Is it still possible in the post-structuralist era to talk about a distinct essence of literature? This chapter radically reassesses the theoretical implications of the collapse of structural essentialism for the ontology of literature and art, treats the widespread equation between literature and literary language as merely a reductionist structuralist assumption and argues that the essential distinctness of literature/art should still be treated as an open question. It goes on to trace the implications of this theoretical assumption for linguistic pessimism: the reasons behind the literary individual’s discontent with language go far beyond the pervasiveness of the phenomenal in human experience, and are rather linked to the nature of literature as a distinct output of human cognition. Questions about the essential distinctness of literature, on the one hand, and the literary individual’s discontent with language, on the other, seem to stand in an interesting feedback relationship: if literature had a distinct essence, this might help explain why linguistic pessimism is more intensely experienced by the literary mentality, while at the same time the fact that linguistic pessimism is more widespread among literary individuals provides some ground for exploring anew the possibility that literature is an essentially distinct object.