Over the last decade, we have witnessed the emergence of an academic debate surrounding the relationship between youth and the 'new media', with a particular emphasis on the social uses of different digital technologies within the sphere of youth activity. A specific area of research has been dedicated to studying the use of digital media in the context of the so-called youth subcultures. With this article we expect to contribute to this ongoing debate, by examining the problem through an analysis of two interconnected case studies: protest rap and illegal graffiti. Both cases may be defined as subcultures, insofar as they are characterized as alternative, subterranean, and to a certain extent, subversive movements. The empirical ground for this discussion is based on several investigations, with a qualitative basis, carried out by the authors in the course of over a decade in Portugal. This extended time frame allowed ample access to a diversified and matured analytical material and enabled a better perspective of the developments and the mutations involving the appropriation of the digital media. Our researches have shown that digital media and technologies have been gradually integrated in these urban youth subcultures, accomplishing several strategic roles.