

I don’t think that there is a reference to any particular pirate painting. But the whole series seems to be inspired by the pirate pin ups of the thirties.
Advertising Fashion and Art

The original is from 1945 and probably the most iconic photo of the United States.
To me it looks like a quotation of the famous photo by Charles C. Ebbets "Lunchtime atop a Skyscraper" from 1932. Above all because I think that no photographer in the whole world can take a picture of a crossbeam with people on it without thinking of Ebbets.