This paper seeks to reveal the identity crisis caused by the complicated racial and power relationships in English playwright William Shakespeare's Othello (1603) and Sudanese author Tayeb Salih’s Season of Migration to the North (1966) by analyzing the identity construction of the two black protagonists, Othello and Mustafa Sa’eed, from the perspective of postcolonialism. Main characters in both works are black men who are trying to make it in a predominantly white society and who are struggling to cope with the influence of white culture at both home and at work. Similarly, despite the fact that the cultural encounters occur in different locations, namely one in Venice and one in England, the white cultural characteristics are manifested in the stories with similar meanings and functions. Both Othello and Mustafa fail to convey an objective image of the black to the whites by responding to the whites’ presumptions in an effort to assimilate or exact revenge, neither of which are good starting points for the confrontation between blacks and whites. The failure of the protagonists’ attempts at intercultural communication suggests that assimilation, separation, and marginalization are not desirable in intercultural communication, and that identity negotiation requires more respect and understanding. Within this context, this study seeks to conduct a detailed textual analysis of the protagonists’ identity formation by examining their experiences in the racial interaction.