Unseen Basquiat, Riffing on Leonardo, Leads Christie's Sale at $30M

Christie's will offer a long-unseen Jean-Michel Basquiat canvas, Untitled (Leonardo and His Five Grotesque Heads), with an estimate "in the region of" $30 million as the lead lot of its 21st Century Evening Sale in New York on November 19.

The auction house announced the sale on Tuesday. The painting has not been shown publicly in more than two decades and emerges from what Christie's described as a "distinguished" private European collection.

The work measures 84 by 84 inches and responds directly to Leonardo da Vinci's grotesque heads, a series of ink sketches made between the late 15th and early 16th centuries. Those caricatures functioned as commentary on current events as much as anatomical studies, and they stand in jarring contrast to Leonardo's customary grace.

Which Leonardo drawing did Basquiat choose?

Basquiat drew on A Man Tricked by Gypsies (formerly titled Five Grotesque Heads), circa 1493. Leonardo's drawing satirized the social unrest caused by the arrival of the Romani in Western Europe around 1420.

Basquiat carries over all five of Leonardo's heads, along with the drawing's irreverent edge. Where Leonardo exaggerated his subjects' expressions with a light hand and still gave them bodies, Basquiat strips them down: a slimy grin, a simian grimace, and a howling mouth. Above the heads reads "Muy Fao," a phonetic misspelling of the Spanish muy feo — "very ugly." A pink patch in the bottom-right corner contains the words "ALTER EGO," which Christie's said refers to the artist himself.

"Few paintings show Basquiat so directly wrestling with the weight of art history," Ana Maria Celis, Christie's head of post-war and contemporary art, said in a statement. "We know Basquiat was enthralled with Leonardo's sketches from a young age, and in Untitled (Leonardo and His Five Grotesque Heads) we see him improvising off the great Master while tackling one of the canon's most affecting themes, The Grotesque. Characteristically, Basquiat is able to completely reinvigorate the theme, recontextualizing it among the duplicities and the excesses of 1980s New York."

What does this change for the market?

The sale revives the question of where Basquiat's market ceiling now sits. The artist held the record for the most expensive work by an American artist ever sold at auction after Untitled, a 1982 skull painting, fetched $110.5 million at Sotheby's in 2017, bought by the Japanese billionaire Yusaku Maezawa. That 1982 canvas carried a pre-sale estimate in excess of $60 million and sold for nearly double.

Andy Warhol reclaimed the American record in 2022, when his 1964 Shot Sage Blue Marilyn sold at Christie's in New York for $195 million, including the buyer's premium.

The Leonardo-inspired painting comes to market at roughly half the estimate of the 2017 record-setter. Whether demand on November 19 can push its price toward Basquiat's auction high will be the test for a market that, as Christie's own framing suggests, still treats the re-emergence of a major unseen canvas as something close to a miracle.