This essay explores the parallel rising of computer vision technology and digital art history, examining some of the current possibilities and limits of computational techniques applied to the cultural and historical studies of images. A fracture emerges: computer scientists seems to lack in the critical approach typical of the humanities, a shortfall which sometimes condemns their attempts to remain technological curiosities. For their part, humanists lack in technical knowledge that is needed to directly investigate big archives of images, with the result that art historians often must limit their attempts in the computer-aided inquires on texts or metadata databases, a task that does not imply the study of the images themselves. A future dialogue between the two areas is claimed as a necessity in order to foster this new branch of knowledge.