Classical literature features numerous prominent female characters. This thesis paper identifies and examines the pattern of masculinization of female characters in classical literature through case studies of two characters and two authors. The character Iphigenia is examined as an example of a heroically masculinized female character and the character Agave is examined as an example of an aggressively masculinized female character. The mythologies of these two women are analyzed through the writings of the authors Euripides and Ovid in order to compare and contrast the perspectives of a Greek and Roman author on masculinization. The texts analyzed for this paper were Euripides' Iphigenia at Aulis, Iphigenia Among the Taurians, and The Bacchae, as well as Ovid's Metamorphoses. This paper also analyzes the responses to masculinized female characters within the texts and identifies patterns of re-feminization in Euripides' writing and dehumanization in Ovid's writing. These responses are found to be reflective of cultural values regarding gender and this paper discusses how these literary characterization patterns are indicative of cultural anxieties regarding gender norms. Finally, this paper briefly addresses similar patterns of masculinization in modern film and literature exemplified by the proverbial "strong female character." This paper compares two modern "strong female characters", Katniss Everdeen from The Hunger Games and the Bride from Kill Bill, to Iphigenia and Agave and draws parallels in their masculinization patterns. The results of this paper's textual analysis conclude that classical authors (as well as some modern authors) often masculinized their female characters but expressed subsequent cultural discomfort with those characters as a reflection of uncertainty regarding established gender norms.