Vladimir Nabokov’s New England ‘nymphet’ and Ivan Gončarov’s lethargic Russian landowner: focusing on this mismatched—and, for that very reason, enlightening—tandem, this article explores some crucial aspects of literary iconicity between transfictionality, transmediality, and transculturality. As “fluctuating characters” (U. Eco), having completed the process of “transfictional emancipation” (R. Saint-Gelais) from their source texts, Lolita and Oblomov—now also generic terms, internationally identifiable and quotable icons associated with the corresponding concepts—no longer just refer to Nabokov’s and Gončarov’s eponymous protagonists, but to palimpsestic cultural figurations. Both have inspired multiple rewritings and adaptations; they also enjoy considerable iconic presence in contemporary popular and everyday material culture. Beyond an all-too-simple dichotomy of (so-called) high and popular culture, both examples illustrate that iconization does not necessarily imply semantic simplification; rather, condensing manifold facets of meaning, these icons subsequently re-unfold in various frames of reference, possibly enriching our comprehension of the source texts. Revisiting Lolita’s and Oblomov’s reception history across different media and cultures, this article also examines the dynamics and chronology of icono-genesis: under which circumstances—in a combination of textual and contextual factors, socio-cultural premises and aesthetic devices—can literary characters metamorphose into icons, sometimes far beyond their original cultural context?