This paper compares the methods by which two prominent Syrian playwrights, Saʿdallah Wannūs and Muḥammad al-Maghūṭ, revolutionized and politicized Arab theatre in the second half of the twentieth century. Examining topics such as the Nakba of 1948, the Six-Day War of 1967, the continuous failures of the Arab Nationalist regimes, and the oppressions and disillusionment faced by Arab citizens, Wannūs and al-Maghūṭ take radically different approaches--serious drama in the former and satire in the latter--in an effort to speak truth to power and shock their audiences out of their political stupor. Wannūs’ play, “A Soiree for the Fifth of June” (1968), is a mise en abyme representing a performance of a play in the aftermath of the 1967 war, thereby allowing the playwright to question the role and function of theatre amidst tragedy and defeat. Conversely, al- Maghūṭ’s play, “Cheers, Homeland!” (1978), uses the overarching premise of a radio broadcast to present tragicomic vignettes that showcase the devastating consequences of dictatorship and tyranny on human life. While Wannūs has been hailed as the most prominent Arab playwright and his work extensively studied in Western scholarship, al- Maghūṭ’s popular satirical plays have been mostly ignored in favor of his ground-breaking contributions to the genre of prose poetry. This paper, however, puts these contemporaries in conversation with each other in order to examine how each playwright employed Brechtian alienation, navigated writing under the censorship of the Baʿthist regime, utilized the political potential of performance to question ideology, and critiqued the political and cultural malaise of Syrian society.