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The article focuses on the analysis of four previously unpublished Neo-Latin epigrams penned by Giovan Giacomo Calandra, a leading officer and humanist serving at the court of Mantua, in celebration of Lorenzo Costa’s portrait of Isabella d’Este (1508). Art historians have long been aware that Isabella had solicited Calandra to supply her with a few elegiac couplets as a way of exalting one of the very few portraits of her which she actually liked. Equally well known is the fact that one of the epigrams was likely included as an inscription in Costa’s (now unidentified or lost) painting, but the texts had not previously been located. The article then contextualizes these rediscovered poems, relating them to the literary and artistic culture that flourished around the marquise of Mantua.