Anton Chekhov was one of the most illustrious and celebrated short-story writers in the history of literature. Trained as a physician, he pursued his career of a medical practitioner without giving up on his passion for writing which he discovered when he was young. Interestingly, writing happened incidentally to Chekhov who started off by writing humorous letters to his family in Moscow, while he was in Taganrog to uplift their morale as the family faced trying times. Following this, he started writing materials which soon were featured in newspaper periodicals and literary journals. Initially writing for monetary gains, his artistic ambitions later forced him to concentrate on quality work as he came up with the evolution of what is today known as modern short story. His most impressive works as a short story writer and playwright include, ‘The Cherry orchard’, ‘The Seagull’, ‘Uncle Vanya’, ‘Three Sisters’ and ‘Lady with the Dog’.