Both for Kant and for Nietzsche, aesthetics must not be considered as a systematic science based merely on logical premises but rather as a set of intuitively attained artistic ideas that constitute or reconstitute the sensible perceptions and supersensible representations into a new whole. Kantian and Nietzschean aesthetics are both aiming to see beyond the forms of objects to provide explanations for the nobility and sublimity of human art and life. We can safely say that Kant and Nietzsche used the dualities of the beautiful/sublime and Apollonian/Dionysian to advocate their general philosophical worldview, and that the initial formation (in Observations and The Birth of Tragedy) and final dissolution (in the Critique of Judgment and Zarathustra and other later works) of these dualities are determined by the gradually established telos of their philosophical endeavor. Therefore, by observing the evolution of these so-called dualities, Kaplama gathers important clues as to how Kant’s and Nietzsche’s aesthetics transformed into different ways to affirm human art and life. On the one hand, Kaplama argues, the Dionysian came to be the heart and soul of Nietzschean aesthetics and ethics, and the Apollonian (or the formal drive of individuation) was reduced into a mere aesthetic criterion. On the other, Kant treats the sublime (which is originally an idea-producing feeling and/or judgment) as a mere appendix to his Critique of Judgment and aesthetic theory teleologically reducing it into its possible moral consequences. This is why Schopenhauer calls the sublime “by far the most excellent thing in the Critique of Judgment” which touches on the real problem of aesthetics very closely but does not provide a real solution for it. Kant’s forced teleological move is to make his theory of aesthetic judgment stand as a ‘reaffirmation’ of the earlier ethical justification he believed to have accomplished in the first two Critiques and the Groundwork where he defends an affirmation of human life through a teleological morality centered on the principle of free-will. In contrast, Nietzsche’s aesthetics (particularly the Dionysian) guides his ethics and metaphysics again through defining an ideal human nature without which ethos would be static and meaningless, lacking the ability to move and change and represent the tragic pathos of human life.