Among the various iconographies of the Trinity which emerged in Christian art, the three-headed or trifrons image has a contested history. Warned about and censured by two popes, Urban VIII and Benedict XIV, this iconography, despite condemnations, was applied, however, by leading Renaissance artists and survived into the nineteenth century in folk art. This article considers its pre-Christian background, the sixteenth-century theological debates, and, finally, in a detailed engagement with a range of tricephalous images, it critically reevaluates and seeks to demonstrate the disputed orthodoxy of this iconography from a theological, artistic, and aesthetic perspective.