A vast collection of small terracotta masks is on show in an imaginative display in the Aeolian Archaeological Museum, Lipari, Sicily. They are dated between the first half of the fourth and the middle of the third century BC, or to be more precise, 252 BC, the year the area was conquered and destroyed by the Romans. Discovered in the area of the necropolis at Lipari in the early 50’s, these theatrical masks are associated with both tragedy and comedy, and are unique for their attributes and for the manner in which they were made. Not only are they interesting from an archaeological point of view; they offer the oportunity to examine the role of theatre in the Hellenistic and Greek world. To this day, critical opinion has not been able to supply a convincing interpretation of their function. Two facts which have been neglected or not been sufficiently accounted for have formed the basis of this research, which aims to present a new interpretation. The first is the presence of a small hole on the occipital segment of all the small masks. The second is the interpretation of a passage in Pliny’s Natural History. A comparison between the technical information and the interpretation of the ancient source makes it possible to advance a new hermeneutical hypothesis that is consistent with the funerary context in which the objects were discovered. In the afterlife, Dionysus, the god of theatre, took care of the deceased who were followers of his mysteries. In the small theatre masks in Lipari, we have found a symbol of the double valence of Dionysus: the theatre as a place of dispossessing the self, of loss of identity in representation, and the realm of otherworldly delight, an arena in which the identity of Dionysus blends with that of Hades.