George Condo: The comedy of horror

Hip-hop legend has it that Kanye West hoped to make the cover of his last album so street-cool that it would at the very least offend, and at best, get banned.

To that end, he called on George Condo, an artist with a track record for dismantling cultural icons – God, Jesus and the Queen among them – with a dark, disfiguring comic savagery.

Condo did not disappoint, offering West a pick of startling images – a portrait of the singer with four sets of teeth, another with his head decapitated and impaled by a sword, and a lurid scene of a naked black man being straddled by a white phoenix-like creature. West went with the last image for the cover of My Beautiful Dark Twisted Fantasy and it was duly banned by certain American retailers whose sensibilities were offended by its graphic bestiality.

It was certainly not the first time Condo's work had unsettled. His oeuvre exudes a profound and compelling oddness that has sometimes been mistaken for attention-seeking profanity and insolence. Three decades after launching his career with a series of fake Old Masters that seemed to mock the artistic canon, he has combined European historical portraiture with American caricature to present old and modern-day heroes in an unheroic light.

His intelligence and iconoclasm has earned him a starry following: The Chapman Brothers, Fiona Rae and Glenn Brown; Salman Rushdie who created a character in Fury based on a Condo portrait; even the Olsen Twins and Patti Smith.

Two exhibitions next month will appraise Condo's achievements, and reflect on the popular misconception that he is merely sending-up his parade of tragic-comic subjects. The Hayward Gallery will showcase his most important portraits and sculptures in Mental States, which reflect his desire to explore the "outer suburbs of acceptability", while Sprueth Magers gallery will focus on his drawings.

Born in 1957 in New Hampshire, the artist moved to New York and quickly claimed a place in the thriving arts scene of the city in the 1980s, befriending Keith Haring and Basquiat, William Burroughs as well as the beat poets, Jack Kerouac among them. But while Haring and Basquiat were building a tradition of pop and street art, Condo went against the zeitgeist of the East Village arts scene to focus on the work of the Old Masters. After some time in New York, Condo left for Paris where he spent time absorbing the tradition of painting by pitching up at the Louvre for hours on end to copy the Raphaels. "It brought me back to painting," he said years later, "which wasn't fashionable at the time."

Ralph Rugoff, director of the Hayward Gallery and curator of this show, explains that the art-historical references in his work that have earned him a reputation as "the artist's artist" are part-reappraisal, part-homage, though they may on the face of it be read as a savage kind of comic replication. Condo developed a quirky line of "fake Old Master" portraits that combined stylistic elements borrowed from several different artists, including Velázquez, Rembrandt and Goya.

One such work is called Memories of Rembrandt, based on a self-portrait by the artist in 1668, but is barely recognisable for its scrambled features. Another canvas called Memories of Picasso, which was completed in Paris after he began an exploration of the Spanish artist's work, also has a Cubist jumble of a face. He painted several pieces featuring Picasso-esque fractured anatomies and double-eyed profiles, but this face looks as it it has been "flayed open", says Rugoff, such is its ghoulishness.

In the 1990s, he developed a freakish kind of pictorial species that he labelled "antipodes", pin-headed beings that summed up the different, sometimes unnameable states of human consciousness. They appeared to be less human, more a manifestation of complicated emotional registers, some demented, others manic in their postures. What differentiated them from straightforward caricature was the pathos and vitality they carried alongside their internal horrors.

Condo has suggested in past interviews that he seeks to capture a kind of psychological Cubism, an expression that "goes between a scream and a smile.... that reflects simultaneous emotions or conversations with the conflicting voices in your head".

Controversially, he began drawing on religious figures using these "antipodes" – a 2002 portrait of Jesus shows him boggle-eyed and shabby, like a "refugee from a rehab clinic for steroid abusers", reflects Rugoff. "Above the puckered topography of his bulbous nose and cheeks, a pair of vertical eyes convey a look of cartoon alarm, as if he were not quite sure how he landed in this catastrophe of a face." There is also a kitschy portrait of God, his arms in spread open on an invisible cross, surrounded by a cloud of celestial light, which appears deliberately tawdry and cartoonish.

When in 2006, he was commissioned to produce a portrait of Queen Elizabeth to hang at Tate Modern, he ended up making a series of 10, because of his belief that a single portrait cannot hope to capture the totality of a person. They were given arch titles (Blonde Queen, Metaphysical Queen, Comic Queen, Pop Queen, The Mad Queen) and showed her face in incarnations ranging from demure to garish, surreal and sinister, with over-blown cheeks, carrots in her ears, and the large red rictus-grin of a circus clown.

The series sparked a Daily Mail outcry, which charged Condo of portraying the head of state as a "toothless Cabbage Patch doll". In his defence, he claimed that his work "has the ability to make you smile, which she [the Queen] seems to have in real life".

Rugoff explains that Condo's task is more nuanced than an exercise in punkish irreverence: "It's not just a sending-up. He is doing something secular with our icons; he's not treating them as if they are holier and transcendent and above being human. He is treating them as being immensely, fully human. The Queen, for example, is someone we see in newspapers as an airbrushed kind of icon. He's not interested in that.

"He's looking at figures that are enormously important to him, and re-filtering them through a contemporary sensibility," he says.

The unsettling effect, and the effort to capture the strange space between comedy and horror, is a deliberate ploy in his work. It is designed to self-consciously disarm the viewer's expectations. As Condo says, "I like people to walk into one of my exhibitions and say, 'What happened?'"

George Condo: Mental States, Hayward Gallery, London SE1 (020 7960 4200) 18 October to 8 January 2012. Drawings by George Condo, Sprueth Magers, London W1 (020 7408 1613) 11 Octoberto 12 November 2011 www.spruethmagers.com