Literature has always been central to philosophical reflection on imagination, but much of that reflection has led to misguided understandings of both terms. In the Introduction to this volume, Chiara Bottici and Benoît Challand help clarify some of these problems in their outline of the two broad lines of investigation of imagination, one through the subjective legacy of Kant and another through the lens of social contexts or imaginaries. My chapter will work through both lines of investigation in order to develop a problematic that makes available literature’s relevance to political debate.