The history of Joseph Conrad’s Heart of Darkness has been one of adaptation and change. The enduring story is based upon Conrad’s experiences in the Congo in the 1890s and has been published as a novella in 1902. Since then the story has been criticised for racism by Nigerian writer Chinua Achebe (1975) and relocated to Vietnam by Francis Ford Coppola as Apocalypse Now (1979), influencing computer games such as Far Cry 2 (2008) and Spec Ops: The Line (2012). In examining the adaptations of Heart of Darkness we can consider how the story evolves from the passive reading of post-colonial narratives through to the active participation in morally ambiguous decisions and virtual war crimes through digital games: examining Conrad’s story as it has been adapted for other mediums provides a unique lens in which to view storytelling and retelling within the context of how we interpret the world. This paper compares the source material to its adaptations, considering the blending of historical fact and original fiction, the distortion of the original story for the purpose of creating new meaning, and reflects on whether interactivity impacts upon the feeling of immersion and sense of responsibility in audiences of different narratives.