A singular, tri-color self-portrait; a bright-yellow baby’s crib adorned with whimsical caricatures; a painting of a figure falling down a blue flight of stairs. Keith Haring gifted these intimate works and many others to his childhood best friend and fellow artist, Kermit Oswald, over the course of his lifetime.
For four decades, Oswald has held a trove of rarely seen works by his dear friend, created between 1977 and 1989, including one of only six self-portraits known to exist of the artist. This month, the works are going under the hammer at Sotheby’s, providing the public with a glimpse into one of Haring’s most intimate relationships.
On May 2, the auction house unveiled 41 of Oswald’s closely held works by Haring, spanning his paintings, sculptures, and letters, as part of an exhibition at Manhattan’s Breuer building. Sotheby’s will also offer photographs that Oswald took of Haring, including a snapshot of the artist holding his son.
The free public viewing precedes a series of three auctions of Oswald’s Haring collection — commencing on May 14 and running through October — expected to fetch millions of dollars.
Over the course of the men’s friendship, curator Jeffrey Deitch said in a press release, Oswald and his wife Lisa developed one of the “most significant” collections of Haring’s works.
The men forged their decades-long friendship during their boyhood Sunday School days in their shared hometown of Kutztown, Pennsylvania, quickly bonding over a love for drawing. Inseparable early on, the two would frequently eat dinner at each other’s houses as children, and take bus trips to Manhattan to view art in the city’s museums and galleries. Both friends would become artists, inspiring one another through their practices.
Though Haring moved away from Pennsylvania to attend the School of Visual Arts in New York City, he maintained a close artistic and personal correspondence with Oswald.
A crib and dresser set Haring made for Oswald’s son in 1986 (photo courtesy Sotheby’s)
After Oswald asked Haring to be his son’s godfather, Haring painted a crib yellow and covered it with sketches of wagging dachshunds and playful characters rendered in his signature style. He also painted a corresponding yellow dresser with anthropomorphic features, inscribed “For Lily, Love Keith.” Both of these gifts, ultimately used by all four of Oswald’s children, are expected to sell for $250,000 to $350,000.
Sotheby’s is also offering one of the only known self-portraits of Haring, painted in 1985. The red, white, and black rendering portrays the artist as part sphinx, a detail that drew Oswald toward the painting when Haring let him take home a work of his choosing. According to Sotheby’s, Oswald believed the self-portrait — now anticipated to be worth between $3 million and $5 million — was one of the most beautiful works Haring ever created.
Another work featured in the show is an untitled wood-on-enamel sculpture Haring created for his 1983 exhibition at Tony Shafrazi Gallery. Over the course of their friendship, according to Sotheby’s, Haring visited Oswald’s woodworking studio, where he was inspired to work with the medium.
In addition to the artworks Haring gifted to Oswald, the upcoming auction features letters between the two artists and friends, including musings on the relationship between art and technology at the time. Together, the works make up a “survey of Haring’s early illustration,” said Sotheby’s Vice President of Contemporary Art Kathleen Hart, that “together trace the evolution of his iconic visual vocabulary.”
