This paper attempts to identify and systematize the main approaches to the theater of absurd and absurdist drama in Western and Russian literary studies. The term theater of the absurd was originally introduced by Martin Esslin. This concept has become a common denominator and refers to the dramatic work of such famous authors as Samuel Beckett, Eugène Ionesco, Harold Pinter, Arthur Adamov, and Jean Genet. Martin Esslin and his followers brought in several important features into the absurdist drama, i.e., alogism, disjointed communication, wordplay (Patrice Pavis), etc. They attempted to conceptualize the theater of the absurd as a part of a broader typological unit, e.g., Michael Bennett’s theater of parabola. Russian scholars and critics have developed a range of important concepts as well. They see absurd as a violation of basic rules of communication (Olga Revzina, Isaac Revzin). The Union of Real Art (Mikhail Yampolskiy, Dmitry Tokarev) focuses on the principle of serialized eventfulness. Others concentrate on the meta-descriptive nature of absurd (Evgenyi Kluev) and develop the concept of absurdity as a picture of the world (Olga Burenina-Petrova). Both in Western and Russian studies, the conceptualization of the theater of the absurd follows two opposite poles: absurd can be interpreted as either a linguistic phenomenon (deconstruction of communication), or as a certain way of human existence. During the 1980–2000s, post-structuralist philosophy played a major role in the re-thinking of the absurd, while the interaction of philosophical and literary approaches determined the principles of historical aesthetics. As suggested by contemporary researchers, the discourse of the absurdist drama has the following features: deconstruction of cultural codes; actualization of the archaic basis of theater; parodying literal and theatrical conventions; problematization of the semiotic linkage (sign and its referent); depiction of mosaic consciousness and unstable cosmos.