Die Frau ohne Schatten (The Woman without a Shadow, 1917) was conceived as Richard Strauss and Hugo von Hofmannsthal's ‘chief joint work’, and its central message has been read as an allegory of artistic collaboration and social engagement. This article calls upon Walter Benjamin's theory of allegory to enrich such an interpretation and unravel the opera's positive conclusion as an inadequate cure for the artistic melancholy of the fin de siècle. While Strauss successfully engaged with allegory to portray two of the opera's characters – the infertile Emperor and Empress – he was unable, for his own philosophical reasons expressed in the contemporaneous Eine Alpensinfonie (1915), to ratify Hofmannsthal's hope, rooted in his ‘Chandos Crisis’, of creating an aesthetic totality, of reconstituting the symbol that Benjamin, in his later writings, pits against allegory.