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The flat rooftop emerged as one of many new forms produced by industrial capitalism’s spatial reconfiguration of the landscape. Designed to accommodate increasing urban density around industrial and commercial centers, the flat rooftop is generally treated by capital as unproductive or unusable space. And yet, young people, the displaced, the homeless or hunted, through practices of informal (and illegal) occupation, transform the urban rooftop into what James Holston might call a territory of “insurgent citizenship.” The makeshift and malleable habitation of the uninhabitable demands that we consider the rooftop as a paraspace—an alternative simultaneous and superimposed space, a contested and deconstructed landscape sprawling across the city in unimaginable ways, constantly defying the false binary of habitable and inhabitable, of private and public, of visible and invisible. In this paper I argue that the flat rooftop, as a site of insurgent occupation, constitutes a complex material paraspace that suggests a relationship between paraspaces and fugitivity, particularly fugitivity as a set of practices that are at once diagnostic of, and resistant to, the material and ideological infrastructures of late capitalism. I will consider the possibilities and limits of paraspace as a site of fugitive practice through a reading of key texts, including the 1989 film Rooftops, about homeless teenagers who live atop abandoned tenement buildings, and artist Faith Ringgold’s popular 1991 children’s book Tar Beach. These works expose the intersections of race and class, and narratives of surveillance, gentrification, property, and resistance within the spaces of neoliberalism.