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Throughout the 1920s and 1930s, first- and second-generation American Jewish writers and composers working in popular entertainment largely resisted the modernist despair so fashionable among many of their contemporaries, choosing instead to devote themselves to an optimistic set of truths promised by American liberalism and expressed in the theatre. By the late 1930s and early 1940s, however, the lingering Great Depression, rising anti-Semitism, fascism, and the Second World War led to the hollowing out of many of the ideals of the immigrant generation and their children. A number of Jewish writers, many of whom had made their reputations defining and celebrating an ideology defined in this essay as theatrical liberalism, began to echo their modernist contemporaries. Just as modernist poets and novelists experimented with form in order to raise questions about truth, so modernist writers of popular plays and movies used the heavily formulaic nature of their genres to shock audiences into questioning the assumptions of theatrical liberalism upon which these popular forms relied. This essay explores how Richard Rodgers and Lorenz Hart's 1940 musical Pal Joey uses the popular genre of the backstage musical to raise questions about the viability of theatrical liberalism in an era plagued by fascism, Nazism, and war.