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In the first half of the sixteenth century, the construct of the theomorphic portrait transformed Christian princes in Italy into ancient pagan deities like Neptune and Hercules. Arguably first among these was Lorenzo Leonbruno’s c. 1519 portrait of Federico II Gonzaga as Hercules on the vault of the Camera dello Zodiaco in the Castello di San Giorgio in Mantua. This paper seeks to establish the origin and development of this representational strategy by examining Federico’s commission, as well as commissions made by his father and great-grandfather, Francesco II and Ludovico Gonzaga. By considering the increasingly personalized pictorial association made between portraits of three generations of Gonzaga patrons and the figure of Hercules – the Renaissance exemplar of virtue – I root the theomorphic portrait in both the frescoed cycles of famous men (uomini famosi) that grew in popularity in the Middle Ages and in the ancient Roman imperial tradition of imitatio deorum.