This chapter explores the cultural and political crises of twentieth-century modernity through the lens of civility’s erosion amid the rise of mass society, totalitarianism, and technological manipulation. It begins with José Ortega y Gasset’s The Revolt of the Masses (1929), portraying the mass-man as a threat to liberal civilization through dissociation, loss of objective standards, and barbarism, destroying Ciceronian concordia and trampling real and intellectual aristocracy. The discussion extends to contemporary literary stars: Stefan Zweig’s The World of Yesterday (1942) nostalgically evokes pre-World War I Vienna’s cultured harmony and bourgeois refinement as antidotes to modern ugliness, while Evelyn Waugh’s Brideshead Revisited (1945) defends intellectual and traditional aristocracy and Catholic values against secular barbarity. The chapter then examines totalitarianism’s assault on civility, showing up in modernist architecture exemplified by Le Corbusier and Bauhaus, the aspiration of ideological control leading to urban destruction. Finally, it traces the spectatorial turn via photography, film, mass media, and digital culture, culminating in Debord’s society of the spectacle, narcissistic alienation (Lasch), and resonant disconnection (Rosa), alongside pop culture’s commodification of youth revolt, threatening democratic consensus and underscoring the enduring need for renewed civility.