This work invites us to view the Pyrrhonist tradition as involving all those who share a commitment to the activity of Pyrrhonizing and develops fresh, provocative readings of Sextus, Montaigne, and Hume as radical Pyrrhonizing skeptics: From the aspirationalism of Sextan Pyrrhonism, to Montaigne’s skeptical fideism and his unusual approach to the writing process, to the vexing interpretive issues surrounding Hume’s skepticism, each figure offers us new insights into what it can mean to Pyrrhonize.