Tuqus al-Isharat wa-l-Tahawwulat, one of the last major plays by the Syrian Sa'dallah Wannus, published in 1994, is one of the most innovative plays from the Arab world in the twentieth century. Based on a historical incident, it dramatizes the story of the fall of the Naqib of Damascus when he is arrested with his mistress Warda. The Naqib's enemy, the Mufti, saves him from disgrace by substituting the Naqib's wife, Mu'mina, for Warda, although Mu'mina leaves the Naqib and becomes a notorious prostitute. The play also overtly treats male homosexuality. Previous analyses of Wannus's plays have focused on the influence of Brecht and the Thousand and One Nights, and criticism of this play's feminist theme. This article argues that much of the play's novelty and aesthetic power derive from aspects of Shakespeare, principally Measure for Measure, and from motifs, lexicon and ritual theatricality derived from Sufism as aesthetic form and religious practice.