This chapter looks at how anthropomorphism works with an extremely “alien” species, i.e., the octopus. After reviewing some recent literature about octopuses and the issues that are raised about their intelligence and consciousness, the chapter analyzes the 2020 documentary My Octopus Teacher and the 2022 novel The Mountain in the Sea by Ray Nayler, showing how this form of “alien” intelligence has captured contemporary imagination. However, it is finally argued that, despite the enormous differences separating octopuses from humans, the fact of their vivid intelligence pushes us to try and bridge the great gap separating us from them—an effort that we are not ready to make for other species much more similar to us, like, for example, bats.