By offering a historical reconstruction of the process of contextualisation of hip hop culture in Italy over the last fifteen years, the article assesses the current status of canzone d’autore and its changing configuration under the impact of rap music. From a theoretical point of view, the conceptual framework combines the sociological definition of ‘field of cultural production’ elaborated by Pierre Bourdieu with the related literature on social and symbolic boundaries. From a methodological point of view, the analysis is based on the data collected by Club Tenco (a cultural organisation which plays an institutional role within the field of canzone d’autore) as well as on a series of qualitative interviews carried out with a number of Italian rappers and cantautori. Special attention is paid to a very few crucial figures that can be considered paradigmatic examples in the dynamic process of boundary-making of the two cultural (sub-)fields of Italian rap and canzone d’autore.