This article examines the contradiction in Kant’s writings concerning genius as both continuous and discontinuous with imitation, focusing primarily on whether genius imitates. While originality without any imitation is inconceivable and impossible, an original artwork is not imitative, as imitation is servile and entirely opposed to genius’s freedom. Some scholars have attempted to resolve this contradiction by selectively reconstructing Kant’s concepts of imitation, while others have reduced his thought to one side of it. Focusing on Kant’s evaluation of his own examples of genius (Milton, Shakespeare, and Michelangelo) and non-genius (Klopstock) in his lectures and handwritten notes, this essay proposes that his thinking about imitation and genius remains irresolvably contradictory. It also reflects on how this impasse shapes Kant’s conception of (in)imitability, deformity, tradition, and convention in art.