Universal Introduction: When subject to cultural hegemonies build on race, xenophobia, and misogyny, individuals are focused to temper and suppress their authentic selves. Shakespeare’s Jacobean tragedy Othello and Tracy Chevalier’s contemporary appropriation New Boy both utilise their protagonist’s conformity to ethnocentric proclivities to indicate one’s inherent ability to internalise racial ‘Othering’. Further, the authors broadly similar stance on the objectification of women, portrayed as ‘possessions’, whilst projecting the deuteragonist as defiant to their contextual expectations demonstrates how individuals can overcome their circumstance. As a result of their respective contexts, Chevalier’s New Boy offers a contemporary lens through which Othello is transformed, although both texts reveal and question ‘Othering’ which inspires widespread change in their societies nonetheless. Universal Conclusion: Ultimately, both Shakespeare’s Othello and Chevalier’s New Boy resonate across time in their message of experience as ‘outsiders’ originating from both societal impositions and one’s individual perception as difference. The 1606 tragedy examines the role of ethnocentrism in alienating Othello in Jacobean Europe, as well as the social constrictions placed on women forced them to temper their authentic selves. Whereas, the postmodern novel sees Osei similarly suffering from 1970s institutionalised racism, and insecurities that expedite his conformation, as well as the recontextualised social constraints of women and how one can overcome them.