In Jeffrey Eugenides' novel "Middlesex," the contrast between urban planning in culturally rich cities and industrial cities like Detroit is emphasized. While cities like Paris, London, and Rome are planned with cultural significance in mind, Detroit is portrayed as a city driven by financial motivations. This drives design choices to favor practicality over aesthetic considerations, leading to a more chaotic urban landscape.

Since its establishment in 1818, Detroit has developed alongside the river through a haphazard growth of warehouses and factories. The original vision of its planning, such as Judge Woodward's intentions, has been overridden by the realities of industrial expansion, resulting in a city that conforms to standard rectangular layouts, lacking the artistic touch found in more culturally oriented metropolises.