NEW YORK, NY.- Christie's announced a masterpiece by Jean-Michel Basquiat, Untitled (Leonardo and His Five Grotesque Heads), which will be offered in the 21st Century Evening Sale on November 19 during 20/21 Fall Marquee Week. The monumental 84 x 84-inch painting is Basquiat's interpretation of Leonardo DaVinci's celebrated Grotesque sketch from circa 1493, A man tricked by Gypsies (Formerly Five Grotesque Heads). It has been in the same private collection for over two decades, unseen by the public. Estimated in the region of $30 million, Untitled (Leonardo and His Five Grotesque Heads) will be the top lot of the sale.

Ana Maria Celis, Head of Post-War and Contemporary Art, remarks: “We are delighted to present Untitled (Leonardo and His Five Grotesque Heads), a powerful masterwork by Jean Michel-Basquiat, as the leading highlight of November's 21st Century Evening Sale. Few paintings show Basquiat so directly wrestling with the weight of art history. 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. A jewel within Basquiat's oeuvre hidden for the last twenty years, this canvas represents the artist at his very best, and it is an absolute pleasure to present to the market this fall.”

Thematically, the painting centers on a dialogue between two canonical giants spanning continents and centuries, placing two artistic geniuses at odds—Basquiat and Leonardo Da Vinci. The work's source is a Da Vinci sketch in the United Kingdom's Royal Collection, which depicts five male heads with grotesque expressions and exaggerated facial features. The drawing is the most elaborate of the Renaissance master's series exploring the notion of The Grotesque—a formal proposition of the intentionally distorted, misshapen and fantastical as a counter to classic ideals of beauty—provoking both discomfort and fascination.

In monumental scale, Basquiat revives Da Vinci's five subjects now 500 years later, reinterpreting the concept of grotesque from his own contemporary vantage point. A young Black artist working in the disproportionately white art scene in the 1980s, Basquiat felt the investigation of history to be crucial in understanding the shape of his own cultural experience. In a society rife with unrelenting violence and racial injustices, Basquiat used art making to interrogate systems of oppression and contextualize his own existence within them. In a grid-like framework across a blazing orange canvas with passages of turquoise and royal blue, he calls into questions the construct of faces deemed universally unseemly, juxtaposes anatomical images with descriptive words and phrases including: “TEETH.” “MOSTLY NOSTRILS.” and “A. GROUP OF ELDERS.” At the bottom right corner, contained within a patch of pale pink, are the words “ALTER EGO,” referring back to himself. With this text, he subverts the traditional narrative, questioning that which has been accepted, asking instead, what is it that truly defines grotesque—and who has the power to decide.