A comparison of Vienna and Berlin, the two most significant centres of German-speaking decadence, provides insight into the relationship of social class and aesthetic experience in the waning years of the Austro-Hungarian Empire (1897–1914) prior to World War I and during the tumultuous period of the Weimar Republic (1919–1933). The cultural and urban development of both cities, in their shared departure from nineteenth-century certainties, qualifies them for comparison in the context of decadence: Vienna’s imperial decline clashed with a radical re-thinking of tradition in art, and Berlin’s expressionistic distortions brought forth a brutal modernity that conservative thinkers considered to be the expression of racial degeneracy. To show how social history shaped the aesthetics of decadence at the time, the chapter focuses on the decadent art and writing of Gustav Klimt, Sigmund Freud, and Arthur Schnitzler in Vienna, followed by Otto Dix, Alfred Döblin, and Christopher Isherwood in Berlin.