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The following essay tries to square the circle formed by two opposing yet inextricably entangled ways of thinking about aesthetics: as a subfield of philosophy and as the product of a uniquely dateable historical event. This invites us to interrogate the relationship between philosophy and history generally, disciplines that have eyed each other with suspicion from the moment both set about professionalizing their standards and methods in Enlightenment Europe—the very moment that witnesses the advent of aesthetics itself, most notably in David Hume and Immanuel Kant. I argue that this relationship was already fully dialectical even if that idea did not come to formal self-consciousness until Georg Wilhelm Friedrich Hegel placed it at the center of his own philosophical system. What made aesthetics loom so large in Enlightenment circles was the degree to which problems of beauty, sublimity, and taste put philosophy to the test of historical experience. But the reverse was true as well. In putting philosophy to an historical test, aesthetics opened the way for Hegel’s effort to put history to the test of philosophical reason. I hope that aesthetics will come into sharper focus when seen as both a philosophical discipline and an historical dilemma. Aesthetics’ dual status as discipline and dilemma reveals more clearly not only why it emerged when and where it did but also how the eighteenth century of Hume and Kant foreshadowed the historical, philosophical, and aesthetic program that took shape in Hegel.