Benjamin wrote one of the most influential and earliest theorizations of modernity in his critical writings on modern art and in his posthumously published The Arcades Project (1940). Benjamin’s project is to write Parisian nineteenth-century history as an Ur-history of the urban civilization of bourgeois capitalism. While Benjamin sought to produce a history of modernity out of the material culture of the nineteenth-century Paris, Tanp?nar in Five Cities (1946) tried to sketch out social, cultural and historical setting of five Turkish cities. In this sequence of essays combining travel writing, memoir, public historiography and fiction, Tanp?nar draws on the Seljuk and Ottoman imperial past in an effort to create a vision of Turkish history. However, rather than recollecting a dead past to reach an identiterian unity in the present, the forgotten and repressed aspects of the past haunts the present with its ultimate difference and distance. This paper aims to explore the parallels in these two texts in their direct or unintentional questioning of modern illusions such as cultural myths of progress, of historical causality, of a sanctified tradition and of a dead past. Benjamin and Tanp?nar sought to map a cultural history of modernity out of urban life and landscape in very different historical and cultural contexts. They tried to establish a different relation of the present to the past that overcame binaries of modern and tradition, past and present- a dialectical endeavor that eventually proves to be incomplete. Nergis Erturk recently argued for the urgency of brining these Tanp?nar and Benjamin together as critics and writers of melancholia of modernism’s fallen languages. In different ways, the writings of both have shaped the way modernism and modernity are perceived today in their respective communities. Tanp?nar’s literary and critical practices complicate issues of tradition, novelty and memory, which lie at the heart of the experience and the culture of modernity as theorized by Benjamin. Drawing on Bes Sehir and Arcades, this paper explores their expression of the inability of the modern subject to experience in the old, true sense of the term and how they live in a present of successive and regular intervals, cut off from past and future.