This article offers a re-appraisal of the origins and evolution of holistic urban anthropological approaches, explaining how, why, and in what context these coalesced during the first quarter of the 20th century, as well as offering an explanation for the ensuing rise of more parochial approaches to city life. It does so based on an alternative intellectual history of the famous Chicago School of Sociology (CSS), in particular highlighting the epistemological debt contemporary anthropological studies implicitly owe to the CSS, as well as the enduring methodological lessons that the urban studies it inspired potentially continue to offer for anthropology.