This article investigates the ideological implications of Pope Gregory the Great’s beard for Catholic reformers of the sixteenth century. It argues that the portrayal of Gregory as clean-shaven, with a “moderate” beard, or with a long bushy beard (all representations that are to be found in sixteenth- and seventeenth-century Roman art and scholarship) take us to the heart of inter- locking Catholic Reform debates on the “Romanness” of the Roman church and the vexed question of how to evaluate late antique and medieval Christian tradition for the Christian present.