re: #184 sagehen
Probably the most famous American political painting:
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Norman Rockwell’s “The Problem We All Live With”, 1964
Rockwell is actually considered more of an illustrator and called many of his own works “pictures” instead of paintings. I’m not sure, but I am guessing many of his works were not even on stretched canvas but on illustration board.
That is not to take anything away from his works much of them done for books and magazines under contract with the publications.
Due to the nature of his work, much of his stuff could be considered political as well as story telling about America.