At the press preview for Jeff Koons: A Retrospective, more than one member of the Whitney Museum’s curatorial staff urged visitors to dispense with “preconceived notions” about Koons and embrace the exhibition as an opportunity to view the artist’s perhaps too-well-known oeuvre with fresh eyes. One of the largest retrospectives the Whitney has ever mounted, Jeff Koons sprawls across three floors in ascending chronological order, lucidly mapping the artist’s career as he progressed from wunderkind art-school grad, to cultural provocateur, to the Mylar man we have known and either loved or hated for past twenty-odd years.

Those who revile Koons often do so on the basis of his later works, like Balloon Dog (or, more recently, Balloon Venus of Willendorf), the production and sale values of which have soared while their meaning has seemingly become ever more surface-deep. Admirers, meanwhile, employ a modernist-inflected rhetoric of materiality and monumentality to elevate this work on much of the same bases. Wall text at the Whitney describes how Cat in a Cradle required Koons to push the limits of a worldwide network of specialist plastic fabricators, suggesting that the work owes the “sense of wonder” it supposedly inspires to this insistence on medium and scale. On similar grounds, New York Times reviewer Roberta Smith hails Play-Doh (1994–2014), a towering mound of brightly colored globs that uncannily resemble the matte tackiness of the titular children’s putty, as an “almost certain masterpiece.” Those who agree with such a statement will be delighted by the playground of huge, shiny, pneumatic-looking things that is the Whitney’s top floor. Those inclined to see Play-Doh as little more than a colossal waste of time and money may find a surprising protagonist two floors down: Koons circa 1985. Believe it or not, Koons’ artistic practice was once pointedly critical and anything but insular. Jeff Koons: A Retrospective is most interesting (and encouraging) when it reminds us of this.

Of Koons’ earlier works, One Ball Equilibrium Tank, a basketball miraculously suspended in a tank of water, has certainly become the most iconic in the modern sense: The image has circulated so widely, little of its original meaning remains intact. Abstracted from its original context, the work may read as a prefiguration of the artist’s later obsessions with curvaceous form and the pursuit of perfection. (He reportedly recruited a Nobel Prize-winning scientist to determine the water salinity necessary to suspend the ball at the tank’s exact midpoint without it rising or sinking.) Such a reading would be accurate but woefully incomplete, for the work’s meaning is in fact inextricable from the other pieces that Koons exhibited along with it, many of which are assembled in the retrospective.

For one, the Equilibrium exhibition of 1985—Koons’ first solo show—included a series of unaltered Nike posters that humorously present famous basketball players in the garb of more conventionally respectable professions: Darrell Griffith becomes “Dr. Dunkenstein” by donning a white lab coat; a team dressed in dark suits gathers at a long courtside table dubbed “The Board Room.” Picking up on the predatory nature of the ads, Koons intelligently identified these figures as “sirens” promising an alternative form of social mobility to a mostly African American consumer base whose actual mobility was far from buoyant. Giving macabre form to this inference is a series of painstakingly detailed sculptures of floatation devices, such as a lifeboat and a scuba vest, ironically cast in bronze. Though they seem to offer salvation, they would in fact sink the user like a stone. The iconic Equilibrium Tank thus reveals itself as integral to a concerted critique of racially driven aspirational marketing. As such, it resonates as poignantly in today’s milieu of data mining and social-media-fueled ad targeting as it did in the Reagan era.

Social critique was more than a passing interest for Koons. In his Luxury and Degradation series, next on display at the Whitney, high-end liquor advertisements printed on canvas accompany sets of barware alluringly cast in stainless steel—what Koons referred to as “proletarian platinum”—to lay bare the class-based manipulations in alcohol advertising. Even Koons’ increasingly extravagant work of the late 1980s, by which point the artist had seemed to embrace a startling relativism (“…everybody’s cultural history is perfect, it can’t be anything other than what it is—absolute perfection”), can be seen as a continuation of this interrogative strain. One could even argue that Koons’ culture criticism reached its apex with his landmark Banality series, which presented kitsch, knickknack-style objects like Michael Jackson and Bubbles at an anthropomorphic scale, and his notorious Made in Heaven series, which frankly depicted the artist having sex with then-girlfriend Ilona Staller (aka La Cicciolina) at her pornography studio. Just as Equilibrium Tank was not merely a transcendental meditation on the embryonic, so these series may not be merely an “affirmation” of low culture. By boldly leveraging his art-world celebrity status to transform the kitsch and the pornographic into coveted art objects—a risky move that nearly ruined his career—Koons forced bourgeois viewers and buyers to reckon with their own “taste,” exposing the construct as a fundamentally oppressive instrument designed to induce shame and reinforce social divisions.

None of Koons’ work from 1994 onward has presented anything remotely as challenging. It is a pity that the Whitney stacks its cards the way it does, allocating an entire floor—its largest one—to this slick, repetitive lot and presenting it within a plainly valorizing, less-than-enlightening discourse about Koons’ meticulous attention to form, materials, and surface. It is clear enough how the mystique of the levitating basketball evolved throughout this artist’s career into the mountain of Play-Doh we now see before us. It is less evident what happened to the critical posture in which Equilibrium Tank was embedded. That is the question for anyone looking to jostle their “preconceived notions” about this peculiarly American artist. Whatever the cause of this loss, it arrived all too soon.

Jeff Koons: A Retrospective runs through October 19 at the Whitney Museum of American Art.