A search for an ideal remains an existential dilemma in the socio-cultural landscape of post-Soviet Russia. The collapse of meta-narrative of communism has called politically and culturally defined identities into crisis, while simultaneously opening up spaces for new identities to be negotiated and created. As Russians grapple with the effects of the USSR collapse on present subjectivities and socio-political contexts, the question of which voices will dominate contemporary national culture and what ideals will be integrated into the emerging national landscape has been confronted by Russian writers and film directors. In today’s Russian society of contradictory cultural legacy and renegotiated borders of national identity, both literature and cinema occupy a specific representational space between arts and politics. The most recent and interesting examples of this positioning are, for instance, the massively popular Russian films by Alexey Balabanov Brat (The Brother, 1997) and Brat-2 (The Brother–2, 2000), Nezhnyi vozrast (Tender Age, 2000) by Sergey Solovyev, and Pokhititeli knig (Book Stealers, 2004) by Ilya Lagutenko, or the novels by Darya Dontsova, Viktor Pelevin, and Boris Akunin determined to revise and understand the national experience of the 1990s and early 2000s. Historically, this period has put enormous pressure on all living generations in Russia, where questioning the existing geographical and cultural boundaries has defined Russia’s social context. The pressing concern is how artists give space to new voices as they move through the early post-Soviet experience to understanding new ways-of-being. Answering these questions requires a revisiting of a national culture at the turn of the twenty-first century in the search of new ideals for the Russian cultural Olympus and of ways those ideals have shaped, and continue to shape a new national idea. The paper highlights the new meanings Russian artists have attached to classical ideal literary types when attempting to re-construct cultural discourse on nation and nationalism in today’s Russia. The paper argues that the appearance of such works points at the emerging discourse on national identity situated within the Russia’s present. Central to the argument here is the idea that the process of rethinking both the cultural and the political in contemporary Russian fiction and films has advanced an essentially national conception of identity. At the moment, however, the conceptualization of new versions of the national in Russian culture does remain highly problematic. The paper presents a typology of “Heroes of Our Time,” and concludes with a discussion of a dramatic effect of a new concept of the national on literary and cinematographic representations of new ideal societal types within the rapidly changing canon of the post-Soviet Russian culture.