First owned by Nathan Gluck, Warhol’s primary assistant from the early 1950s to the mid 1960s, Five Boys is an exceptional example of the artist’s blotted ink line drawing technique, a methodology he developed and honed as a student at Carnegie Mellon University. The rudimentary technique combines original drawing with ink transfer, a seemingly mechanical process. He would start with an initial illustration and place tracing paper over the design, then apply ink over a section of the image followed by pressing an absorbent sheet of paper over the wet ink to transfer the image. He would continue this process in small sections until the entire image was reproduced. Gluck explained Warhol’s attraction to this method: “Another reason why he liked it [the blotted line technique] so much [was that] by having your master drawing with which you made your blot, you could keep blotting it and redrawing it and blotting it each time and make duplicate images.” Through this method, we can see Warhol’s early gravitation towards repeated imagery, well before his pivot to Pop subjects.

Nathan Gluck first met Warhol because like the Pop icon, he began his career as a commercial illustrator. As an illustrator at the Rockmore Company ad agency, Gluck had frequent run-ins with Warhol, who freelanced at the agency and ran in similar circles. In 1952, the two exhibited together in a show at Loft Gallery, run by Warhol’s then-assistant Vito Giallo. The rest was history, as soon after the exhibition Giallo recruited Gluck to replace him as Warhol’s right-hand-man. Over their decade-long partnership, Gluck assisted Warhol in shaping many of his most famous illustrations, ads, and designs, as well as increasing the output of his blotted ink line drawings and developing early transitional Pop pieces before Warhol established The Factory. Cementing his legacy as a key player in the evolution of Warhol’s early oeuvre, Gluck was also tapped by the Warhol Foundation to authenticate works from this period, given his incomparable direct experience with, and knowledge of, the artist’s pre-Pop production.