How can we reconfigure our way of understanding all that is, what Heidegger calls 'being' – so that we can live differently and more fittingly, together? How can we get a sense of different possibilities for being and doing, that allow for hope and change? How can things show themselves so that we heed them and feel a kind of grateful receptivity to them? To all of these questions, Heidegger's answer is 'art.' This Element aims to make sense of the incredible importance Heidegger affords art, on the one hand, and his pessimistic reflections on the possibilities for both art and life in late modernity, on the other. The author proposes that thinking of the artwork as a measure – opaque, basic, and with a regulative normative force – helps make sense of Heidegger's thinking and the promise and peril of art.