The article is dedicated to the study of the theatrical legacy of Alexander Oskarovich Remez (1954–2001) – a Soviet and Russian playwright, who pioneered an atypical development line of the so-called "black comedy", where the game as a way of world perception and understanding becomes the dominant intratextual element. The study focuses on the analysis of the plays Happy Ending (1974) and Curse (1980), which are united by the affinity of authorial strategies (intimate setting, a small number of characters of close age categories, love conflict, motif of dueling, the atmosphere of the 19th century, etc.). The role of the game element is determined in the works at the levels of action development, characterization, chronotope, language, allusions, and reminiscences. In both plays, the characters engage in a game with each other, while the author plays not only with the characters but also with the readers/viewers. In Happy Ending, Remez introduces the intrigue with real names, age, and occupation of the "Man" and the "Woman", deliberately breaking the boundaries and conventionality of the "fourth wall". Special attention is paid to decorations and the musical-sound organization of the text. The dynamics of comedy and tragedy are noted. The analysis of Curse is a logical continuation of the previous research by the authors of this article, dedicated to Remez's plays Dramatic Poet (1975) and I... I... I... (1978) – very interesting examples of the artistic rethinking of the destinies of great Russian writers of the 19th century. The foundation of Curse lies in the attempt of a "dramatic study" (as defined by A. O. Remez) of Lermontov's biography, whose work attracted the playwright. The researchers put forward a hypothesis about the nature of the dialogue with pretexts, among which the "romantic chronicle" by O. Ya. Remez (the writer's father) and T. A. Chebotarevskaya "About Lermontov..." and "Notes" by E. A. Sushkova come to the fore.