When analyzing the early modern dramatic canon, power and dominance often are viewed as masculine traits. Most men have the powerful position of the household and women serve to be their subservient wives. However, Shakespeare enjoys putting pressure of this notion in many of his dramas. Working to break the demeaning mold of women, he tends to situate female characters in such a way that challenges the social norms of the time. Specifically, looking at the world through Cleopatra’s eyes, she completely confronts societal expectations, as her behavior in Shakespeare’s play challenges early modern gender normativity. The best way to acknowledge this gender role swapping of sorts is to analyze the texts from which Shakespeare obtained these ideas. In the following essay, I will seek to expand on the elements that break gender expectation in literature, specifically utilizing the contents of works that somehow inspired or compliment Shakespeare’s Antony and Cleopatra. Using Cleopatra and Antony as the main characters to analyze, I will use the work of Plutarch and Milton to survey the themes of temptation and female dominance. I will then further examine these feminist ideals through a close reading of a passage from Shakespeare’s Antony and Cleopatra. The conclusion of this piece will take the literary analysis and close reading into account as a pair to justify an analysis of Cleopatra’s more masculine stance seen throughout Shakespeare’s work.