This article argues that painting and its theory founds and subtends the discipline and practices of the history of art. It proposes this epistemological situation as a problem for visual culture. The article begins by locating the centrality of painting as intellection in the person and work of Leonardo da Vinci and in the writing on him by Paul Valéry and Walter Benjamin. An investigation of the inheritance of Leonardo da Vinci in the 17th century follows, in order to historicize his exemplarity both in early 20th-century art theory and in the dissipating aura associated with painting. The emergence of the ‘art book’ in the 17th century in Italy and France, particularly the first edition of Leonardo’s Treatise on Painting, is seen as significant in the transformation of the image and its power to represent through the materiality and characteristics of the book. This transformation, the basis of ‘the trouble with painting’, occurred amongst an elite group of connoisseurs, prelates, and aristocrats. Using images and subject matter drawn from early ‘art books’, the article revises the theories of representation in painting found in Michel Foucault and Louis Marin, among others, in order to understand more clearly what has been at stake in the espousal of the visual and the verbal in the genealogy of the literature on art.