This volume presents a comprehensive, inter-disciplinary re-evaluation of Hofmannsthal’s most successful play and, more widely, on his contribution to literary modernity and its aftermath. Der Schwierige marks Hofmannsthal’s attempt to depict and overcome the language crisis he himself recognized in the ‘Letter’ to Lord Chandos. Written between 1909 and 1920, the play reflects Hofmannsthal’s experience of the atrocities of war, unnameable but constantly present behind the chatter in the Viennese salons. The volume looks at the relationship between poetological and poetic texts, and sheds new light on the position of Der Schwierige in Hofmannsthal’s work. Contributions address central motifs of the play (community, identity, gender) as well as the way in which it positions itself as a tragic comedy after the end of a catastrophic war. Translations into other languages, its performance on stage and on screen, philosophical reception, and Hofmannsthal’s reaction to the downfall of the Habsburg Empire and his views on the role of marriage, are recurrent themes that are investigated from various perspectives.