This paper examines the relationships between Romantic painting, poetry, and philosophy, historically tracing the circulation of images used to communicate sublimity (for example, images of ruins, storms, volcanoes, and so on). Kant's "Critique of Judgment" deployed the same vocabulary of images that appear in Coleridge and Shelly, in Church and in Turner. The discussion thereby places Kant's 3rd Critique within its cultural context. But it also reveals the massive shift from Enlightenment rationalism to 19th century historicism that Romanticism enacted, and Kant's resistance to, and unwilling participation, in that shift. For the nostalgic logic of ruins, and the irruption of geological time, both of which were conceived and negotiated through sublimity, cannot be assimilated within Kant's philosophy. The treatment of the sublime in the "Critique of Judgment" represents Kant's philosophy straining at its own limits in the attempt to develop a philosophy of history and to articulate an historicized philosophical anthropology. Therefore, read through art history, Kant's 3rd. Critique represents a vital transition between Enlightenment rationalism/beauty and Romantic historicism/sublimity, along with the work of Beethoven, Goya, and the Marquis de Sade.