The purpose of this thesis is to analyze a sampling of Gloria Steinem's feminist rhetoric by way of "If Men Could Menstruate" (1978/1983) and "What If Freud Were Phyllis?" (1994). I use a historical-descriptive methodology, in which I situate each essay in terms of their historical contexts, and I closely analyze Steinem's rhetoric in light of each historical situation. I also examine "If Men Could Menstruate" and "What If Freud Were Phyllis?" in terms of their enduring contributions. Towards this end, I consider whether or not these essays are touchstones of feminist criticism, meaning that a text meets audience demands and stands the test of time. Focusing on these two essays is necessary because they are memorable, they have received popular acclaim, they function as a pair, and they transcend the boundaries of second wave feminism.