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This article is an exploration of the political satire of Shimen Dzigan and Yisroel Shumacher and traces the careers of these two comedy superstars in Poland before the war and then in Israel, thereafter. It places them in the context of the history of Jewish entertainment and makes a particular claim for the innovative nature of Yiddish comedy, namely that it was an entirely modern form of Jewish expression. Dzigan and Shumacher performed in what was called in Poland, literary cabaret. It emphasized politics and current events and in the case of Yiddish cabaret, internal Jewish politics and the subject of antisemitism. Once in Israel the comedy duo continued in this vein, proving to be astute observers of local politics and watchdogs, of sorts, closely eyeing the country’s political and bureaucratic culture. After their split in 1960, Dzigan continued to perform solo to huge audiences until his death in 1980. Whether together with Shumacher or alone, exquisitely crafted sketches and monologues were of a Kafkaesque nature, the subject often being the absurdity of bureaucracies and the powerlessness of the average person in the face of them. Particular emphasis is given to Yiddish, the language in which Dzigan and Shumacher performed, and the particular qualities of their Lodzer dialect of Yiddish. The article then reflects upon the place of Yiddish in the Yishuv and the early years of Israeli statehood and addresses the particular troubles that confronted the Yiddish performer, given the official rejection of the language by the new, Hebrew nation.