This essay examines skateboarding as an architectural act of pleasure that allows private spaces in cities to be appropriated for alternative uses. In particular, the appropriation of swimming pools by skateboarders will be explored, from the renegade to the officially sanctioned, to explore socio-political aspects of space. The film Dogtown and Z-Boys (Stacy Peralta, 2001) provides a primary source for this examination, and will be used as a vehicle through which to examine these issues, particularly in Los Angeles. Recent appropriations of swimming pools in New York will provide a secondary reference. In Dogtown and Z-Boys, swimming pools form a playground in which skaters in 1970s Los Angeles re-appropriated urban space for their own use. This paper will argue that the appropriation of swimming pools by skateboarders has provided a viable venue for alternative uses of the city that include both play and dissent. By framing the history of swimming pools in late 20 th century America, a case will be presented for how skateboarders’ appropriation of swimming pools in 1970s Los Angeles can provide clues to continual opportunities for alternative configurations and uses of twenty-first century urban space.