Philosophy and Everyday Life is the first monograph in English on the thought of Thompson Clarke (1928–2012). The essay has both (a) exegetical and (b) systematic ambitions. (a) It provides the first close reading in the literature of Clarke’s seminal paper “The Legacy of Skepticism,” the brilliance of which is matched by its near-impenetrable density. I defend an interpretation of “Legacy” that puts Clarke at odds with perhaps his greatest admirer, Barry Stroud, whose work can be read as a multifaceted exploration of ideas and problems inspired by Clarke. Reading “Legacy” through the lens of Stroud suggests what I call ‘the Dissolutionist Reading,’ which views Clarke as attempting to ‘dissolve’ the skeptical challenge. Against that, I propose what I call ‘the Pyrrhonian Reading,’ which develops Myles Burnyeat’s suggestion that Michael Frede’s interpretation of Pyrrhonism is ‘Clarkean.’ On the Pyrrhonian Reading, Clarke’s reflections on skepticism end not with dissolution, but with suspension of judgment. (b) I contend, further, that traditional epistemology still has a great deal to learn from both Clarke and Pyrrhonism. On the Pyrrhonian Reading, Clarke is best understood as arguing that the legacy of (modern, Cartesian) skepticism is (ancient, Pyrrhonian) skepticism. This reorientation involves divorcing global skeptical problematics from the dogmatic assumptions of Cartesianism, locating them instead in the ancient conceptual framework that I refer to as ‘the metaphysical appearance–reality distinction.’