A sophisticated charcoal portrait by iconic and beloved American artist and illustrator James Montgomery Flagg, dated 1936. This severe yet fetching caricature-styled portrait of Hollywood film legend Gloria Swanson dates to her self-imposed seven year hiatus from Hollywood and was later featured prominently in the film Sunset Boulevard.  We have included a screen shot from the film which prominently shows the drawing above the mantel in the living room of Norma Desmond, one of the many real-life images of Swanson to pepper the film. Flagg created a series of similar portraits for the cover of Photoplay magazine during the years 1936 – 1938. This was likely commissioned by Photoplay for the series, but scrapped when a rumored return to film by Swanson failed to materialize. It is quite possible that Flagg found another outlet for publication, but we have yet to see this in print form. Portrait is handsomely matted and framed behind glass and in a fine state of conservation.