Asking why adaptation has been seen as more problematic to theorize than other humanities subjects, and why it has been more theoretically problematic in the humanities than in the sciences and social sciences, Theorizing Adaptation seeks to both explicate and redress “the problem of theorizing adaptation” through a metacritical history of theorizing adaptation from the late sixteenth century to the present, a metatheoretical theory of the relationship between theorization and adaptation in the humanities, and analysis of and experimentation with the rhetoric of theorizing adaptation. Adaptation was not always the bad theoretical object that it increasingly became from the late eighteenth century: in earlier centuries, adaptation was celebrated and valued as a means of aesthetic and cultural progress. Tracing the falling fortunes of adaptation under humanities theorization, the history nevertheless locates dissenting voices valorizing adaptation in every period. Adaptation studies can learn from history not only how to theorize adaptation more positively, but also to consider “the problem of theorization” for adaptation. The metatheoretical section finds that theorization and adaptation are rival, overlapping, inimical processes, each seeking to remake culture—and each other—in their images. It is not simply the case that adaptation has to adapt to theorization: rather, theorization needs to adapt to and through adaptation. The final section attends to the rhetoric of theorizing adaptation, analyzing how tiny pieces of rhetoric have constructed adaptation’s relationship to theorization, and turning to figurative rhetoric, or figuration, as a third process that can mediate between adaptation and theorization and refigure their relationship.