This article is devoted to the vocal works of the outstanding Russian composer Alexander Vladimirovich Tchaikovsky. The perspective of the study is the manifestation of theatricality in the composer’s vocal cycles. The quality of theatricality was formed by the conditions of Tchaikovsky’s personal formation in the atmosphere of professional activity of the closest members of his family. His father, Vladimir Alexandrovich Tchaikovsky, was the director of the Stanislavski and Nemirovich-Danchenko Moscow Music Theatre. His work in the 1960–70s had a huge impact on the personality of the future composer. His uncle, Boris Alexandrovich Tchaikovsky, was an outstanding Soviet composer. The vocal cycles of Alexander Tchaikovsky show the tendency towards theatricalisation of vocal works, which developed in Western European and Russian musical art of the 19th and 20th centuries.