This paper will look at Kant’s views of the aesthetic experience, in relationship to Buddhist philosophical and political discussions of art and social organization. The primary focus in Kantian literature explores the relationship between free and dependent beauty, as well as Kant’s paradox of taste. The central argument of the Kantian portion is going to navigate the paradox of taste via Graham Priest’s epistemic and conceptual distinction pertaining to the limits of thought. Secondly, I shall contextualize the debate with similar argumentation found in medieval Tibetan literature, by thinkers such as Tsongkhapa and Drakpa Gyaltsen. Lastly, I shall look at the political and artistic state of affairs in Yuan and Ming Dynasties and assert the applicability of both Kantian and Tibetan discussions of effibility in the context of Tibetan poetry and Thangkas.