This dissertation argues that Russia’s confrontation with modernity generated a series of sociocultural paradigm crises that gave rise to a modernist grotesque aesthetic tradition, uniting over forty years of artistic production into a coherent literary movement. While close reading the work of Fyodor Sologub (The Petty Demon [Мелкий бес]), Andrei Bely (Petersburg [Петербург]), Evgenii Zamyatin (At World’s End [На куличках]), and Velimir Khlebnikov (“The Crane” [Журавль]), I argue that prerevolutionary modernist writers utilized grotesque modes of representation to depict a world where the former cornerstones of pre-modern Russian identity are fracturing under the pressures of modernity. In contrast to extant scholarship, I argue the 1917 Revolution is not a fundamental break in Russia’s experience of the crisis of modernity, but an extension, and an exacerbation of it. Though discourses of Russian identity formation will be rapidly recodified around the Soviet project, the same underlying grotesque aesthetic devices used by pre-revolutionary authors are taken up by a new generation of Soviet-era modernists. Mikhail Zoshchenko’s parody in Michel Sinyagin (Мишель Синягин) elicits skepticism about yesterday’s unenlightened masses becoming today’s new Tolstoys. Andrei Platonov’s anomalous depictions of the Russian periphery in his Juvenile Sea (Ювенильное море) are still inhabited by monsters, too far from Soviet nodes of power to be assimilated into the national ideological project. And Konstantin Vaginov (in the novel Goat Song [Козлиная песнь]) and Evgenii Shvarts (in the play The Shadow [Тень]) capture the prevalence of superfluous intellectuals with ruptured psyches, frustrated by their unsuccessful attempts to adapt to the new Soviet reality.