In recent years contemporary German popular music has received a fair amount of academic attention. However, the issue of its specifically German roots and origins has been largely neglected. For the most part German popular music is still regarded as an uninspired copy of American and British models. Aiming to redress this misperception, this article focuses on the chanson and cabaret culture of the Weimar era and its significance for the work of Udo Lindenberg. Lindenberg, one of the veterans of German popular music, has described himself as Marlene Dietrich’s ‘Enkel aus Berlin’ and as ‘Vermächtnisnehmer’ of the 1920s’ and 1930s’ chanson and cabaret culture. By exploring the legitimacy of this proud self–description, the article seeks to contribute to the study of German popular music and, more specifically, to show that the work of Udo Lindenberg deserves to be taken more seriously than it has been so far.