In examining Malaysian literature in light of the global canon, one cannot miss the numerous parallelisms between literary works by Tunku Halim bin Tunku Abdullah and Edgar Allan Poe. Both writers are preoccupied with grotesque realities of mentally deranged individuals, and similarly visualize the darkness and animality of human consciousness. This article aims at conducting a comparative analysis of the dynamics of personality and of the psyche of fictional characters in selected short stories by the two writers. To this end, the study draws upon Jung’s notions of the Shadow and the Individuation to explore the key psychological motives behind the characters’ behaviour patterns, as well as to examine their level of subjectivity and agency in harnessing the same motives. Notwithstanding the seemingly different ways of presenting the narrative patterns of the characters’ journey towards Individuation, the selected stories are marked with similar examples of characters’ failures in the process of self-realization. While some characters remain trapped in the obscure and perplexing world of the Shadow, others achieve a minimal level of maturity as they begin to realize their own being. In the case of Halim’s stories, however, the characters are additionally held back by cultural and structural forces that constantly affect their realities. It is concluded that this particular difference accounts for Halim’s uniquely hybrid style of writing that merges Western horror genre with more local folklore.