In the historiographical accounts of Italian song between the World Wars, the impact of American jazz emerges as an important factor beyond the Italian national context. If we consider the complicated discourse of race and racial purity that was part of Italian nationalism of the period, the influence of American jazz, which is grounded in African American culture, is surprising to say the least—if not contradictory. Through the investigation of period magazines and sound documents, which display the controversial relationship between the Fascist regime and foreign music, this project presents a study that investigates the connection of stylistic and cultural/historical data with new musical analysis of the most prominent recordings of the interwar years.