AI is not only a technology but also a powerful story about the latent future present. This narrative assemblage is visible across domains of industry, policy, academia, and debate. Characteristically, it bifurcates into binaries of possibility versus risk, augmentation versus replacement, and so on. This calls for a renewed critique. In this chapter, we argue for the importance of bothering these binaries by re-thinking AI as anticipatory existential media that allows for the unexpected, the impredicative, and the uncanny. Three voices from the continental tradition of philosophy offer possibilities for pluralizing the AI imaginary. Jaspers’ existentiality brings the reality of the vulnerabilities of the present digital limit situation to the fore, requiring response; Derrida’s hauntings allow the past to return as friendly and wise ghosts; and Bloch’s hopefulness challenges the inevitability of the processes at hand. Together, they allow us to reimagine more unruly AI futures in fruitful and urgent ways.