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In this chapter, I discuss the possibility of a “productive” imagination as it plays out in the context of postmodern philosophy, and the philosophy of Deleuze and Guattari in particular. Despite the promising suggestion that imagination can be productive in Deleuze’s early work, in Anti-Oedipus, Deleuze and Guattari consistently bemoan the merely “imaginary” consequences of desire understood as lack, which implies that they still take the imagination to be a merely representational faculty. I then challenge this claim by turning to Deleuze and Guattari’s critique of representation and treatment of art as a “monument” from What is Philosophy, and Deleuze’s account of cliché in Francis Bacon: The Logic of Sensation. As I demonstrate, once we abandon the representational image of thought, as Deleuze consistently urges us to do, then the imagination itself can be meaningfully rehabilitated as a productive capacity to clear away stale images and allow for genuine creativity and novelty.