When Christie's concluded Sir Elton John's spectacular eight-part auction series in February 2024, bringing in $20.5 million from over 900 items, most headlines focused on the $1.9 million Banksy triptych and the $94,500 platform boots. But quietly positioned within the "Elton's Superstars" photography collection was Herman Leonard's 1948 photograph of jazz legend Dexter Gordon at the Royal Roost in New York—a gelatin silver print, printed in 1988, signed, titled, dated and numbered '6/50' in pencil.
The Photograph That Defined Cool
Herman Leonard's iconic 1948 photo became "the definition of 'cool'" and helped establish the visual vocabulary for how we imagine jazz musicians. Leonard's masterful use of dramatic lighting and atmospheric smoke didn't just document a moment—it created an archetype that has endured for over seven decades.
The journey of this particular print tells a broader story about artistic legacy and market recognition. Bearing museum labels from both the Sir Elton John Photography Collection and previous exhibitions, including its display at the High Museum of Art's "Chorus of Light: Photographs from the Sir Elton John Collection" from November 2000 to January 2001, the photograph had already achieved institutional validation before entering the auction market.
Distinguished Company in Contemporary Collections
The company Gordon kept in John's collection reveals something significant about current perceptions of cultural hierarchy. The "Elton's Superstars" section featured Edward Steichen's portrait of Gloria Swanson behind a sheer veil and Richard Avedon's head-on portraits of the Beatles. Irving Penn's series of over-life-size close-ups of Miles Davis' hands, and classic pictures of Billie Holiday, Charlie Byrd and Chet Baker shared equal billing with Gordon's image.
John's broader photography collection features works from over 140 photographers, including Robert Mapplethorpe, Cindy Sherman, Diane Arbus, Sally Mann, Zanele Muholi and Ai Weiwei, with portraits of famous performers including Marilyn Monroe and Miles Davis. That Gordon's photograph earned a place among these contemporary art world luminaries speaks to his continuing cultural currency.
The "Elton's Superstars" online sale alone made $587,916, demonstrating robust market appetite for celebrity portraiture across generations and genres.
A Market That Looks Forward
What makes this auction significant isn't just the financial figures, but what they reveal about evolving taste and value recognition. John assembled one of the world's largest private photography collections, totaling some 7,000 images, and his curatorial choices have repeatedly proven prescient as market indicators.
The fact that Herman Leonard's work—taken when he was just 25 years old in 1948—continues to command attention in elite auction houses speaks to photography's power to transcend its original context. As jazz celebrates its second century and photography approaches its third, the convergence of these art forms in contemporary collecting suggests new possibilities for how we understand and value cultural inheritance.
The Contemporary Relevance
Born in 1923, Dexter Gordon would have turned 102 this year. Thirty-five years after his passing in 1990, his image retains not just nostalgic appeal but active cultural relevance. The presence of Leonard's photograph in John's collection—alongside works that define contemporary visual culture—suggests that jazz's golden age figures are being reassessed not as historical artifacts but as continuing influences in modern artistic discourse.
As John and David Furnish's collection travels to major exhibitions, including the V&A's "Fragile Beauty" showing over 300 photographs from their collection, Gordon's image continues to find new audiences and contexts, ensuring his visual legacy remains part of the contemporary art conversation.
The preservation efforts led by The Dexter Gordon Society, established by Maxine Gordon, Gordon's widow and biographer, as a nonprofit cultural organization in 2013, have helped maintain this relevance. Through her seminal work "Sophisticated Giant: The Life and Legacy of Dexter Gordon" (University of California Press) and her ongoing archival research and historical preservation, Maxine Gordon has ensured that her husband's artistic contributions remain accessible to new generations of collectors, curators, and cultural institutions.
As art markets continue to expand their definition of valuable cultural assets, Leonard's photograph of Gordon serves as both historical document and contemporary commodity—proof that great art transcends the boundaries of time, genre, and market category.
A Constellation of Cultural Icons
The breadth of cultural figures represented in John's "Elton's Superstars" collection reveals the scope of his curatorial vision. The collection featured an extraordinary constellation of 20th-century icons spanning music, film, literature, and art. Musical legends included Ray Charles, Jim Morrison, Kurt Cobain, John Lennon and Paul McCartney, Miles Davis, Chet Baker, and Mick Jagger alongside Jerry Hall.
Hollywood's golden age was represented through portraits of Marilyn Monroe, Sophia Loren, James Dean, Joan Crawford, Ava Gardner, Marlene Dietrich, and Clark Gable. The collection also encompassed literary and artistic giants such as Andy Warhol, Francis Bacon, Salvador Dalí, Picasso, and Lucian Freud, alongside cultural figures like Muhammad Ali, Rudolf Nureyev, and Jacqueline Kennedy. This remarkable assembly demonstrated how John's collecting transcended simple celebrity fascination to create a comprehensive visual archive of cultural influence across multiple generations and artistic movements.
