This work studies two medieval translations of Aesop's fables, one in Latin (1497) and one in vernacular Italian (1526), with a close examination of how each translation reflected its audience and its translator. It offers close readings of the "Feast of Tongues" along with six fables common to both texts: "The House Mouse and the Field Mouse," "The Lion and the Mouse," "The Nightingale and the Sparrow Hawk," "The Wolf and the Lamb," "The Fly and the Ant," and "The Donkey and the Lap-Dog." The selected fables highlight imbalances of power, different stations in life, and the central question of "how shall we live?"