Based on paradigms in feminist theory and criticism, I conduct an analysis of two iconic works of twentieth century American feminist literature. Examining Herland (1915) by Charlotte Perkins Gilman and Rubyfruit Jungle (1973) by Rita Mae Brown, I assess their place within the canon of feminist literature--a canon traditionally thought of as Western. I cyclically explore how this canon parallels movements and institutions in actual feminism, and where the pitfalls in both can be traced. Due to the large span of time betwixt the two novels, I engage the historical progression American women experienced in the twentieth century and pair it with the progress feminist literature was likewise experiencing. Exploring the consequences of depicting women as people rather than male counterparts or others, I analyze the roles of the male gaze, male-less spaces, utopias, construction of female identity, motherhood, and how these culminate in feminine and sexual liberation. Utilizing philosophy from Christine de Pizan’s The Book of the City of Ladies and Simone de Beauvoir’s The Second Sex, I trace the origins of the male gaze and male-less spaces in literature and film and how women are essentially othered. I further employ the criticism of Adrienne Rich’s essay “Compulsory Heterosexuality and Lesbian Existence” to explore the roles of motherhood and heterosexual norms specifically. My findings deride the authors for their inability to construct legitimately liberated female protagonists. However, I simultaneously offer deference to the authors for engaging the tools and concepts they had available to them at the time in the interest of crafting powerful feminist narratives. I center on the claim that male-less spaces are difficult to fully as well accurately portray in literature, but the authors attempt to do so to move towards a liberation of women and should be lauded for the contributions they made.