Abstract With its roots in psychological writings of the twentieth century, the subject of the uncanny provides ways of critically analyzing why some objects appear eerie or make us feel uncomfortable. For researchers building on this appraisal, the uncanny is now associated with realistic, human-like characters featured in film and video games. Such characters may fall into an “Uncanny Valley” as their increased realism evokes a negative affective response in the viewer. This chapter presents a possible psychological explanation of the uncanny in virtual characters, based on a perception of a lack of empathy in a character. Aspects such as a lack of facial mimicry and a belief that there is an inability to forge an attachment with a character may lead to an abnegation of self and evoke the uncanny. An assessment is also made of how old and new definitions of the virtual may be applicable or untenable to the uncanny.