A Jean-Michel Basquiat self-portrait with an eight-figure estimate is poised to be one of the biggest lots of the New York autumn auction season, nearly a quarter century after the painting was last seen publicly.The 8ft-tall Self Portrait as a Heel (Part Two) (1982) will be the leading lot during Sotheby’s evening auction of contemporary art on 15 November in New York, where it’s expected to fetch between $40m and $60m. Provided the painting sells for within its estimate range, it would be among the most valuable of Basquiat’s works at auction—though it is unlikely to come close to his highwater mark of $110m (including fees), set by an his untitled skull painting (also from 1982) at Sotheby’s New York in 2017.Basquiat painted Self-Portrait as a Heel (Part Two) during an extended stay in Los Angeles for his first show on the West Coast, mounted by dealer Larry Gagosian, whose Venice home Basquiat stayed in before renting a nearby studio. The painting is understood to be autobiographical and about Basquiat’s experience in Los Angeles, Sotheby’s specialists say.Tamra Davis, a friend of Basquiat who directed to the 2010 documentary Jean-Michel Basquiat: The Radiant Child, says he “recreated himself” during his time in Los Angeles, saying the city “was a new town and nobody really knew him here, so he could be more free. That’s why he painted so much here”, according to a Sotheby’s release.During his time in Los Angeles, Basquiat produced three works incorporating the word “heel”. The term can describe delinquents or criminals, and the word is also used to indicate the villain or foil to the hero in professional wrestling. By calling himself the heel, Basquiat may be portraying himself as an “anti-hero” of the art world, the auction house says. A sister painting, Self-Portrait as a Heel (1982) sold for $5.9m with fees at Christie’s New York in 2010, while Hollywood Africans (1983) is part of the collection at the Whitney Museum of American Art in New YorkSelf Portrait as a Heel (Part Two) previously belonged to Belgian collector Stéphane Janssen, who was an early supporter of Basquiat’s and had acquired the painting from Gagosian by 1985. The consignor acquired the painting from London gallery Blain Southern, which shuttered in early 2020. The painting was last seen publicly in 1999, when it was sold at Christie’s New York for $772,500 with fees. Self Portrait as a Heel (Part Two) will go on public display for the first time since then at Sotheby’s New York galleries on 1 November.
