This essay aims to investigate how Thomas Pynchon’s The Crying of lot 49, when juxtaposed with Edgar Allan Poe’s Dupin short stories, can be read as a parodic reworking on the genre of detective fiction. By placing the works of the two authors in relation to theoretical lines of detective fiction, the essay intends to highlight how the world-views of the two authors are distinctively formed, especially in terms of a hermeneutical search for ultimate meaning.