This article demonstrates the social and cultural significance of eighteenth and nineteenth century Dutch penny prints – one of the first mass media in European history. By using a combination of media and cultural historical approaches (Henry Jenkins, John Fiske) and an anthropological perspective (Eric Hobsbawm) it asserts that, contrary to common notion, penny prints were not just part of a commercialized, conformist mass culture, but existed as a form of social resistance and protest as well. This new insight is based on the analysis of the adaption and publication history of the eighteenth-century French criminal hero Louis Dominique de Cartouche, the equivalent of the English highwayman. Give the multiple, multilingual representations of this narrative – in pamphlets, songs, biographies, prints, paintings and movies – the pervasiveness of Cartouche can be regarded as a remarkable cultural phenomenon. This interdisciplinary and long-term analysis also demonstrates that popularization processes were more dynamic and multifaceted than often perceived. In the case of penny prints about Cartouche more conformist periods alternated with more rebellious periods.