With the growing use of digital technologies in artworks there has been a considerable boom in the critical literature concerning the production, curation, appreciation, and philosophical import of those works. While digital aesthetics can encompass anything from a swipe on an iPad to a participatory, 'interactive,' experience with a Jeffrey Shaw installation, most digital media aestheticians are interested by the peculiarity of the digital media experience. Yet the digital medium is still defining its very existence as a medium, both in the fine arts and in the utilitarian technological sector, and so I believe that in order to better understand the present we must understand how it has affected the past. It is in this spirit that I will assess the rich aesthetics of Immanuel Kant's 'Critique of Judgment' using contemporary examples of 'digital fine art,' such as Jeffrey Shaw's "Place-Ruhr," Noah Wardrip-Fruin's "Screen," and Bill Viola's various film series.