This May, Sotheby’s will unveil a trove of rare works by Keith Haring, on offer from the collection of his lifelong best friend, Kermit Oswald. With many works unseen for decades - including one of just six known self-portraits on canvas that the artist ever made - the collection offers a new lens through which to explore Haring’s practice and legacy, and the generosity and friendships that defined it.

Executed from 1977-1989, the collection spans a large breadth of Haring’s practice and a range of media. Many of the works were given to Kermit by Keith and have remained in his private collection for nearly four decades. Led by an exceedingly rare self-portrait of the artist, exceptional carved wood sculptures, a crib and dresser painted as a gift to Kermit for his first child, the complete set of 17 screenprints, The Blueprint Drawings; as well as a range of sharply rendered works on paper showcase Haring’s earliest experimentations with imagery and the news media, among other wonderful works on found material. In Kermit’s own words, “each of Haring’s works meant something” - and it was through his art that he unveiled his iconic visual vernacular across a range of media, which have been cherished by Kermit since their creation.

The collection is illuminated by newly unveiled images of Keith Haring and personal letters written to Kermit, revealing an intimate personal portrait of the artist. In the photos, Keith can be seen smiling at Oswald’s son’s baptism, hanging out with Oswald at home, and working on wood carvings in his studio. His letters to Kermit range from his musings on various topics from the art world to technology; newspaper clips and reviews, invitations to his exhibitions; and his experimentations with images and the news media, splicing up words and re-arranging them on the page. In a letter dated to April 1981, Haring writes to say that he had been thinking about the conversations they had at the MoMA sculpture garden about computers and evolution. He also references 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 The Crystal Bridges Museum of American Art, Bentonville, Arkansas.

Works will be on public exhibition at the Breuer beginning 2 May.

Keith Haring and Kermit Oswald first met in Sunday school in their Pennsylvania hometown, though Oswald’s most vivid early memory of Haring is watching him come through the doors of their kindergarten class. Immediately bonded by their shared love of art from a young age, they began drawing together from around six or seven years old. “Our heads were connected from the time we were kids”, said Oswald. The pair might have been better described as family than just friends - in Oswald’s words: “If I wasn’t having dinner at Keith’s house, he was having dinner at mine.” They would deliver their paper routes together, challenging each other to races to see who could deliver their route the fastest, with the loser buying ice cream sundaes. As teenagers, they’d catch a $10 bus to Manhattan and spend the entire day visiting museums and galleries and then would come home and paint late into the night inspired by all that they saw. On occasion, other nights were spent graffitiing overpasses, or once even painting their high school’s white vans under cloak of darkness. Though Haring moved to New York City in 1978 to begin studying at the School of Visual Arts, they continued sending letters back and forth, sharing ideas and continuing to work together throughout the years, taking jobs together painting artist’s studios in New York City. Kermit was entrusted with building the workshop in Keith’s studio, building each frame used and installing every exhibition. Keith would often visit the Oswald family, and was Kermit’s son's godfather. As described by Kermit - their friendship was pretty close to perfect.

Executed in 1985, Keith Haring’s Self-Portrait (est. $3-5 million) is one of just six known self-portrait paintings on canvas ever created by the artist. One afternoon, Keith called Kermit to invite him to his studio, and asked him to select a work of his choice. Oswald recalled being immediately drawn to this work because of Keith’s daring self-immortalization as part sphinx. To create the portrait, Keith asked someone to take a polaroid of his face, which he used as reference to paint himself. Oswald held the work in his collection for more than 40 years, remarking that not a day went by where he didn’t think that it was one of the most beautiful paintings Haring ever made.

Keith Haring would frequently visit the Oswald family and was the godfather of Kermit’s son. Testament to his generosity and friendship, Haring offered to paint a crib and dresser (each estimated $250,000-350,000) as a gift to Oswald ahead of the birth of his first child. Originally Oswalds from his childhood, Haring painted them in a new vibrant yellow, and added his signature iconography including images of dachshunds to depict the Oswald family dog, and two playful figures on the opposite which are meant to represent Kermit and his wife, Lisa. All four of Kermit and Lisa’s children used the crib and dresser.

Untitled, a carved wood sculpture from 1983 represents the spirit of urban art with the elegance of fine art for which the artist is best known (estimate $600,000-800,000). Keith Haring was among the first group of artists to successfully transition from the street to the studio, shaking up the 1980s art scene with his instantly recognizable visual language. Towards the end of 1983, Haring began experimenting with carved wood sculptures, discovering a method to carve his trademark lines into the surface of the material to create a three-dimensional effect. He learned about the wood-working process from Kermit Oswald, whose father was a carpenter. Using a wood router, Haring was able to quickly carve intricate patterns into wood reliefs. Untitled was part of the sensational new body of work created for the now legendary exhibition at Tony Shafrazi Gallery which took place at the end of 1983 and into 1984. Haring unveiled a series of extraordinary enamel on wood paintings and sculptures, which have since been regarded among his most influential.

The complete set of 17 screenprints, The Blueprint Drawings, rarely appear on the secondary market, and were created in the final months of Haring’s life in 1990 (estimate $300,000 - 500,000). This set of screeprints was personally dedicated by Haring to Kermit and his wife Lisa, underscoring the incredibly personal tenor of the collection. The Blueprint Drawings is a masterclass in Haring’s iconic visual vernacular, demonstrating a complex narrative tableaux, created at the apex of Haring’s artistic development.

In the 1980s, Keith visited Oswald’s wood working studio, where Oswald had created a wood piece – Haring’s first encounter with the ‘stair’ form. Depicting his iconic figure falling down a flight of steps, Untitled (estimate $150,000 – 200,000) serves as Haring’s response to the minimalism movement at the time, and a reflection of his desire to share his ideas with the world through his art.

This October, a selection of 41 works will be offered in a dedicated online auction. Featuring works on paper, collages, sculpture and ephemera, the auction presents a survey of early to mature examples of works that embody the diversity of materiality in Keith’s practice. The auction is led by a vibrant late painting, carved wood sculptures and rare early collage works on paper.