Early 20th century debates over the possibility of ‘metaphysics’ are grounded in a set of questions and answers whose central themes are already delineated in Kant’s critical philosophy. Wittgenstein and Carnap are sympathetic to Kant’s dismissal of transcendent metaphysics, but skeptical that there could be any substantive account of the fundamental conditions of our meaning-making. By contrast, Heidegger follows Fichte and the early German Romantics in seeing answers to the problems raised by metacritique not in science, but in the non-discursive forms of understanding and expression exemplified in art. This Romantic turn to art is not taken arbitrarily; it is motivated by methodological considerations that emerge within Kant’s own critical system. I take up the Kantian considerations which lead to an understanding of art as a window into the fundamental conditions of meaning-making before turning to Heidegger’s development of this line of thought. Next, I examine Carnap and Wittgenstein’s skepticism concerning the meaning of Heidegger’s philosophical terminology, focusing on what is perhaps the most problematic case: Heidegger’s talk of ‘the nothing’. I argue that this skepticism is overblown. Heidegger’s talk of the nothing is meaningful in the way that talk about figure and ground is meaningful: it serves as an ostensive indication of intersubjectively accessible structural features of our encounters with things. I conclude by drawing out the existential ramifications of the decision to speak or be silent, drawing on Audre Lorde to illustrate the place of art in making it possible for us to lead authentic lives.