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While the communicative nature of early modern Italian portraits becomes increasingly overt, the continued prevalence of the portrait medallion might at first seem to stand against the tide of advances in creating portraits that directly engage with the viewer. Challenging this, I propose that a portrait medallion’s three-dimensionality may actually provide a stronger, albeit different, connection with the mind of a period viewer. Considering the Aristotelian belief that an image might be capable of “impressing” itself in the memory, as a seal impresses wax—a belief re-examined in the early modern period—I suggest that patrons of portrait medallions sought to make an impact on the beholder by way of the artwork’s very form. By embodying a medium and genre of representation particularly equipped to produce memories, the portrait medallion could “stamp” itself on the mind, thereby working towards the goal of early modern portraiture—perpetually commemorating period sitters.