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Georg Simmel (1858-1918) and Walter Benjamin (1892-1940) belonged to two successive generations of thinkers and cultural critics who formulated their ideas on the urban crowd and worked externally and internally, respectively, to the "short" twentieth century. Their points of view on the crowd as the typical social form of the modern metropolis represent two highly significant lines of thought in the history of the twentieth century, which at its beginning gave rise to a hope in the proliferation and flowering of individuality, but later deteriorated into the conventionalism of mass culture and the "colonization of consciousness" brought about by totalitarianism. The perspectives of these two thinkers on the question of the crowd stemmed, in Simmel's case, from a perspective before the crowd: a defense against the dangers that it represented for seventh-to-nineteenth-century individuality, whose dynamics are at the heart of his work. Benjamin, witnessing the impotence and inadequacy of the principium individuationis to withstand the reactionary regimes of the masses, would find in the waning of this principle, find hope—soon to be disappointed—for a new era of the masses and an ill-defined "new collective body" beyond the crowd.