Caliban in William Shakespeare’s The Tempest and the unnamed narrator in Margaret Atwood’s Surfacing, both dwelling in an underpopulated island for quite some time, bear striking similarities, particularly when seen as two characters who have fallen victim to colonialism. This paper begins by comparing the modern exploitation in Surfacing and traditional colonizing practices in The Tempest. Afterward, it goes on to highlight the role Caliban’s and the Surfacing narrator’s fathers played in making the colonization of their children justified, so to speak. Then, this paper compares the way these two characters undergo transformation. Alongside elaborating on Caliban’s and Atwood’s unnamed narrator’s comparable temperaments, this paper will discuss the way these two characters come to negotiate the hegemony of imperialism. Employing the ideas of Homi Bhabha and Margaret Atwood regarding the third space/thing, this paper, in its conclusion, addresses the measures taken by these two characters to tackle the hegemonic power through compromise.