Christie's has revealed the anchor lot of its 21st Century Evening Sale in New York on 19 November: Jean-Michel Basquiat's Untitled (Leonardo and His Five Grotesque Heads), carrying an estimate in the region of $30 million. The painting has been out of public view for more than two decades and has come out of what the auction house calls a distinguished private European collection.

The canvas measures 84 inches square and is washed in vivid orange. Its subject is Leonardo da Vinci's celebrated grotesque-head sketches, the ink caricatures of craggy, contorted faces the Renaissance master drew around the turn of the 16th century. Basquiat borrows all five figures from Leonardo's A Man Tricked by Gypsies, made around 1493, and replays them as grimacing, howling mouths stripped back to raw expression.

Basquiat scrawls the phonetic Spanish phrase "MUY FAO" across the composition — a misspelling of "muy feo", meaning "very ugly" — while a pink patch in the lower right bears the words "ALTER EGO", which Christie's reads as the artist pointing at himself. The house's head of post-war and contemporary art described the work as a young painter riffing on an Old Master, bringing the grotesque into the chaos and excess of 1980s New York.

The consignment returns Basquiat to the November spotlight. His 1982 skull painting Untitled set the auction record for an American artist when it sold for $110.5 million at Sotheby's in 2017 to collector Yusaku Maezawa; Andy Warhol later took that benchmark with the $195 million sale of 1964's Shot Sage Blue Marilyn at Christie's New York in 2022.