Monumental Basquiat Self-Portrait Unseen Since 1999 to Appear at Sotheby’s

A self-portrait by Jean-Michel Basquiat hidden from public view for nearly a quarter-century is set to be a marquee lot of New York’s fall auction season.

The eight-foot-tall Self Portrait as a Heel (Part Two), from 1982, will be offered during Sotheby’s evening auction of contemporary art on November 15, where it’s estimated to fetch between $40 million and $60 million. A high-quality Basquiat of such size is a rarity at auction; the last comparable offering was an untitled skull painting from the same year that sold for a record-setting $110 million at Sotheby’s in 2017.

Though Self-Portrait is not expected to edge or surpass that number, selling within its estimate would make it one of the the most highly valued works by Basquiat ever brought to a public auction.  

Per Sotheby’s, Basquiat made the self-portrait while living in the Venice home of dealer Larry Gagosian, who later organized the artist’s first show on the West Coast. Sotheby’s specialists believe it reflects Basquiat’s experience in Los Angeles as a rising art star with relative anonymity in Los Angeles. He created three works during this highly prolific period incorporating the word “heel,” a slang term for punk or delinquent. Additionally, in professional wrestling, the “heel” is the villain or foil to the match’s hero. 

David Galperin, head of contemporary art for Sotheby’s America, said in a statement, “Unlike other paintings by Basquiat that have sly references to himself, this painting self-consciously renders an image not only of who he understands himself to be but also of the way he felt others would inevitably perceive him—a testament to his own searching for himself and his vision for the lasting legacy of his artwork.”

Self-Portrait as a Heel, the Sotheby’s painting’s 1982 counterpart, sold for $5.9 million (with fees) at Christie’s in New York in 2010; the final work in the series, Hollywood Africans (1983), is in the permanent collection of the Whitney Museum of American Art.

Self-Portrait as a Heel (Part Two) last appeared publicly in 1999, when it sold at Christie’s for $772,000. It was previously owned by Belgian collector Stéphane Janssen, who was an early patron of Basquiat, purchasing the painting from Gagosian shortly after its creation. According to the Art Newspaper, the consignor acquired the self-portrait from the London gallery Blain Southern prior to its shuttering in 2020. Self Portrait as a Heel (Part Two) will be exhibited at Sotheby’s New York galleries starting November 1.