According to legend, its particular form of a donkey ear made the painter Caravaggio, who traveled to the city of Arezzo in 1608 in the company of the historic Syracuse Vincenzo Mirabella, the expression Orecchio di Dionisio. According to tradition in fact the tyrant Dionysius had the cave dug where the prisoners were enclosing and, lurking inside an upper cavity, he listened to their speeches. Thanks to its shape, the Ear of Dionysus has acoustic characteristics such as to amplify sounds up to 16 times. 
According to the reconstructions of Eliano, Dionisio would have enclosed the poet Filosseno, with the fault of not appreciating the literary works of the tyrant, in this place or in the nearby "Grotta dei cordari". Eliano affirms in fact that the poet had been imprisoned: "in the most beautiful cave of the Latomie, where he had composed his masterpiece, the Cyclops: cave that later took his name".