Stanley Cavell and Thierry de Duve have independently proposed that judgments of the type “This is art” are aesthetic judgments, to be understood along the lines of Kant’s analysis of the judgment of taste. Contrary to the common philosophical strategy of pursuing a definition of art that could be applied to controversial cases, Cavell and de Duve reinterpret the art-judgment as a reflective aesthetic judgment that claims universal agreement on non-conceptual grounds. Accordingly, judging something to be a genuine artwork is not a preliminary step but an inherent part of our aesthetic engagement with art. Furthermore, the transcendental grounding of such judgments implies that some universal and necessary conditions of human experience are revealed in the domain of art. Yet, our analysis shows that the two positions disagree on (1) the role of distinct artistic media as being essential (Cavell) or inessential (de Duve) to the art-judgment; and (2) the relation of criticism to judgment in the experience of art. Both points are related to the philosophers’ differences regarding the material aspect of artistic experience, as well as to some further moments in their respective appropriations of Kantian aesthetics. We propose that combining the complementing insights of the two positions contributes to defining the common framework of our experience of art in its characteristic contemporary diversity. Specifically, it serves to negotiate the still much relevant tension between the high modernist position represented by Cavell and the post-conceptual position represented by de Duve.