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This essay compares the philosophies of art of Susanne Langer and Maurice Merleau-Ponty, highlighting some differences in their approaches to the subject matter. It addresses the thinkers’ formulation of the nature of philosophy, the role of paradox, the functions of art and language, and the relationship between philosopher and artist. In the work of each thinker, I find two elements, somewhat at odds with each other. One is a general account of the cultural function of art. The other is a sort of artistic vision advanced by way of proposing a modern vocation for art. As a result, I argue that Langer develops an “outside” account of art, insofar as her work aims at explication of the creative process by way of maintaining some critical distance from it. Merleau-Ponty develops an “inside” account of art, insofar as he sees the phenomenologist as a peer to the painter, and advances an artistic vision of his own. I compare the two thinkers in order to show that they can address different audiences and pursue somewhat different goals. A charitable reading of each, keeping in mind their respective audiences and goals, could make the employment of these aesthetic theories more productive.