Basquiat’s Long-Unseen Riff on Leonardo da Vinci To Lead Christie’s 21st Century Evening Sale With $30 M. Estimate

The re-emergence of a long-unseen Jean-Michel Basquiat masterpiece is a miracle the art market occasionally performs. Christie’s announced Tuesday that one will appear at its 21st Century Evening Sale this fall.

Untitled (Leonardo and His Five Grotesque Heads) will make its first public appearance in more than two decades when it leads Christie’s 21st Century Evening Sale in New York on November 19, having surfaced from a “distinguished” private European collection. The estimate is “in the region of” $30 million, according to the announcement.

Measuring 84 inches by 84 inches, the bright orange canvas responds to Leonardo da Vinci’s grotesque heads, a series of ink sketches made between the late 15th and early 16th centuries. These ghoulish caricatures were as much commentary on current events as anatomical studies, and they form a repellent contrast to the artist’s customary grace. Basquiat was drawn to A Man Tricked by Gypsies (formerly Five Grotesque Heads), c. 1493, a satirical depiction of 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 but still gave them bodies, Basquiat strips them down to their foul essence: a slimy grin, a simian grimace, and a howling mouth. Above them reads “Muy Fao,” a phonetic misspelling of the Spanish muy feo, or “very ugly.” A pink patch in the bottom-right corner contains the words “ALTER EGO,” referring to himself, Christie’s said.

“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.”

Jean-Michel Basquiat held the record for the most expensive work by an American artist ever sold at auction after Untitled, a furious 1982 skull painting, sold at Sotheby’s in 2017 to the Japanese billionaire Yusaku Maezawa for $110.5 million. (Andy Warhol reclaimed the title 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 1982 Untitled carried a pre-sale estimate in excess of $60 million and sold for nearly double that. Untitled (Leonardo and His Five Grotesque Heads) comes up for sale at half that estimate; stay tuned to see whether demand can push its price to or beyond the artist’s record.