The idea that a rich aesthetic appreciation of works of art involves some acute sense of incomprehension or bewilderment can, on the one hand, seem a commonplace, a datum that any theory of aesthetic appreciation must accommodate. Thus, Siri Hustvedt writes in her essay “The Pleasures of Bewilderment” that Giorgione’s “The Tempest” “will always resist my understanding and that is why I keep going back to it,” and Clement Greenberg affirms that “this bewilderment is salutary. It does us good not to be able to explain, either to ourselves or to others, what we enjoy or love; it expands our capacity for experience.” Yet on the other hand, intuitive as this may seem, one might still wonder why we would find such experiences of bewilderment and incomprehension satisfying and salutary. Isn't it always better to understand better, and comprehend more? In this paper, I develop these questions and propose an answer. Bernard Williams once wrote that “what we value is, unsurprisingly, connected with what we believe about human beings” and so “we can try to look ‘behind’ our values for the images of humanity that support or encourage them.” This suggests that if we are to make sense of the pleasures of bewilderment, we should ask what "image of humanity" could support such pleasures and how.

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