People of all cultures experience liminal, or transitory, states. However, some subcultures exist almost exclusively in liminality. This work explores the protracted liminal state experienced by homeless men in Cleveland, Ohio. Many contemporary views of homelessness were established in the early part of the twentieth century, during the Great Depression. These views have given rise to a set of archetypes used to attempt to classify the perceived chaos of the liminal state. By comparing historical data with contemporary fieldwork, this work demonstrates how these archetypes have and haven't changed in the last seventy years, and gives a glimpse into the lives of some of those who live in the liminal.