This essay is a contribution to literary history that explores Edgar Allan Poe’s criticism of the transcendentalist movement and its key figure Ralph Waldo Emerson through an analysis of the short stories “The Fall of the House of Usher” and “Never Bet the Devil Your Head.” By using genre criticism to define aspects of the Gothic genre, Poe’s criticism through Gothic tropes is studied together with an intertextual reading of the short stories and historical literary objects such as letters, magazines and literary reviews that details his views on transcendentalism. The purpose of this is to see if Poe used his fictional work to criticize his contemporaries. The analysis finds that “Never Bet the Devil Your Head” includes satirical comments on transcendentalist beliefs, as well one instance of specific criticism that targets Ralph Waldo Emerson as a writer - all of which can be connected to Poe’s non-fictional correspondence with fellow literati. In “The Fall of the House of Usher” Poe utilizes aspects of the Gothic genre that function as opposites to common transcendental beliefs.