This article aims to examine theatrical practice and music events in Macedonia (within the geographical boundaries of the kingdom until the Roman conquest) based on literary, epigraphic and archaeological evidence. The general conclusion is that, besides local music and dance genres, which were directly connected to the religious ceremonies and the cult life of the kingdom, theatrical, literary and musical performances were held following Athenian practice. Especially, during the late Classical and early Hellenistic period, testimonies abound of musical and dramatic competitions in the context of festivals or victory celebrations, mostly due to royal policy. Performances of Euripides’ tragedies and New Comedy plays are widespread; musicians and actors of various specialties, poets and encomium writers, mimes, buffoons, dancers and other “paratheatrical” artists, show off their skills to all the large Greek-speaking cities and offer entertainment at symposia or feasts, at private or public gatherings.