The Christopher Wool retrospective at New York’s Guggenheim Museum

I would not like to be Christopher Wool. Even spending an evening with him might be more than I could take. Wandering through his mind at the current retrospective at New York’s Guggenheim Museum is like getting lost in a forest of anxiety. There’s not a flicker of joy in the show, just a tundra of bleak splodges, obsessive patterns, acid incantations, and anguished erasures. “I define myself in my work by reducing the things I don’t want,” Wool once said. “It seems impossible to know when to say ‘yes’ but I know what I can say ‘no’ to.”

“No” is a word he uses profligately, denying himself colour, figure, and solace. At times – as when he obscures an earlier work with whorls from a spray can – he seems to be shaking his head at the viewer too. But despite his negativity, the manically exuberant art market adores him. You might think that his work would resonate mostly within a small circle of the terminally depressed, yet it commands stratospheric prices. Last year an enamel-on-aluminium painting bearing the imprecation “Fool” sold at auction for £4.9m ($7.7m), which suggests that at least Wool must be suffering in comfort.

One of Wool’s afflictions, it seems, is doubt that the whole enterprise of making art is actually worthwhile. You can sense his instinctive need to express himself through paint, but he keeps tamping it down, using patterns to neutralise gestures, then bleaching out even those. At the heart of his work is a vibrating tension between passion and renunciation. You can see it in one of his more recent untitled works from 2012. A dark cloud bursts out from the centre, flinging droplets towards the edges of the frame, as if Wool had sloshed paint, Jackson Pollock-like, on to a canvas laid out on the floor. Only it’s not a painting at all, but a silkscreen, the product of mechanical reproduction. Rationalism asserts itself in the form of axes that divide the rectangle into quadrants and slice the spreading stain into two parts, one crimson, the other black, that don’t quite line up. The piece has an almost forensic quality; it could be the coldly observed evidence of some mysterious act of violence.

Wool studied with Abstract Expressionist painter Richard Pousette-Dart at Sarah Lawrence College in Yonkers, then at the New York Studio School, where the spirit of Hans Hoffman still hovered. That training nearly hobbled him at the beginning of his career in the late 1980s, when trend-tracking critics once again predicted the death of painting. Abstraction was deemed to be even farther gone; artist, editor and curator Thomas Lawson said it contained “the last manneristic twitches of modernism”.

Still, Wool squeezed a few drops of satisfaction out of the dried-up tradition by resorting to an old gambit: irony. He painted while intimating that he was doing nothing of the kind. Instead of handling a brush, he went to the hardware store and bought rubber rollers with wallpaper-like patterns incised in them, the kind that downmarket New York landlords use to give painted hallways a cheaply genteel feel. Wool covered enamel panels with repeating vines, tendrils and fleurs-de-lys. The result cleverly mingled Pollock’s all-over abstraction with Warhol’s taste for deadpan reiteration.

Wool’s battles with himself went far beyond an art-historical debate over abstraction. In 1987 he started on a multi-decade series in which he stencilled black block-cap words on to white paper. One of the first reads: “SELL THE HOUSE SELL THE CAR SELL THE KIDS.” In Francis Ford Coppola’s 1979 movie Apocalypse Now, a US soldier in Vietnam scrawls those desperate words to his wife before vanishing into the jungle. In Wool’s impersonal type, the text could be a political poster, a ransom demand or a suicide note. This piece too seems to belong in a police file.

Ominous, hard-to-parse texts became a recognisable element in Wool’s catalogue. With his penchant for denial, he began removing such non-essentials as the spaces between words, and that terse, pared-down quality buzzed with urgency. He mounted “THESHOWISOVER” on an urban billboard, issued the awful monosyllabic order “RUN,” and sucked the vowels out of “trouble” to make “TRBL”. These sign works have a creepy, horror-film quality, like “REDRUM” written in lipstick in The Shining.

Despite his devotion to “no”, Wool isn’t really content with subtraction. He builds his works into palimpsests, laboriously layering patterns, headlines, graffiti-like scrawls and ghoulish splatters, then silk-screening the whole thing on to linen, slathering it with thick strokes of obliterating paint, and finishing it with a smudge. It’s almost as if, whenever Wool has built up something too refined, he then feels the masochistic need to mess it up. He is a virtuoso of blemishes and scars.

Sometimes he switches weapons, ruthlessly pointing a camera at scenes of romantic grimness. A shopping cart, caught like a deer in the flash, hugs a graffiti-covered tiled wall. Black water oozes from a fire hydrant into the flooded gutter. The atmosphere is punk noir: violent but bleakly appealing. In one 1984 performance piece, Wool, a fan of Raymond Chandler, read a passage from The Simple Art of Murder that could be his motto: “It is not a fragrant world, but it is the world you live in, and certain writers with tough minds and a cool spirit of detachment can make very interesting and even amusing patterns out of it.”

The “amusing patterns” that worked their way into Wool’s paintings also appeared before his lens – in paving, signs, carpets, raindrops and patches of streetlamp glare. In a free-associative essay in the catalogue, Richard Prince calls the photographs “back-up” for the world according to Wool.

And as Prince hints, Wool works like an artist with something to prove, but that defensiveness proves tiresome in a retrospective of this scale. Curator Katherine Brinson has done a marvellous job of preventing overload. She intertwines the various strands of his career so that he seems for a while like a more versatile artist than he really is. But even she can’t lighten the bummer that he’s determined to inflict, or wave away the tedium of his obsessions. The thing about too much Wool is that eventually it starts to unravel.

The Guggenheim show is a record of cerebral struggles that were already dated by the start of his career. Roy Lichtenstein had long since turned the brushstroke into a frozen relic, Jenny Holzer had elevated slogans into art, Warhol had made something monumental out of the Rorschach blot, and punk rockers had made a fetish of trashed rooms and suspicious stains. Wool’s art doesn’t feel like a pastiche of references, but it does feel burdened and ambivalent, the work of someone who’s always looking over his shoulder, who’s tempted to follow his own command to run.

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‘Christopher Wool’, Guggenheim Museum, New York, to January 22 guggenheim.org