This chapter shows how, in late nineteenth- and early twentieth-century South America, intellectuals witnessed European and U.S. industrial progress, imperial power, and apparent cultural modernity, against which they compared their own nations, usually unfavorably. One major strain of national self-criticism focused on the supposed absence of a genuine bourgeois middle class or, if existent, its inability to carry out the “historical mission” attributed to its European counterpart. The diagnoses ranged from a focus, in midcentury, on the legacies of Spanish oppression, to more radical, materialist, nationalist, vanguardist, and anti-imperialist perspectives in the 1920s. Yet ideologically divergent explanations of middle-class failure often had common themes, many of which persisted into the 1970s and inspired both cultural and dependencia theories of Latin American underdevelopment that still echo today. Finding similar debates in Argentina, Chile, and Peru—countries whose economic and demographic fortunes varied considerably—the chapter shows that narratives of a missing or flawed bourgeoisie may have accurately reflected the knock-on effects of Latin America's successful insertion into the global economy.