In William Shakespeare’s Othello, we are introduced a man trapped between two worlds. Othello, an African Muslim-turned-Christian, lives among the Venetians, but can never truly become one of them. Centuries later, Sudanese writer Al-Tayeb Salih would use Othello as the inspiration for his own characters stuck at the crossroads between cultures; his narrator and the character of Mustafa Sa’eed in the novel Season of Migration to the North. Both works examine what it means to exist as a conduit between the East and West, Islam and Christianity, and ultimately, they establish a similar theme. I will argue that through each author’s unique approach to the subjects of otherness, self-hatred, exploitation, and choice, both Shakespeare’s Othello and Salih’s Season of Migration to the North demonstrate an inherent destructiveness of the conflicting cultural identity. Each work tells the story of Arab-African characters (i.e. Othello, Mustafa, and Salih’s narrator) who live among Europeans who believe that their cultures are inherently in conflict. As such, I will begin by showing how the characters of Othello and Mustafa are characterized as “the other” by Western-born characters. In the case of Othello, the eponymous character is constantly regarded verbally in terms of his otherness, despite his attempts to assimilate into Venetian culture. The Venetians refer to him constantly as “the Moor”(Shakespeare, 1.1.39), a word with Islamic connotations, even though he has converted