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Marxist cultural theorist Walter Benjamin devised his conception of the dialectical image as a prompt to understanding and action at a time in which it was possible to believe that shock had a self-evident revelatory power. With the advent of late capitalism, this epistemological presumption is difficult to maintain. How, then, might Benjamin's conception be refurbished for an era in which shock is no longer shocking? In this paper, I revisit the output of Mark Lombardi and Cindy Sherman, two canonical postmodern artists whose work corresponds in some ways to Benjamin's project while at the same time introducing modes of visual seduction that might draw the viewer back to the experience of shock—not as an aesthetic conceit, but rather as a mode of analytic reckoning.