With the expression “apophatic aesthetics,” Amador Vega names different cases of twentieth-century hermeneutics of negativity that show a spiritual debt to negative theology and in particular to the major mystical trends of Medieval Europe. Our aim here is to explore how this category applies to the artistic work created by the contemporary artists Arakawa and Gins. However, our focus is not on the debt of these artists to apophatism in the Christian tradition but in Buddhism, especially in Zen. Through an analysis of various artworks, the article intends to determine the reminiscences of the evocation of emptiness in Zen-related arts. By so doing, despite the lack of continuity with tradition, it seems possible to uncover certain links with Japanese classic aesthetics. At the same time, since emptiness is a notion revisited in modern Japanese thought, the paper raises the question of its role as an ascetic way of thought, capable of avoiding conceptual limitations and thus opening new paths to philosophy. In this sense, insofar as thinkers well known as critics of modernity, such as Lyotard, Danto, or Taylor, have dialogued with Arakawa and Gins’s artistic proposal, a connection between certain aspects of Japanese philosophy and so-called postmodern thought is suggested.