Portrait of Vollard II is an aquatint executed by Pablo Picasso in 1937, signed in red pencil in the lower right margin — the red signature itself an unusual and deliberate touch that sets the work apart from the standard black or graphite signing of most Picasso prints. The subject is Ambroise Vollard, the legendary Parisian dealer and publisher who had been one of the most important figures in Picasso's career since their first association in the early 1900s, when Vollard purchased a large body of work from the young Spanish artist and effectively launched his commercial reputation in France. By 1937 their relationship spanned nearly four decades, and the portrait carries the weight of that history.

Vollard was one of the great subjects of early twentieth-century portraiture — Cézanne, Renoir, Bonnard and Denis all painted him, and Picasso himself produced multiple images of the dealer across different media and different decades. Portrait of Vollard II belongs to a sequence of aquatint portraits produced in connection with the Vollard Suite, the monumental series of 100 prints that Vollard had commissioned from Picasso in 1930 and which was completed by 1937, the year of this work. The aquatint technique — in which tonal areas are built up through acid biting of a resin-coated plate — allows a painterly range of greys quite unlike the bitten line of etching, and Picasso exploits it here to full effect, building Vollard's massive, heavy-featured face from a complex field of tonal gradations that gives the image the quality of a photograph or a mezzotint.