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This paper argues that the ‘city’ as a political entity is significant in struggles over the ‘urban’, by identifying two moments of ‘differential urbanization’ in the Middle East. Our study in Iran and Palestine/Israel shows that the vision of the ‘city’ as a legitimizing space for political citizenship is at the heart of conflicting imaginaries: in Iran, ‘cities of revolution’ built through housing the poor around Tehran, and redistributive politics that stand on filling the ‘rural/urban gap’, and in Palestine, the new city of Rawabi as a city of Palestinian independence, where privatized urban development contrasts colonial spatialities with anti-colonial potentials. Thus, the right to the ‘urban’ involves claims for the ‘city’ that go beyond the capitalist logic of urbanization. This theorization points to a troubling gap in the planetary urbanization thesis, which moves from collapsing the ‘urban/non-urban’ divide into ‘concentrated’, extended’ and ‘differential’ urbanization to diminishing the role of distinct sociospatial configurations in claims over the ‘urban’. Our case studies show that examining the reconfiguration of inherited spatialities in the context of particular political regimes is imperative for epistemology of the ‘urban’ in its planetary stage. Urbanization otherwise remains an uninterrupted process towards a non-spatial ‘urban condition’.