In addition, a fine copy of the first edition of Leaves of Grass. Brooklyn: [For the author by Andrew and James Rome,] 1855 will be on offer in the June sale (estimate $150/200,000). Of the 795 copies comprising the first edition and printed on the small handpress of the Romes in Brooklyn, only 337, including the present work, were bound in the publisher’s dark green coarse-ribbed cloth, the most ornate of the original cloth bindings. Published in July 1855 and met with extreme controversy due to its vivid sexual imagery, Leaves of Grass today is regarded as one of the most important contributions to the canon of American poetry by one of the country’s greatest literary minds. Whitman notoriously reworked the compilation of poems until his death in 1892, resulting in markedly different versions. One of the most attractive, if fragile, books in American literature, Whitman’s self-published poetical manifesto was also at least partially typeset by the author. The present work is part of the first issue, before the insertion of press notices and before the deletion of much of the gilt from the covers and page edges. Underscoring the rarity of these treasured poems, the present work bears an engraved frontispiece portrait of Whitman by Samuel Hollyer, drawn after a photograph and printed on thick paper, which retains its original tissue-guard.

A diverse group of twelve works by Andy Warhol chart the development of the iconic artist’s career: from delicate 1950s drawings of male figures to his powerful and brazen nudes created in the mid to late 1970s. The group is led by two prints each depicting a Male Torso, rendered in electric hues and dating from 1976 and 1977 respectively (estimates $90/120,000 each). Notably, the acrylic silkscreen on canvas from 1976 was a gift from Warhol to Victor Hugo, partner of famed designer, Halston and frequent model for the artist’s Torso series.

Further highlights of Contemporary art include a strong selection of works by Martin Wong, David Wojnarowicz and Luis Frangella. In particular, Untitled (Steak on a Plate with Warriors) from 1987 presents a collaboration between Wojnarowicz and Frangella, offering a window into the thriving queer art scene of downtown New York in the 1980s (estimate $12/18,000). The present work on paper will make its auction debut in the June sale, having resided in the same private collection since it was acquired directly from Frangella.

The selection of photographs on offer are highlighted by Catherine Opie’s Dyke from 1993 (estimate $20/30,000). The last from an edition of only eight, the striking work from Opie’s Portraits series offers a blunt visual counterpoint to mainstream heterosexual culture. Rather than focusing on her subject’s face, in the present photograph Opie trains her camera on the back of a woman whose cropped hair and fair skin are punctuated by a tattoo of the word ‘dyke’ at the nape of her neck. By claiming a moniker that in other contexts might be a slur, the sitter proudly owns her sexuality – and by extension, her chosen community – etching it permanently on her body. The vivid blue damask used for the backdrop alludes to traditional materials and conservative values, as does the Old English font of the tattoo. Opie brilliantly juxtaposes the overall formal harmony of the picture with its subversive context to make a complex image exploring nuances of sexuality and gender.

Selected Images by PaJaMa – the photographic collaborative comprised of Paul Cadmus, and married artists Jared and Margaret French – further accentuates the June offering (estimate $15/25,000). The group of 10 photographs was gifted to Jon Anderson, who was Cadmus’ lover for the last three decades of his life. Included among the gelatin silver prints are portraits of the artists themselves, as well as Fidelma Cadmus, George Tooker, José Martinez and others, many of them titled by Paul Cadmus in pencil and four with ‘Collection of Paul Cadmus’ and ‘Collection of Jon Anderson’ stamps on the reverse. Beginning in 1937, and over the course of nearly two decades, the trio collectively staged photographs set against the backdrops of Fire Island, Provincetown, and Nantucket, among other locations. Their psychologically and sexually charged images were inspired in part by Carl Jung’s concept of the collective unconscious and often served as studies for the artists’ subsequent paintings and works on paper, four of which are also on offer in the sale. The appearance of the present photographs in the June sale marks a rare opportunity for collectors to acquire works by PaJaMa – extant photographs by the trio rarely appear at auction, as they were printed and gifted sparingly.

Further highlights from the photographs on offer include Annie Leibovitz’s portrait of Bette Midler, New York City, which depicts the icon engulfed in a bed of red roses (estimate $15/25,000). Midler became recognized as a champion of the LGBTQ community in the 1970s after frequently performing at the Continental Baths, a gay bathhouse in New York City. A variant of this image, taken after she starred in the film The Rose, was featured on the cover of Rolling Stone magazine dated December 13, 1979.