The second half of the nineteenth century witnessed significant novelties in the literary scene of Istanbul, the capital of a dissolving empire, mostly as a reflection of the more inclusive attempts at societal change. Namik Kemal, a highly prominent figure of this period’s intelligentsia, actively participated in the debates on cultural transformation and gave in-depth thought on the direction Turkish literature should take. His oeuvre, as a result, mirrors the confusions, anxieties, and self-questioning pertaining to Tanzimat (Reformation) era intellectuals, who found themselves in a struggle to coalesce what can be called two different conditions of literary aesthetics, the novel and the Ottoman classical poetry being the two genres that constitute their respective main axes. This paper looks into the introductory chapter of Kemal’s renowned novel Intibah (Awakening, 1876) with an aim to comprehend the ways in which writers of the time, who have been mostly trained within the Ottoman classical tradition, were handling this relatively new state of literary being. It is indeed interesting to note that, in Intibah, Kemal more or less replicates the general narrative structures and allegorical reservoir of classical literature in order to emphasize its outdated status. However, while utilizing the very target of his criticism to overcome it and create a new (and more Westernized) literary environment he often falls back into a seemingly inevitable reproduction of what he disparages, oscillating between a eulogy of an antiquated past and a ridicule of a despised history. In its effort to make sense of this puzzlingly complicated state of mind, this paper consciously avoids recourse to the simplistic view of this transformation as the encounter of two unchanging literary traditions, separated through rigid binaries, such as East/West, old/new, or tradition/modernity. Rather, it recognizes the internal progression of both, as well as the historicity of their interaction, and reflects on the dynamics of interliterary influence, imitation and appropriation in relation to the text in hand. By looking at this text that is deemed to be representative of its context through theories of intertextuality, the paper in fact endeavors not only to formulate a sophisticated approach that would to justice to the complexity of similar Tanzimat texts, but also to set light on post-Republican and contemporary perceptions of Ottoman classical literature.