This chapter evaluates the corpus of Constantinian sculpted and numismatic portraiture and analyzes the new directions in imperial representation that were introduced with the appearance of the dynasty of Constantine. The chapter draws attention to the dual character of art produced during the Constantinian era, which is evident in its highly individualized portrayals of the ruler and in its conscious duplication of images and styles adopted by previous Augusti (notably Augustus and Trajan). The chapter contextualizes the homogeneity of Constantine’s sons in imperial portraiture and evaluates the enduring contribution of Constantine and his immediate successors to late Roman art.