My dissertation examines the reconfiguration of urban order in Belgrade and Sofia from the mid-nineteenth century to the eve of the Balkan Wars. I examine varied urban practices and spatial forms, from city planning to prostitution, taverns to prisons, in order to sketch out a set of processes which characterized the functioning of the modern (Balkan) city. Through a comparative approach that stresses the transnational nature of urban transformation in the post-Ottoman period, I look at the "Westernization" of the cityscape, the adoption of anthropometric measures against criminals, and the employment of public health to manage populations. I find these to be mutually-constitutive components that framed the experience of city life during the second half of the long nineteenth century. In the post-Ottoman processes of reconfiguration in Bulgaria and Serbia, Sofia and Belgrade became centers of a political ecology much larger than the imagined national space. The management of space and population, the basic tool of the modern state, was an urban set of skills, both cities a microcosm of state power. Likewise, it reformed old spaces of transgression, such as taverns, and engendered new subversive strategies - the wide-spread changing of identity, the proliferation of con-artists, swindlers, and cafe-chantant singers. By looking at the modernization of two Balkan cities, I argue that the global phenomenon of urbanism was more than the cumulative actions of hegemonic, Westernized elites pretending towards imagined national or bourgeois cultures. Rather, it was constituted precisely through the tensions of their relationship with various marginalized groups, a continuous production of a new, distinctly urban world.