Martin Kippenberger cultivated failure. The German artist’s life was littered with half-baked or misconceived projects soaked in self-indulgent irony. An unfinished series of black-and-white paintings marks the beginning of a career that would follow many paths towards a series of dead ends. Talented as he was, Kippenberger, who was 44 when he died in 1997, had little discipline and no follow-through. The retrospective of his work at New York’s Museum of Modern Art left me agog at all this squandered potential.

The show reflects the messiness of the artist’s career. At first, I couldn’t even figure out where the exhibition began. The door next to the introductory panel led to his late work: was I meant to follow his development Benjamin Button-style, backwards towards his beginnings? I asked a guard, who shrugged and pointed me in exactly the wrong direction. The few wall texts hardly explained what Kippenberger was after, except to point out the obvious: that he wallowed in excess.

Kippenberger’s mother died when he was 23, leaving him with a substantial inheritance and only the vaguest sense of purpose. He aspired to a career on the stage and went to Florence, of all places. Acting soon fell by the wayside but he never lost his appetite for self-display. An attention-seeking drunk, he faithfully indulged his whims, whether they involved sex, partying or art. And he was mean, painting with a satirist’s ruthlessness, if not always with perfect aim.

To appreciate his work requires a high level of you-had-to-be-there tolerance, since so much of it consists of inside jokes about the German art scene in the 1980s and 1990s. These attacks might have come clearer if MoMA had included some of his victims in the show; without that context, Kippenberger’s art devolves into a scattering of childish jabs.

That opening fanfare of black-and-white canvases is his riff on Gerhard Richter, the elder statesman of German art. Richter painted from photographs, elevating a roll of toilet paper, a snapshot portrait or a generic office block by drawing a translucent veil over the scene as if he were observing life’s banality through a philosophical screen. Kippenberger poked fun at the project by churning out an incoherent stream of fragments – a pig in an oven, the top half of a woman’s face, the hindquarters of a stone lion – executed with snide nonchalance. He had planned to produce a stack of pictures equal to his own height, but ran out steam.

Having gently dispatched Richter, his next – and most lasting – target was the angsty, self-important and well-remunerated German neo-expressionists, who were flying high as Kippenberger came of age. Anselm Kiefer, for instance, mixed straw and burlap with his oils, and Kippenberger mocked the crusty effect by slathering a real Ford Capri automobile (pictured) with an unappetising concoction of brown paint and oatmeal.

He was prone to icky provocations. What at first glance appears to be a semi-successful, quasi-cubist composition in the colours of the German flag gets a jolt of trenchancy from its title, “With the Best Will in the World, I Can’t See a Swastika”. The symbol is prohibited in Germany as a way to deny neo-Nazis an insignia to rally around, but Kippenberger was outraged by what he perceived as hypocrisy and censorship. For Germans to avert their gaze from the swastika was to suppress a legitimate historical reckoning. His response was to hint broadly at the forbidden form, like a child testing the boundaries of the permissible. He was called a fascist for his pains but the gambit was really more of a punk polemic than a political programme.

Kippenberger didn’t put forth a thoughtful critique so much as a collection of provocations. That hasn’t stopped his academic apologists from erecting flimsy theoretical scaffoldings around his work. In the show’s catalogue, the scholar Diedrich Diederichsen takes on “Three Houses with Slits”, a triptych depicting three modernist buildings: The Betty Ford Clinic, a Jewish elementary school and Stammheim, a German penitentiary notorious for holding members of the urban guerrilla Baader-Meinhof gang. The paintings are deliberately slapdash affairs that present conceptual challenges beyond the formal crudeness and careless brushwork. “It is not the buildings themselves that reveal something, which is what a superficial interpretation might suggest,” Diederichsen warns, before plunging into the murky depths: “Kippenberger has been able to create a basic allegory of the relationship between art and life as a political reality. Art can always depict the symbolic prisons, reveal their structural similarities (slits) which separate reality and life from talking-about-it and cut off life from discourse. Here art has to stitch them together.”

This exegesis only roils the waters. Did Kippenberger bracket these buildings together to imply that all three are forms of confinement? That modernist architecture is capable only of creating jails? That addicts, inmates and Jewish children belong in the same category? The kindest reading suggests that the artist is expressing sympathy for those who have been relegated to society’s margins, but any way you look at it, the grouping is casually incendiary.

The most winsome work at MoMA is a pair of surrealistic lampposts. One, “Street Lamp for Drunks”, undulates as if in sympathy with an unsteady boozer. The other runs like a thread in and out of the gallery wall. But even these sardonic gestures are complicated by contempt and loathing, for Kippenberger himself was one of those lamppost-leaning alcoholics, and he chronicled his dissolution in increasingly merciless self-portraits. I came away not shocked, not shaken or enlightened, but merely dismayed by a sensibility so pickled in acid. Much is made in the show of his puckish humour but in truth his grandest statements were acts of petty enmity – saturnine comments on artists more talented than he.

‘Martin Kippenberger: The Problem Perspective’ runs until May 11, tel: +1 212-708 9400; www.moma.org