This chapter explores the intersection of globalization, digital technology, and contemporary Neapolitan music, focusing on the aesthetic and political implications of media transformation. Through a case study of the band Almamegretta, it examines how local musical traditions are reconfigured through global flows, digital tools, and hybrid cultural expressions. Drawing on theoretical frameworks from Walter Benjamin, Jonathan Crary, Paul Gilroy, and Toby Miller, the chapter interrogates how technological reproducibility reshapes perception, identity, and artistic agency. Almamegretta’s work exemplifies a form of ‘critical regionalism’ that resists both cultural homogenization and nostalgic essentialism. Their use of Neapolitan dialect, electronic music, and transnational collaborations challenges dominant narratives of Italian identity and reclaims space for Southern voices in global culture. The chapter argues that contemporary art, particularly in digital and musical forms, must be understood as a communicative and political practice that reflects and reshapes the conditions of globalization.