An interdisciplinary study of women satirists of the Progressive and Jazz eras, the dissertation investigates the ways in which early modernist writers use the satiric mode either as an elitist mask or as a site of resistance, confronts the theoretical limitations that have marginalized women satirists in the academic arena, and points to the destabilizing, democratic potential inherent in satiric discourse. In the first chapter, I introduce the concept of signifying caricature, an exaggerated characterization that carries with it broad social, political, and cultural critique. Edith Wharton uses a signifying caricature in The Custom of the Country where the popular press, middlebrow literature, and the democratization of language is under attack. Several of Wharton’s satiric stories also ridicule the New Woman, revealing Wharton’s anxiety over women functioning in the public arena. The second chapter features recovery work of May Isabel Fisk, an internationally known comic monologist whose work has been lost to scholars. This chapter examines Fisk’s monologues, paying particular attention to her use of the eiron and alazon comic figures. The dissertation then moves on to Dorothy Parker’s biting satires of Jazz era decadence, the sexual double standard, and the oppressive norms of feminine beauty promoted in mass culture. The study concludes with an analysis of Jessie Fauset’s Comedy: American Style, a novel using a signifying caricature to chastise America’s failed racial policies and an essentialist theory of race. Comedy: American Style is an overlooked Depression era satire that challenges notions of a fixed American cultural nationalism even as it presages the idea of race as a floating signifier.