This dissertation argues for a melancholic reading of Montaigne’s Essais, through the lens of early-modern notions of melancholy and folly, placing Montaigne “in a motley” and “in tears,” and hence, fully within his period. As such, Montaigne is seen to embody one of the most complex, unique, and critical forms of subjectivity: early-modern melancholic subjectivity, as it will be surveyed in this dissertation through a wide variety of literary and visual concepts and figures that engage and resonate with one other, to produce the “world” of early-modern melancholy, rather than just a psychological state. A reading of Montaigne’s Essais as a melancholic text will demonstrate the consistency and unity of a text famous for its heterogeneity and diversity. If these diverse parts of the Essais, ranging from cats to fathers, from honesty to cruelty, from the act of essaying to the critique of custom, from Montaigne’s views on passions to his views on death, can all be read and enveloped within [one] melancholy, then the implications are both that melancholy is not a pathology defined by lack, but rather a subjectivity, and moreover — a privileged subjectivity, whose insight and critical abilities now parallel those of the “privileged” work of the Essais, as a work of immense complexity, singularity, value, and meaning.