Art history may take itself seriously, but art historians and their practices have often been made the butt of jokes and taken as easy targets for ridicule and satire. Though the pedant is a stock comic figure, the premise here is that art history has a special, structural, vulnerability that derives from the objects of its inquiry. This essay argues that art has the potential to subvert history by calling paradox and ambiguity into play. Accepting Jeremy Tanner’s argument that Western art history was invented in ancient Greece and that art became a topic for history when it constituted an ‘autonomous province of meaning’, works by Titian, Rembrandt, and Hans Baldung Grien provide examples of the fluid boundaries of that province. In each case artists bound their identities to works that elude interpretation and forestall high-minded historical closure