Abstract: The paper presents a comparative analysis between George Bernard Shaw and Anton Chekhov, two key figures who exerted a great influence on dramatic realism. Dramatic realism is a theatrical movement that originated in the mid-19th century and was a reaction against the sensationalism of Romanticism and melodrama, to catch the thereness of everyday life, with sincerity. It drew on realistic dialogue as well as ordinary characters and dwelt on interpersonal conflicts as opposed to external conflicts.Although both playwrights were determined to portray reality, there were a lot of differences in their methodologies, focus areas, and theatrical impact.On the one hand, the Irish author and playwright Shaw was an advocate of didactic realism, where the idea of his so-called plays of ideas was used crassly, as a direct means of social criticism and intellectual rhetoric. He used to make his characters mouthpieces of his Fabian socialism views that challenged Victorian morality, as well as promoting reformation. Chekhov, the Russian master did in contrast to cultivating a subtle and psychologically-oriented realism. His plays were unconventional in dramatic structure as he focused on the inner world of the small people, their unfulfilled desires, ineffective communication resulting in unclear tragicomic endings. Shaw addressed social evils head-on, in order to educate and challenge the society into making a change, through intellectual debate. The way Chekhov developed his style, full of subtext and taking on the slice-of-life kind of approach, invited people to ponder on all the ambiguities and complexity of the human condition. This comparative analysis has shown that although both playwrights stimulated the genre of realistic theatre, Shaw had an overt reformist program compared to Chekhov who was discreet in his trend of theatre artism. Their individual contributions also expanded the dramatic realism of expression, having made an unforgettable contribution on modern theatrics as well as future generations of the theatrics and playwrights.