The Defense of Holy Images by John of Damascus stands as the archetypal exposition of the Christian theology of images. Written at the outbreak of the Iconoclastic Controversy, it has been mostly valued for its theological content and given scholarly short shrift as a narrowly focused polemic. The work is more than that. It presents a complex and profound explication of the nature of images and the phenomenon of representation, and is an important part of the “history of looking”in western culture. A long chain of visual conceptions connects classical Greek and Roman writers, such as Homer and Quintilian, to John: the living image, the interrelation of word and image, and image and memory, themes elaborated particularly in the Second Sophistic period of the early Common Era. For John to deploy this heritage so skillfully to the thorny problem of the place of images in Christianity, at the outbreak of a violent conflict that lasted a further 100 years after his writing, manifests an intellect and creativity that has not been sufficiently appreciated. The Defense of Holy Images, understood in this context, is another innovative synthesis of Christianity and classical culture produced by late antique Christian writers.