The skepticism of Michel de Montaigne is often conceived of as a precedent to René Descartes’ experiments in hyperbolic doubt, contributing to the emergence of rationalism in seventeenth-century France. This study proposes a different reading of Montaigne’s thought and legacy, and a fundamentally different intellectual relationship between Montaigne and Cartesian thought. It asserts that Montaigne’s Essais did not promote or practice a hyperbolic or rationalist skepticism in which no empirical knowledge can be constructed, but a form of skeptical empiricism in which both sense perception and the reasoning mind serve as tools which remain highly fallible, yet serve as a means of constructing provisional hypotheses to form knowledge. This skeptical empiricism is opposed to the totalizing doubt of Descartes, and his method of forming fully certain a priori rationalist principles as a consequence of his rationalist skepticism. In addition, this study traces the history of the skeptical empiricism of Montaigne and its influence over French seventeenth-century philosophy and philosophical fiction, asserting that contrary to serving as an antecedent to Descartes, Montaigne’s skeptical empiricist thought gave rise to an intellectual tradition which would fundamentally oppose Cartesian rationalism throughout the seventeenth century. These skeptical empiricists, from Charron to the anti-Cartesian satirist Gabriel Daniel, combat Cartesianism by reserving philosophical inquiry to the mind’s interactions with sensory phenomena and asserting the impossibility of understanding the essences of God, the mind, and things in the world. Like Montaigne, they also pose critiques of rationalist philosophical method—in which a priori principles are contemplated without reference to prior philosophical traditions—by promoting and practicing maximally eclectic interactions with other philosophies in order to produce new provisional theories about the nature of reality and improve judgement by exercising it on various philosophical texts and views.