Edgar Allan Poe is an author whose contributions to American Literature are great. He is known for his creative short stories and poems, but also for the invention of crime fiction. His unique style of writing stems from Gothic fiction, which is known for its dark and symbolic setting, horror atmosphere, mysterious characters and events as well as evoking fear. Furthermore, the peculiarity of his work is seen through his fascination and desire to explore the secrets of human psyche, especially madness as the dark and macabre side of human mind. Thus, he expressed this fascination through his short stories. Some of his most famous and eerie stories that deal with madness, and which are analyzed in this paper, are undoubtedly “The Black Cat,” “The Tell-Tale Heart,” and “The Fall of the House of Usher.” They evoke feelings of horror within the readers through portraying the narrations of individuals whose ill mind has control over them and thus makes them do the most repulsive deeds possible. The detailed portrayal of madness and its manifestation through the narrators’ behavior, the horror, the suspense, and the first person narrator is what makes these stories so terrifying, yet so stirring. Consequently, this paper will offer the portrayal of some of Poe’s most prominent features of writing, the analysis of the stories in terms of madness and horror, and, lastly, the comparison of the stories.