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 interlocking 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.