A general tension in contemporary aesthetics can be described as existing between objective truth claims and historical relativity. The former is generally represented by the Enlightenment approaches and its descendants that ground aesthetic judgment in rationality. The latter characterizes the postmodern appeal to historicity and the exposure of historical prejudice. Following mostly the hermeneutical philosophy of Heidegger, Gadamer, Ricoeur, and Dupré, this paper argues how aesthetic theory, defined by either pole, inadequately accounts for historicity. In response to this critique, this paper attempts to navigate between these two poles in returning to an analysis of the nature of history and its phenomenological and ontological significance. It is in the very depth of the historical experience that aesthetics gains its greatest fecundity by means of its commitment to meaning and communication within history.