Few people know the true origins of Domenico Modugno. Most believe he was originally from Polignano a Mare, where he was actually born. Others even believe he was Sicilian, due to a misunderstanding dating back to the early 1950s involving Frank Sinatra and the Salento dialect, which is very similar to Sicilian. This misunderstanding was never clarified by the person concerned, who, partly for reasons of convenience, remained Sicilian for a long time, at least until his victory at the Sanremo Music Festival in 1958, when, becoming Mr. Volare, he radically changed the music landscape in Italy and abroad. It is therefore worth delving into his origins, recalling the historical and cultural context in which the young Modugno nurtured his creative streak, so as to trace the cultural and linguistic connections that later took shape in his artistic output. The starting point for this work is a varied collection of material, including recent publications and newspaper clippings from the period, private photographs, and precious oral histories rediscovered by those who lived with him during the postwar years in a small town in northern Salento, the same town he left to go to Rome and fulfill his dream of becoming an actor.