Recently, cognitive scientists like Clark (2016) and Hohwy (2013), alongside computational neuroscientist Karl Friston (2006, 2013) have conceptualized the mind as a hierarchical prediction system, at levels varying from the “merely” sensory to the highly conceptual. Here, we extend this thesis in order to understand the hermeneutic process as it relates to textual and artistic encounters. We argue that one of the foundational mechanisms of the artwork, as it is contemporarily conceived, can be meaningfully conceptualized as a cognitively rich interaction which, by design, informs and exploits the mind’s predictive system. We further show how this mechanism, and a predictive framework more generally, help explain a host of traditional literary, aesthetic, and art historical values, including ambiguity, defamiliarization, and reversal.