This course offers an investigation of the uncertain grounds opened between representation, existence and the world. Our discussion will concentrate on the relations between representation and subjectivity probing how articulation in and through its formal aspects enables us to engage meaningfully with the world, with ourselves and with other subjects. From early modernity to the present we find a self-divided condition unhinging, failing, and making uncertain the relations between fabricated representation and the world. This failure opens a relentless gap, between the production of representation and its perception, which constitutes the modern subject struggling to make sense of her own experience. While this struggle stems from the rational revolution, it may also keep dogmatism at bay. Under these conditions the practice of art may be considered as the ongoing activity of casting doubt, such that produces failures in order to illuminate fabricated truths and expose the condition of their production. Untying the logical rule of the ego cogito while producing concepts and images that do not adhere to a logocentric order is the work of the doubting artist always syncopated, excluded, failed, excessive. We will focus on the uncertain activities of failing and erring facilitating a retreat from orthodox order while promoting embracement, laughter, and non-sense through perception, language, judgment and knowledge.