The proposed article addresses the phenomenon of the Viennese urban originals on the example of three personalities with official original status, special entourage, idiolect, idiokinesics and perlocutive impact on the Viennese and generally Austrian public. The aim of the paper is to investigate the Viennese originals’ fate during the National Socialist dictatorship after the “Anschluss” of Austria. The relevance of the article is connected to the development of the methodology of a new direction in Language and Culture Studies – Linguistic Portraiture that is regarded as a kind of archaeology of knowledge about real culturally significant personalities of specific countries. This direction differs from Linguistic Personology in its orientation: it is not aimed at generalizing cultural types reflected, first of all, in the phraseological fund of languages and their literary tradition, but at the study of dissipative groups encompassing personalities that can be regarded as living cultural phenomena, to which urban originals doubtlessly belong. The methods used in the article include systematization, classification, interpretative and contextual analysis, and metacritical analysis of biographical and scientific literature. The article speculates on the specificity of the discourses that took shape around Helmut Qualtinger, Beatrice Triangi and Karl Sesta, drawing on biographical materials, investigative journalism, works on linguocultural studies and texts produced by Viennese originals. The study is an attempt to reconstruct the intellectual discourse of the Austrian capital in the first half of the twentieth century.