The aim of the present work is to study the crisis of a society in transition with particular references to Tennessee Williams and Anton Chekhov. This has a particular reference to Williams' A Street car Named Desire and Chekhov's The Cherry Orchard. These plays have strong resemblances as both of them portray almost identical problems. As it is, transition is a state of tensions. A sense of insecurity, uncertainty and anxiety clouds the people's minds as people of the outgoing generation are in a difficult situation. Their compulsion to part with the past and their inability to make adjustments with the present form the core of this.