This thesis accompanies a modern-day adaptation of Shakespeare’s Twelfth Night, which aims to emphasize the importance of gender equality as a moral imperative in the twenty-first century. In his original play, Shakespeare drew attention to gender stereotypes in the Elizabethan age through character representation. Although Shakespeare does not put much emphasis on gender equality in Twelfth Night, this equality is an important factor in the modern adaptation, in which a young woman named Vivian pursues her desire to start a business but is faced with financial issues and seeks a job under a misogynistic boss named Owen. Owen questions her ability to succeed in the business world, but Vivian’s mature influence brings about a change in his perspective on gender roles as Vivian proves to be a strong, independent character. This thesis informs the adaptation by exploring gender roles in both the Elizabethan age and the twenty-first century to critique gender stereotypes and promote gender equality.