During the 1960s, Andy Warhol's use of photo booth machines marked a significant advancement in his artistic methodology. Not only did he utilize these devices extensively in various portraiture projects, beginning with his commissioned portrait of the collector Ethel Scull—famously capturing her within an automated photo booth on 42nd Street—but their sequential format also informed his compositional approach to other works. An exemplar of this influence can be seen in his 1964 portraits of Jacqueline Kennedy, which were derived from images disseminated through news media.

The idea of this photograph came to William John Kennedy's as he approached the entrance of Warhol’s studio on East 47th Street and observed a man donned in an advertising sandwich board. Kennedy, perceiving Warhol as 'the ultimate self-promoter,' undertook the task of constructing a sandwich board bearing the artist’s iconic self-portraits, likely completed only weeks prior. Numerous photographs were taken of Warhol donning this curious accessory, as if he were engaging in an exaggerated act of street-level self-promotion—an act that was strangely prophetic of the artist’s later appearances on New York’s sidewalks, where he distributed copies of Interview magazine.

With Kennedy positioned above the artist on the stairs of the firescape, Warhol arranged the canvas so that it tilted nearly perpendicular to his face, as though employing it as a mirror to cast his reflection upward towards the camera. The photograph, captured in sharp focus and illuminated by natural light, presents the artist in stark contrast to the idealised self-portrait—implying a perceived dissemblance between Warhol and the self-image he sought to project publicly.

Here, Warhol is presented as if clad in a manner akin to a street hawker’s sandwich board, a traditional guise associated with itinerant vendors. The urban textures of The Factory’s iron fire escape and the flattened printed board serve as a compelling study in contrasting tactile surfaces. Kennedy's perceptive insight was to expose Andy Warhol as both a private individual and an extraordinarily public artist by integrating him into his own artworks—an approach that this image exemplifies with particular wit, predating Warhol’s explicit articulation of his ‘Business Art’ philosophy.

The particular photograph is unique in so far as it is the only photographic print that was ever pulled from an intended edition of five, made in 2005 from the 1964 negative.