The article aims to confront the skeptical critique of cognition with Nietzsche's refutation of classical epistemology. Irrespective of some striking analogies, it does not purport that skepticism exerted direct impact on Nietzsche's philosophy. Nevertheless, both critiques reject such a type of philosophy that endeavors to discover the very nature of things and both repudiate the dogmatic dichotomy of the 'apparent' and the 'true' world that since Plato has become an integral part of nearly every metaphysical project. The ancient skeptics and Nietzsche demonstrate that every cognition is determined by various physiological, social and cultural contexts and, consequently, the Greek thinkers seem to agree with the German philosopher that concepts such as 'reality' or 'world' are but interpretations conditioned by the very structure of the human sense organs and basic human needs. In the light of the contingent and situational character of our knowledge, the skeptics and Nietzsche dethrone the discourse of science and philosophy by showing not only the genesis of our propositions but also the possibility of opposite, yet equally justified, propositions. Thus, 'world' transpires to be a necessary illusion and every attempt at explaining it is relegated to the position of just one of the manifold perspectives attainable. In the final analysis, the article offers a reevaluation of the skeptical project, as it advances a thesis that the ancient and Nietzschean skepticisms show the insurmountable limitations of every cognition, protest against any endeavor to establish an absolute account of reality and, thereby, opt for a continuous striving for new interpretations and perspectives.