Cultural landscapes are shaped by a combination of social forces. In some cases, one or a few powerful actors can impose their wills on a landscape; such top-down processes are found behind, e.g., Haussmann’s Paris or Eisenhower’s Interstate Highway system. In other cases, landscapes form by cumulative but uncoordinated actions by many individuals. Such emergent landscapes could be highly complex, despite their lack of central planning. In northern Mesopotamia, the landscapes of the earliest cities of Early Bronze Age (ca. 2600-2000 BC) and the Assyrian Empire of the Iron Age (ca. 900-600 BC) were both highly structured. Using case studies in remote sensing and field survey from Syria and Iraq, this presentation argues emergent EBA landscapes were replaced by centralized imperial landscapes in the Iron Age. It concludes that the landscapes of the earliest states took their form with very limited centralized manipulation, but political realities caught up with royal rhetoric by the time of the Assyrian kings. More generally, archaeologists must be careful not to assume the hand of central planners behind structural regularities in the archaeological record of cities and their landscapes.