This chapter examines Leo Tolstoy’s views on the visual arts and aesthetic debates of his time as expressed in his seminal publication What Is Art? (1897). It contextualizes the writer’s ideas about painting and representation within the principal controversies and prevalent issues of the Russian art world of 1870–90, and especially in relation to the theories and praxis of the Wanderers or Peredvizhniki. More specifically, it focuses on Tolstoy’s intellectual exchanges with and support for several of the most prominent and important artists of the day, such as Ivan Kramskoi, Ilya Repin, and Nikolai Ge, highlighting the discursive intersections between his writing and their paintings, and the broader politics of intermediality in nineteenth-century Russian realism.