The postcolonial urban landscape, especially in Africa, remains a place defined by an inchoate relationship between the different social classes occupying it. This essay is a brief analysis of the relationship between the poor and the rich in an urban setting as dramatized in popular literature from Kenya. The essay emphasizes the calculated strategies that the poor adopt, as underdogs, in the battle with the rich over resources . Such strategies have only one objective: to maximize benefits in any situation when an advantage can be extracted. Such tactics are adopted by either female or male characters, according to the literature that we refer to, more so because the gender divide further dramatizes the structural relationships of inequality between the different socioeconomic classes, but in this instance within the underprivileged class(es). But these tales are not just stories of “survival tactics” by the poor in urban Kenya. The tales also implicate the rest of the society as complicit in the production of the social realities that (re-)produce the melodramas enacted in them.