This chapter examines how in Thomas Mann’s novel Lotte in Weimar the phenomenon of literary icons not only raises the question as to the relevancy of literature in the modern world but also influences the literary form of the novel. It is argued that the text not just reproduces cultural icons but that it presents them as cultural icons, making their iconicity and the process of iconization a subject in their own right. While repudiating iconic representation of reality as inadequate, the novel not only dedicates ample space to the depiction of iconization as a process, but also adapts the very techniques of iconization in its own literary form. In its treatment of cultural icons, the novel pursues three goals: Firstly, it presents cultural icons as an integral part of popular culture and the formation of collective identities, thereby acknowledging their social and cultural relevance. Secondly, it seeks to support the notion of a gap between high culture and popular culture in that it suggests that iconic representation is inferior to those modes of representation cultivated in high art. Thirdly, it utilizes cultural icons and techniques of iconization as material for poetic transformation in order to poetically represent its author’s idea of the essence of human experience of time and identity.