This article reappraises the relevance of Theodor W. Adorno’s aesthetics in the aftermath of the postmodern debate. It proposes a shift of focus from the concept of “semblance character” to the concept of “enigmatic character” in order to grasp what Adorno means by the “truth content” of artworks. This theoretical move is meant to shed new light on how Adorno sees the relationship between art and politics. The inclusion of Adorno in the tradition of the beautiful and his portrayal as a forerunner of Jean-François Lyotard’s aesthetics of the sublime are flawed. In other words, artworks would be true not because of what they make apparent or acknowledge as unpresentable but because their enigmatic complexion unleashes a crisis of comprehension that challenges our understanding of the world. A “maybe” emblematizes the enigma, whose imaginative appropriation remains truer to emancipation than any utopia or dystopia could ever become.