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In this paper, I compare aspects of Heidegger’s and Dewey’s thinking and argue that such a comparison is educationally promising. I develop this argument primarily by examining each author’s understanding of art, which shows striking similarities. Both Dewey and Heidegger iframed art and aesthetics as favorite noetic experiences, conceiving of them as something that not only completed thinking but that were necessary for thinking to happen. I also argue, however, that, through the lens of art, we can reframe and better understand some aspects of their thinking, namely, Dasein’s projecting in Heidegger and the gap between experience and thinking in Dewey. These correspondences, in turn, allow us to conceive of education as “leap” and “transcendence,” an understanding that is related to the human duty of bearing and preserving our groundless condition.