The history of Joseph Conrad’s Heart of Darkness novella has been one of adaptation and change. The enduring story is based upon Conrad’s own experiences in the Congo in the 1880s and was serialised in Blackwood’s Magazine 1899. Published as a novella in 1902, since then the story has influenced T.S. Eliot to pen The Hollow Men (1925), roundly criticised for racism by Nigerian writer Chinua Achebe (1975), been relocated to Vietnam by Francis Ford Coppola as Apocalypse Now (1979), and adapted for a graphic novel by Catherine Anyango and David Mairowitz (2010). As Video Games have become popular channel of communicating stories Heart of Darkness has influenced Far Cry 2 (2008) and Spec Ops: The Line (2012). Examining Conrad’s story as it has been adopted, acquired and adapted for other mediums provides a unique lens in which to view storytelling and retelling within the context of how we interpret the world. Storytelling is an intrinsic part of society and culture but each story evolves in multiple forms and formats. Retellings (including a remake, reimagining or reboot) are naturally framed by the format, how the source material is considered at the time of its adaption as well as by the new creators. Novel to film adaptions often divide opinion as to whether they honour (rather than alter or sensationalise) the original text, storyline and characters. In examining the adaptations of Heart of Darkness we can consider how the story evolves from the passive reading of the postcolonial narratives through to the active participation in morally ambiguous decisions and virtual war crimes. The paper will consider how the stories blend historical fact with the original fiction for different mediums and platforms, and reflect on how these morphs or distort the original story. That Heart of Darkness has been adapted for video games is unsurprising. The signature elements of Conrad's writing: faraway settings; dramatic conflicts between human characters and the brutal forces of nature; themes of individualism; violent side of human nature and prejudice; all make for an intriguing game world. The story further suits the medium of video games as developers can demonstrate modern interpretations of Conrad’s psychopolitical situations and draw parallels between the inner lives of single characters and the broader sweep of human history. Like the original Heart of Darkness, the games utilise real places and real events to deliver stories around the same themes. Whether that is order from chaos, good versus evil, hypocrisy of imperialism, transformation or descent into madness. What the games provide in contrast to other mediums and indeed for many other games is that they both focus on hostile game mechanics and emphasise disempowerment systems over more traditional empowerment and reward-based arrangements. The paper will conclude with a consideration of why despite critical success these games have not led to more adaptations of other stories and whether interactivity has impacted upon the feeling of immersion with a story.