This dissertation explores the aesthetics and ethics of attempts to formalize and coordinate modern-i.e., disenchanted, antagonistic, contingent-understandings of the self and the social, the sexual and the political. In Part One, "Coordinating Private and Public Contingencies," I delineate an intellectual genealogy of attempts by cultural and social theorists to account for a modern recognition of the self and society as both riven by innate internal antagonisms and both subject to anarchic contingencies in development. I focus on Marx's and Baudelaire's resonant reflections on the popular failure of the 1848 revolution in France, and sketch an ensuing aesthetic-theoretical tradition of reading literary forms as cognate with and offering insights into the ideological totalizations of social and political forms. In Part Two, "The Resistance to Contingency," I critique the content and critical reception of Walter Benjamin's highly influential dismissals, on supposedly progressive political grounds, of Baudelaire's aesthetic and ethical insights, grounding my analysis in a comparative reading of Benjamin's transcendental historical schemas in his political work against Baudelaire's decidedly immanent ones in his lyrics. In Part Three, "Contingency and/as Liberty," I explore this congruence of political and literary aesthetics further in an analysis of three George Orwell novels. I develop an argument about how the critical reception of these novels has not consistently considered their narrative structures' insinuation that conceptualizations and formalizations of the domestic decisively condition and constrain those of the political. In the conclusion, "Modernity, not 'Modernism, '" I offer an argument about the need to think of a literary "modernity" more capacious than the conventional confines of literary "modernism" by juxtaposing the "high modernist" Virginia Woolf's Three Guineas with a text of the Weimar-era legal theorist Carl Schmitt. I bring out their shared recognition of innate interpersonal antagonisms and their shared concern for the unprogrammable contingencies of political developments, but note their strikingly contrasting accounts of responsible decision-making given such awareness. Against Schmitt's aporetic distinction of an organic community of friends, I expound Woolf's more trenchant ethical vision of political community, one grounded in her less idealistic vision of domestic politics.