In Memoirs of Carwin the Biloquist, Charles Brockden Brown explores foundational aesthetic complexes that inform his fitful attempts to express the emergent contours of an American poetics and politics of self-fashioning. Through the youthful figure of Carwin, Brown depicts how the nascent American artist’s suffocating and repressed relationship with his patrimonial heritage provides the impetus for discovering and internalizing revolutionary, transformative, and subversive powers inherent in nature’s hidden forms. Carwin’s gradual, covert self-empowerment achieves expression not only through the agency of natural, local, and American forces but also through an allusive matrix connecting John Milton’s A Mask Presented at Ludlow Castle (1634) with William Shakespeare’s The Tempest. Brown portrays Carwin’s halting, and ultimately ineffectual, attempts to transform a poetics of imposture into a politics of subversion.