Expressionism in literature was a revolutionary movement against realism and naturalism. As a twentieth century movement, it is the subject of the inner world. Like most artistic movements, it is applied to lots of art forms including Paintings, Architecture, Cinema, and Music. Dramatists like Elmer Rice and Eugene O'Neill introduced Expressionism to American Literature. This paper is a comparative study of O'Neill's The Hairy Ape and Emperor Jones based on expressionism viewpoint. Its aim is to find the expressionistic features and to compare the similarities and differences between these two works. The features and principles of expressionism in drama include: structure (for example, one-act play), main focus on protagonist and his inner conflicts, tragic ending, unnamed minor characters, employing music and light (as two prominent features of expressionism), applying symbols and colors, monologue and soliloquy or telegraphic dialogue, etc. In this paper, these were features of analysis. The research revealed the fact that there are similarities and differences between the two pieces of drama in question. Although the two plays, Emperor Jones and The Hairy Ape written by one author (Eugene O'Neill) and in one period of his life (1920-1921), and both are known as expressionist works, still there are some differences in applying expressionistic features. The similarities and differences are discussed followed by some suggestion for further research.