This literary study mainly analyzes the context of the selected classic short stories. The verbal data supporting the said claim are descriptively investigated based on feministic theory, psychoanalytical theory, and historical-biographical theory. The study is buttressed with related literature and study, and is done with discourse analysis. The study gathers the following findings: (1) Anton Chekhov‟s “The Lady with the Dog,” reveals feministic and gender issues that shape the story‟s plot, (2) Edgar Allan Poe's “The Cask of Amontillado” discloses psychoanalytical outlooks which show the genuine personality and role of the characters, and (3) Mark Twain's “The Celebrated Jumping Frog of Calaveras County” echoes the author‟s personal life. This study further uncloaks that Chekhov‟s short fiction portrays three feministic insights: the feminine, feminist, and female, Poe's masterpiece discloses psychoanalytic concepts on id, superego, and Freud's concept of projection, and Twain‟s work shows the author's presence in the text which compasses journey, downfall, moral failing, and dream. The utilized theories of literature for analysis provides a better understanding of the aforesaid tales. The studied short fictions hedge to gain more appreciation and comments of the people in the field of literary study.