Abstract: Ivanov, the play written by Chekhov in 1887, is seriously underestimated in the history of Russian drama.This play represents an important change in Chekhov’s conception of drama. Through Ivanov’s suicide, Chekhov tries to carry out a thorough liquidation of the tradition of “superfluous man” in the history of Russian literature, and to identify his relationship to liberals and Tolstoyism, so as to find the answer to the belief in life and what art is.In terms of drama thought, the play is not only Chekhov’s consciously successful imitation of Western classical drama, but also a complete farewell. This work of genius reflects Chekhov’s transformation from the traditional western classical drama to the modern drama, which makes Chekhov’s drama different from the classical drama paradigm followed by Lermontov, Gogol and Tolstoy. This study is of great value both to the study of Chekhov’s modern drama thought and the transformation of his creative techniques.This paper tries to reinterpret the significance and value of Ivanov in the history of drama from three aspects: the creation and performance of Ivanov, the end of the literary tradition of the “superfluous man”, and the interpretation of Ivanov’s death.