The city of São Paulo has been a source of inspiration for musicians of different generations. Important moments of its urban history were recorded in famous songs such as “Saudosa Maloca” and “Sampa”, which good examples. This paper focuses on the representations of the city found in RAP music, an African-American music style that was appropriated and reelaborated by the youth from the outskirts of São Paulo. It was possible to notice that as the rappers compose their music they build a dialogue which includes the urban changes which have occurred recently. I conclude that the images that they draw express a radical critique of the new status of urban segregation. Their denunciations are about the violence that affects them and that goes beyond the boundaries of the neighborhoods where they live and which makes evident the lack of democratization processes.