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This paper aims to analyze the nature of masculinity by comparing the works of three major writers of the Victorian period: Stevenson’s Treasure Island, Kipling’s Captains Courageous, and Conrad’s Heart of Darkness. This paper also attempts to compare these literary works with the film adaptations of them to gain a multi-faceted approach to the core issues of the depiction of masculinity. During the period, the imperial demand for nurturing manliness within the male-oriented society gives rise to the formation of the adventure novel. Corresponding to this demand, Stevenson and Kipling create a homosocial environment where males educate each other. Though the educational process is not unanimously plausible, the writers’ aim is fully accomplished in that readers are able to see adversities and hardship mature immature males in their narratives. By contrast, Conrad demonstrates a disappointing homosociality in Heart of Darkness, meticulously describing the protagonist’s emotional journey to his double as a complicated amalgam of such emotions as affection, admiration, abhorrence, and even jealousy to disclose the hollowness of the Victorian masculinity.