In June 2013, a series of large demonstrations throughout Brazil started to shake its main cities and political landscape. In this article I juxtapose these protests, the social movements of the 1970s and 1980s that brought the poor peripheries of São Paulo to the center of the political scene, and the cultural production coming from these peripheries after the 1990s. This juxtaposition creates a perspective from which to look at the changes that have transformed cities, citizens, and the polity in Brazil during the last decades. One of my main arguments is that in São Paulo, as in many other metropolises shaped by peripheral urbanization, political agency is inseparable from the spatial configuration of the city and from its shifting patterns of spatial segregation and social inequality. I focus on the peripheries and argue that the quality of both poverty, the urban environment, and citizens’ engagement have changed a great deal from the 1970s to the present. Poverty has different signifiers in a city of better infrastructure, mass communication, democracy, less violence, and broader access to consumption. Difficulty in moving around the city is one of these signifiers. Moreover, politics has other languages and tools in the context of intensified cultural production and circulation and of a democracy people can take for granted.