Art if often concerned with situations like those imagined by the skeptic philosopher, where one cannot attain strong evidence to prove the relations between representation and the world. When considered in artistic production art challenges the fabrication of knowledge while setting new relations with the world and reality. Some maintain that we are bounded in “world-pictures” (Zeit des Weltbildes) as argued by Wittgenstein and Heidegger. This course will ask how we may think of modern and contemporary art through skepticism, doubt and uncertainty. The question at hand will explore how art may offer a systematic process akin to methodological skepticism to thus afford us an insight into the questions of the existence of external reality and the finite nature of objective knowledge. Allying with the skeptic, we will concentrate on the exploration of the limits of perception, problems of judgment,