Using a comparative and transnational framework, this paper examines similarities in the urban planning strategies adopted by Athens and Beijing throughout the twentieth century, as the two historic cities transitioned to modernity. It demonstrates the ways in which the ambitious centralized planning efforts of both cities largely failed to create functional, habitable urban environments, instead often resulting in unsafe or unlivable conditions for the majority of their inhabitants. It argues that the planning strategies of the two cities were driven by the desire to generate "symbolic images" (Lynch) that carry historic and political meanings. However, this process was complicated by conflicts and collusions between governmental and market forces, leading to a contradiction between the cities' symbolic images and their physical forms.