The Joe in question is my father, Joe Deneroff, and the drawing by cartoonist and illustrator Gilbert Bundy was apparently done in 1943 when both were working in the US Army Air Force’s fabled First Motion Picture Unit FMPU), based at Fort Roach (i.e., the Hal Roach Studio, Culver City, California). My mother said my father was hired by the Unit to work at their New York City facility in 1942; in 1943, both units were consolidated in Culver City and my father moved out there, leaving his family behind. He only stayed for six months for reasons which are not entirely clear; a letter written during the time he was there indicated he was somewhat homesick for New York, but I suspect his health problems (which eventually led to his death in 1946) were a major factor in his return.
When he returned to New York, he became an animator with Famous Studios (he had previously worked for Fleischer from 1932-40), where he worked alongside his friend Jack Ozark. When he died, Jack kept the drawing, which my father kept in his desk, and gave it to me when I got to know him in the 1980s. Jack said that my father and Bundy worked together at the FMPU and that the drawing perfectly captured the way my father acted and dressed.
In doing some admittedly cursory research. I could not find anything on Bundy and the FMPU; for instance, David Apatoff’s Illustration Art blog does note that:
… when World War II came along, Bundy decided for some reason to leave it all behind and volunteer to work as an artist in the South Pacific for Hearst newspapers.
In 1944, Bundy was accompanying the Marine invasion of Tarawa when a Japanese shell exploded in his small landing craft. …
Bundy returned to the U.S. but never recaptured the joy in his pre-war art. On the anniversary of his ordeal Bundy committed suicide, thereby rejoining his fallen comrades.
I would, of course, be delighted to hear from anyone who has any additional information on the matter.