The Christian Orthodox icon, with its ambiance of spiritual piety, reverence and meditation, is also a channel for the uncanny – the sensation of unease, mystery, secrecy and ambiguity as discussed by Freud in his seminal 1919 essay. Examining the aesthetic and theological aspects of an icon reveals further unique associations with the uncanny (in its various guises) and plays a complex, crucial role in the engagement with the icon as intended or as an unwitting conduit of the uncanny. The icon and the uncanny are bound even closer when considering the work of contemporary artists who nod to Orthodox traditions in an unorthodox fashion. The result is artwork that evokes the uncanny. Yet sensing the uncanny drives the spectator to question and assess the motivation and meaning of the images shown, in a bid to rid oneself of the uncanny associations the work evokes.