like the original, with whiskey at the distillery. Likewise, the accompanying liquor ads were not rephotographed, as an artist like Richard Prince would have done, but printed from the original plates with high-quality oil-based ink on canvas. Koons was an appropriator, like other artists of the time, but his point was always to make a better, more exclusive version of the found object—to borrow his terms, not a degraded version but a luxury one.

Though I have never loved Koons’s work, it was the sort of enterprise that made New York in the 1980s an artistically absorbing place. From show to show, one could see Koons pushing himself further, with the curious result that each show made the last one seem, in retrospect, almost classically composed. And never was that truer than with his 1989–91 “Made in Heaven” series, with its startlingly autobiographical turn for an artist who had previously touted the “objectivity” of the ready-made. In intimate detail, the series celebrated the artist’s sex life with Ilona Staller, or La Cicciolina, the Italian porn star and politician who was also, for a time, his wife. As it turned out, this intertwining of art and life was a disaster: the marriage ended in an acrimonious divorce and a bitter custody fight that was never resolved because an American court granted custody to Koons while the child was in Italy with Staller. One result was a hiatus in Koons’s work, after which he began a series whose title, “Celebration,” can only be seen as compensatory, and inadvertently ironic; his difficulty in finishing pieces to his own satisfaction can be detected in their dates of production, not uncommonly 1994–2000 or even 1994–2006. For Rothkopf, this is evidence of Koons’s devotion to perfection, but to me, it suggests the anxiety beneath the works’ shiny, happy surface. From here on out, in fact, Koons has thrown himself into an ecstasy of falsehood. His work blossoms, if that is the right word, into an ever more gargantuan effort to create, as if to confound the cool gaze solicited by his art of the 1980s: a visual frenzy of bright colors and clashing imagery on an ever-increasing scale and with ever-intensifying technical demands in manufacture, always more overbearing yet more ingratiating—art as an endless distraction from its own emptiness.

Not that the latter-day Koons is never any good. Play-Doh (1994–2014), the big pile of polychromed aluminum, is probably his best work since Puppy. Its evocation of tactility is extraordinary; its highly artificial color seems at once extremely accurate and completely abstract; and its fundamental dumbness is so funny that it’s clever. More often, however, the work’s intensity of realization is hardly matched by an intensity of conception. Perhaps the best illustration of this is not at the Whitney but outdoors at Rockefeller Center, where Koons attempts to reprise the success of Puppy—presented there in 2000—with a work from that same year, Split-Rocker—a thirty-seven-foot-high flowering topiary monument in the form of the mismatched left and right sides of two rocking horses, one of them a dinosaur rather than an equine. On this scale, and in this material, the image—on view at the Whitney in a much smaller polychromed aluminum version from 1999—loses focus, since the two sides are now insufficiently differentiated. In retrospect, it makes one wonder whether the success of Puppy was due to much more than the original choice of medium; it could be that flowering topiary will simply never be usable as an art medium again. And how bad would that be?

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Koons will likely have a place in art history, but it may be because of his influence more than his work. As evidence of that influence, consider the most talked-about piece seen in New York City this year, Kara Walker’s ironically titled A Subtlety, or the Marvelous Sugar Baby, which was presented by Creative Time in the late spring and early summer at the former Domino Sugar factory in Williamsburg, Brooklyn. This was a surprise turn for an artist who has not previously been known as a sculptor; Walker’s signature works have been grand-scale cut-paper tableaux, silhouettes depicting racially and sexually charged narratives uncomfortably mixing historical memory and perverse fantasy, always on the border of the unspeakable. Hers is not an art that says to anyone, “Your history and your own cultural background are perfect.” Walker prizes ambivalence. But like Koons’s Puppy, A Subtlety was made from an unusual material on a gargantuan scale to create a new kind of impermanent monument: a sphinx-like, blind-eyed “mammy” made of white sugar, thirty tons of it glazed over an armature of polystyrene foam. Surrounding it was a retinue of attendants made of candy and sugar.

Almost as strong as the sculpture’s visual presence was its scent. The place reeked of sugar, and the smell wasn’t sweet. It stank like some unpleasant kind of labor. The dank atmosphere of the abandoned factory was like that of a vast tomb. We all love sweetness, so we like to forget what it takes to make it. Sugar production in the New World was inevitably allied to slave labor—and, metaphorically, our dependence on sugar is another kind of slavery. “I wanted to do this,” Walker said, “because I wanted to have my fears challenged out of my body.” I recognized myself in those fears, and that unhappy knowledge was nonetheless pleasurable because it reminded me that I am bigger than my fears—when I can look at them. In that, Walker gave me more hope than a warehouse full of works by Koons.

And that’s despite the fact that A Subtlety, no less than Koons’s work, is a creature of capitalism—of the former Domino Sugar company, which donated the sugar, and of the real estate interests that will tear down the historic factory building and make a fortune from the gentrified future of Brooklyn. Walker’s art has always recognized the lure of complicity, but has never pretended anyone should be happy about it.