Recent excavations and theoretical advances have revealed evidence of an early and perhaps independent nucleation and centralization process in the region south of the Alps, a phenomenon that has been undervalued in previous studies. In this paper I present a broad overview and attempt to reassess the role of the Cisalpine regions as crossroads of trade and cultural transfer between the Mediterranean and central Europe through a critical evaluation of key archaeological evidence. I adopt alternative and up-to-date perspectives on the urbanization phenomenon, disentangling commonsensical and text-driven definitions of urbanism and social formation, while challenging the outdated “check-list” approach. This theoretical framework should promote a paradigm shift that leads to a substantial backdating and broadening of the appearance of complex site agglomerations in northern Italy, avoiding unidirectional development patterns and instead looking at possible cases of instability, ephemerality, and seasonality. The adoption of a comparative perspective triggers a timely disentanglement of the simplistic equation between urbanism and social hierarchy. Beyond a narrow and selective emphasis on elites, this paper considers alternative social entities and actions, including commoners, subaltern groups, and cooperation.