This book describes the development of the literary riddle in Renaissance Italy, when poets appropriated riddles from oral tradition, combined them with the conventions of literature, and paired them with solutions that could be checked after reading. The book includes an original theoretical framework for the investigation of riddles, dividing riddles into categories based on their enigmatic link. A section about the social uses of riddles in early modern Italy shows how riddles were routinely exchanged at soirees and in the activities of academies and congreghe, all environments where the folk qualities of the riddle could be playful appreciated. The riddle became a key element in narrative works by Giovan Francesco Straparola and Ascanio de’ Mori, and, for the first time, it fueled enough collections of poems to trigger an entire genre. Examples will come from Angelo Cenni, Daphne di Piazza, Girolamo Musici, Tomaso Stigliani, Giulio Cesare Croce, Antonio Malatesti, and many others.