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Fine Art
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Rare Trove of Keith Haring Works Make Auction Debut at Sotheby's

Published on
April 23, 2026
Rare Trove of Keith Haring Works Make Auction Debut at Sotheby's
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This May, Sotheby’s will offer a group of rare works by Keith Haring from the collection of his lifelong best friend, the artist Kermit Oswald. Executed from 1977 to 1989 and spanning a range of media, many of the works were gifts from Haring to Oswald and have remained in private hands for nearly four decades. All will make their auction debut.

The offering is led by an exceedingly rare 1985 Self-Portrait (est. $3 million to $5 million), one of just six known self-portrait paintings on canvas the artist ever created. Haring invited Oswald to his studio to choose a work, and Oswald was drawn to this piece, in which the artist depicted himself as part sphinx, working from a polaroid of his face. He held it in his collection for more than forty years.

Keith Haring, Self-Portrait, 1985 (est. $3 million to $5 million)
Keith Haring, Self-Portrait, 1985 (est. $3 million to $5 million)
A crib painted by Keith Haring as a gift for Kermit Oswald’s first child (est. $250,000 to $350,000)
A crib painted by Keith Haring as a gift for Kermit Oswald’s first child (est. $250,000 to $350,000)

Further highlights include a crib and dresser (each est. $250,000 to $350,000) that Haring painted as a gift ahead of the birth of Oswald’s first child, adding his signature iconography in vibrant yellow, including dachshunds representing the family dog and two figures representing Kermit and his wife, Lisa. A carved wood sculpture, Untitled (1983, est. $600,000 to $800,000), belongs to the body of enamel-on-wood work Haring created for his 1983 to 1984 exhibition at Tony Shafrazi Gallery; he learned the wood-working process from Oswald, whose father was a carpenter. A second Untitled (est. $150,000 to $200,000) depicts Haring’s iconic figure falling down a flight of steps, his first encounter with the ‘stair’ form, seen at Oswald’s wood-working studio.

Haring and Oswald first met in Sunday school in their Pennsylvania hometown of Kutztown and began drawing together around the ages of six or seven. As teenagers they took a $10 bus to Manhattan to spend the day visiting museums and galleries, then painted late into the night. Haring moved to New York City in 1978 to study at the School of Visual Arts, and the two continued to exchange letters and work together, with Oswald building the workshop in Haring’s studio and installing his exhibitions. Haring was godfather to Oswald’s son. The collection is illuminated by photographs and personal letters, including one dated April 1981 in which Haring reflects on conversations about computers and evolution and mentions receiving his third court summons for his subway drawings.

The auction coincides with major surveys of Haring’s work, including Keith Haring at The Brant Foundation, New York; Keith Haring: In The Street at Free Parking, New York; and the upcoming Keith Haring in 3D at Crystal Bridges Museum of American Art, Bentonville, Arkansas. The works will be on public exhibition at The Breuer beginning 2 May. This October, a further selection of 41 works, including works on paper, collages, sculpture, and ephemera, will be offered in a dedicated online auction.

(Press Release)