Encounter with Japanese aesthetics from a Western philosophical standpoint holds great potential for expanding definitions of art, beauty, perception, and expression, etc. It also affords valuable opportunities for expanding our definition of philosophy itself. If we are to treat the peculiarities we discover as more than mere cultural curiosities, I argue that implicit to intercultural encounter with Japanese aesthetics is a methodological challenge arising by virtue of the status of the artist in that tradition. While artistic practices are subject of philosophic speculation in the West, they are rarely considered to be philosophic practices, whereas in the Japanese tradition, being an artist is one way of being a Buddhist practitioner. The issue I consider is whether encounter can be truly “intercultural” if we remain reluctant to bracket our definitions of philosophy and our methodological norms, which dictate that artistic practices be considered other than or less than philosophic practices. By way of the landscape painting of Sesshū Tōyō as interpreted by the philosophy of Nishida Kitarō, I propose a new way of seeing the art of Japan, which enables a stance that expands our definition of philosophy and renders productive a double bind of intercultural encounter.