by Redazione 23/10/2026
Categories: Market / Disclaimer
A monumental painting by Jean-Michel Basquiat, which has been in a private collection for over twenty years and has never been exhibited to the public, is set to go up for auction at Christie’s with an estimate of approximately $30 million. The work is inspired by a famous sketch by Leonardo da Vinci.
A meeting of two great artists, separated by five centuries but united by their ability to challenge the conventions of representation. This is the heart of *Untitled (Leonardo and His Five Grotesque Heads)*, a monumental painting by Jean-Michel Basquiat that Christie’s has announced as one of the highlight lots of its 21st-Century Evening Sale, scheduled for November 19, 2026, during the Fall 2020/21 Marquee Week. The work, measuring approximately 213 by 213 centimeters, has been estimated at around $30 million and has remained in the same private collection for over twenty years, without ever having been exhibited to the public.
The painting draws inspiration from a sketch by Leonardo da Vinci, held in the British Royal Collection and dated to around 1493, known as *A Man Deceived by Gypsies*, previously also identified by the title *Five Grotesque Heads*. The sketch depicts five male heads characterized by grotesque expressions and distorted features, in a representation that deliberately departs from the classical ideals of harmony and beauty. The drawing is considered one of the most elaborate examples of Leonardo’s explorations of the grotesque: an aesthetic category that explores the distorted, the deformed, and the fantastical, transforming them into tools capable of evoking both unease and attraction.
About five hundred years later, Basquiat revisits those figures and transfers them onto a monumental canvas, reinterpreting them through his own visual language. In his work, Basquiat arranges the figures within a grid-like structure, against a bright orange background enlivened by turquoise and royal blue accents. The faces interact with words and annotations that describe their features, including “TEETH,” “MAINLY NOSTILS,” and “A GROUP OF ELDERLY PEOPLE.” In the lower right corner, a pale pink patch encloses the inscription “ALTER EGO,” a reference that also ties the depiction to the artist’s personal life.
Textual elements that help challenge the way we observe and judge faces, questioning the criteria by which certain features are considered unpleasant or monstrous. Basquiat thus transforms the grotesque, asking who sets the boundaries of normality and who has the power to define what is beautiful or ugly. For Basquiat, engaging with art history was a fundamental tool for understanding his own cultural identity and his place in society. In a context marked by violence and racial injustice, his painting became a means of challenging systems of oppression and questioning dominant narratives.
“We are delighted to present Untitled (Leonardo and His Five Grotesque Heads), a powerful masterpiece by Jean-Michel Basquiat, as the highlight of our November 21st-Century Evening Auction. Few paintings show Basquiat grappling so directly with the weight of art history,” commented Ana Maria Celis, head of Christie’s Post-War and Contemporary Art department. “We know that Basquiat was fascinated by Leonardo’s sketches from a young age, and in Untitled (Leonardo and His Five Grotesque Heads) we see him improvising, drawing inspiration from the great Master, while simultaneously tackling one of the most poignant themes in the canon: the Grotesque. As usual, Basquiat manages to breathe new life into the theme, recontextualizing it amid the duplicity and excesses of 1980s New York. A hidden gem in Basquiat’s body of work over the past twenty years, this canvas showcases the artist at his best, and it is a true pleasure to present it to the market this fall.”
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| Christie’s to Auction a Never-Before-Exhibited Basquiat: The Monumental Painting Inspired by Leonardo Is Estimated at 30 Million |
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