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In the wake of Douglas Crimp's passing in July 2019, Johanna Burton reflects on her still-evolving intellectual and personal relationship with this figure so crucial to histories of art, activism, and critical writing. Briefly tracing the various areas of thinking with which Crimp was associated over his decades-long career, Burton argues that the sum of Crimp's trajectory of thought is much greater than any of its formidable parts. Crimp has perhaps been most often associated with the onset of a particular tenet of postmodernism, namely the formation of the “Pictures Generation,” (including artists like Troy Brauntuch, Jack Goldstein, Louise Lawler, Sherrie Levine, Robert Longo, and Cindy Sherman). Yet Crimp, dissatisfied with the limits of this discourse, moved in the early 80s purposefully away from it toward other evolving dialogues: first around the AIDS crisis, and later into film, dance, memoir, and beyond. Ultimately, Crimp's legacy, Burton argues, is defined by his desire to unseat rather than produce or maintain established thinking. He models theoretical paradigms that anticipate their own eventual irrelevance in order to make space for others.