Ideas related to virtuality, simulation, fake images and copies abound in discussions of computationally generated images. Moreover, these ideas are frequently associated with the emergence of computers and seen within a broader historical arc of technological developments from photography, film and television. Such ideas are framed as having material consequences (such as those related to the production and distribution of images) and ontological consequences (such as the impact of such ideas on identity, meaning and truth). What is frequently missing from these debates is the understanding that the ontological dimension relates to a distinct and detailed history of spiritual and philosophical discourse, spanning many centuries and cultures. This chapter discusses philosophical ideas around likenesses, and how they inform debates about meaning and images in the digital age. Seeing the world as an image is part of many longstanding metaphysical ideas about meaning and reality, and this chapter considers how these ideas inform contemporary discussions about computational culture and virtuality. The method for reflecting on these themes partly derives from the third century philosopher Plotinus’ ideas on contemplation: a philosophical journey of self-discovery in which inner reflection mirrors or relates to the world, and a picture of how human nature is essentially part of the very essence of what it is to be a likeness or image. The chapter also considers how art and imagination play a central role in technological development and of the creative interactions of artists with technology. The contemplative philosophy found in Plotinus and other spiritually minded philosophies across many cultures and traditions points to ways to engage with technology in new ways and to redefine questions about real and virtual worlds. The chapter’s originality lies in the way it brings to bear key ideas from philosophy and spirituality upon contemporary discourses in computational culture.