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Scholars interested in the moral significance of art in Kant’s account of aesthetic ideas in the Critique of Judgment (CJ) tend to focus on art’s ability to represent what Kant calls “moral ideas.” They further suggest that, in representing these ideas, art symbolizes our capacity to act according to moral laws. I argue that this reading fails to adequately capture the complexity of Kant’s account, for art’s capacity to represent moral ideas is intrinsically related to its ability to prompt a specific kind of mental operation among the audience—that is, a harmonious cooperation of imagination and understanding. Through this mental operation, the audience creatively interprets the ideas that the artwork expresses. I then discuss how this harmonious cooperation between the two mental faculties can develop our moral imagination—a capacity necessary for the performance of what Kant calls “imperfect duties.” While poetry is Kant’s highest-valued art form in terms of its ability to express aesthetic ideas in the CJ, his anthropological writings show that tragedies, comedies, and novels can also stimulate and cultivate our imaginative capacities. I therefore argue that Kant’s account of these narrative genres gives us a more comprehensive understanding of how representational art can shape our mental faculties.