This study is a unique correction of a misperception regarding works by two of nineteenth century America’s literary giants: Edgar Allan Poe (1809-1849) and Mark Twain (1835-1910). By examining their lives within the social, political, and technological climates of their respective times, the author presents a strong argument for his new and radical reading of Poe’s Narrative of Arthur Gordon Pym and Twain’s The Great Dark (1898) as being America’s literary counterparts to Rousseau’s social theories. Arguing against the prevailing sentiment that Poe’s novel is merely popular fiction and that Twain’s tale is an unfinished diatribe, this study clearly delineates their serious attempts to reverse the moral malaise of nineteenth century America through personal spiritual renewal via the aegis of dream transcendence.