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While realistic portraiture did not emerge in Muscovy until the late seventeenth century, the format had long flourished elsewhere. In the sixteenth century rulers from the Tudors to Venetian doges to Ottoman sultans commissioned portraits to display sovereignty and legitimacy; reproductions played to an eager audience who considered portraits windows into a ruler’s character. Not surprisingly, when Europeans first encountered Russia through diplomacy, they commissioned portraits of this new land’s ruler. In 1525 Paolo Giovio asked Russian diplomat Dmitrii Gerasimov to sketch Vasilii III; Sigismund von Herberstein instructed distinguished Viennese engraver Augustin Hirschvogel on a portrait of the same grand prince in 1549. Here we analyze how these two portraits combined some degree of eye-witness with the engraver’s art to portray an unfamiliar ruler to a curious European audience.