This dissertation proposes that the oeuvre of Rimbaud is the next major link in the line of radical Pyrrhonian writing launched by Montaigne’s Les essais. Although some have noted that Rimbaud read Les essais and was excited by a passage concerning poetic inspiration, this dissertation proposes a different model of intertextuality showing that both writers created a Pyrrhonian structure of poetics and poiesis (concerning the inspiration for and creation of texts) as a response to a crisis. This model contends that Montaigne helps uncover an ongoing Pyrrhonian crisis through his popularization of ancient skepticism in his “Apologie de Raymond Sebond.” This crisis, which includes the paradox of radical doubt (that we can doubt our very act of doubting too), entails the suspension of judgment, but it also requires trying out different ideas and beliefs. Montaigne thus created a new form of writing about a mutable and multiple way of thinking and being in response to the crisis. Rather than taking a philosophical approach, this dissertation argues that Montaigne also turned to the power of poetry (and its need for ambiguity, vanity, and imagination) to find new and truer ways of reading and writing the world and the self. Rimbaud also wrote about a similar crisis, such as in his short story “Un cœur sous une soutane” which shows a young seminarian poet in his own personal and poetic crises. His Une saison en enfer expresses a metaphysical crisis, where the narrator-poet searches for a new way of believing and being, and a poetic crisis, where he both turns against his former poetic program, and presents the poems of his past, a dual structure of (non-)palinody recalling the (non-)apology structure of Montaigne’s “Apologie.” His texts continue to oscillate between new ideas and ways out of the crises and moments of despair and doubt, and through this oscillation, Rimbaud creates a new form of Pyrrhonian writing. This unique take on Montaigne and Rimbaud has implications for the radical practice of poiesis and poetics as responses to an unresolvable but generative Pyrrhonian crisis.