This chapter examines cultural discourses about the visual arts in the ancient world, and the ways in which those discourses intersected with other areas of Greek and Roman critical thinking. After surveying debates about the very delineation of ancient materials as “art,” and the importance of those debates within the modern disciplinary frames of “Classics,” “Classical archaeology,” and “art history,” the chapter examines the rise of different cultural discourses for theorizing the manufacture of images in Classical antiquity, above all in the Hellenistic and Roman worlds. From this perspective, the second part of the chapter then turns to examine different attempts to write “histories” of painting and sculpture in Greece and Rome, focusing on Pliny the Elder's Natural History. Third and finally, we consider Hellenistic and Roman rhetorical traditions of comparing personal “styles” in painting and sculpture to individual modes of verbal expression, with special reference to Quintilian's Institutes of Oratory. Throughout, the aim of the chapter is twofold: first, to demonstrate how Greek and Roman ideas about images resonated against other areas of “aesthetic” thinking; and second, to explore both the similarities and differences between “ancient” and “modern” notions of what art is – or might be.