This study presents a critical and textual analysis of John Gardener’s novel, Grendel. Relying heavily upon aspects of post structuralism, the study examines the two texts, Beowulf, an anonymous medieval epic, and John Gardener’s Grendel in terms of their contexts and discourses. The study argues that Grendel is a hypertext that relates to Beowulf by means of transtextualty so as to tackle crucial perspectives of western philosophy, civilizational heritage and thus elucidates its existential discourse. The study concludes that Gardener’s novel is a revisionist narrative that aims at elaborating on the concept of heroic Self as opposed to the antiheroic ‘Other’. Further, the study concludes that Gardener’s, by means of adaptation, presents a new discourse that does not reduce Grendel, the monster in the original epic, to the demonic stereotype of the ‘wronged villain’. The significance of the study springs from the need to liberate literature from the anxiety of aimless imitation and thus enhancing Derrida’s poststructuralist notion which confirms that meaning has no definite closure. The study significantly examines the texts with reference to Gerard Genette’s structural narratology, John Gardner’s The Art of Fiction, and other critics who theorized the main key concepts in intertextuality, appropriation, and adaptation.