This dissertation offers a select history of the literary portrait genre in Russian culture from its genesis in the 1890s through the 1960s. I define the literary portrait as a succinct account of a particular author's individual or creative personality – in Russian, lichnost' – that readily lends itself to anthologization, in which that literary portrait acquires additional meaning through the comparative or cumulative format in which it participates. In tracing the developments in the genre through a series of representative portrait collections, I focus in particular on two historical moments: 1905-1914, when literary portraiture moved beyond its original Symbolist confines, courted a wider reading audience, and became a key genre for the theorization and explication of Russian modernity; and the post-Revolutionary period, when writers both in emigration and within the Soviet Union repeatedly turned to the genre as a means of shaping narratives about late imperial and early Soviet culture. In the first period, I consider the literary critical portraiture of Iulii Aikhenval'd, Kornei Chukovskii, and Maksimilian Voloshin, and in the second, I consider the memoir-portraits of Vladislav Khodasevich, Kornei Chukovskii, and Iurii Annenkov, as well as Annenkov's work in visual portraiture. I posit that these writers, each in their own way and to their own ends, sought common variables that would unite the heterogeneous literary field of late imperial Russia. In doing so, they created forms of literary historical periodization that focused on cultural continuity rather than aesthetic displacement, and on webs of connections between individual authors rather than distinctions between nominally antithetical movements. These holistic interpretations of late imperial Russian literature demonstrate the pedagogical utility of comparative frameworks that take individuals (lichnostoi) as their units of observation. In constructing such frameworks, these portraitists consistently demonstrate that our understanding of dominant aesthetic movements of the time (the Symbolists and Modernists) and the dominant paradigm of cultural periodization that followed it (the Silver Age) are best calibrated against certain figures (especially Leonid Andreev and Maksim Gor'kii) who are otherwise afforded narrow parts in our inherited literary histories. Thus, I aspire to present literary portraiture as a telling artifact of Russian modernity writ large, and a valuable means of re-examining the literary historical narratives that structure our study of early twentieth-century Russian culture.