A series of interventions by young men are transforming public spaces in São Paulo, Brazil, and articulating anew the profound social inequalities that have always marked them. The new urban practices include graffiti, pixação (São Paulo’s style of tagging), and new modes of moving around the city (motorcycling, skateboarding, and parkour). They give young men from the peripheries a new visibility in the city and thus challenge previous understandings about the functioning of public spaces. However, these interventions are contradictory: they affirm rights to the city while fracturing the public; expose discrimination but refuse integration. They test the limits of the democratization process by simultaneously expanding the openness of the democratic public sphere while challenging it with transgressive actions ranging from the mildly illicit to the criminal.