Using meaningful historical material, the article explores the parallels of the creative careers of such great developers of the Russian opera of the late 19th – early 20th centuries as F. Chaliapin, S. Mamontov, and V. Telyakovsky. It was the period of rapid development of innovative stage direction, vocal art, and stage design. The outstanding organizers of theater business S. Mamontov and V. Telyakovsky were at the heart of that creative seething. Being representatives of different social strata (the merchant class and higher nobility), they attracted vivid talents and opened them the way of the private and state opera, respectively. The flourishing of operatic art led to a completely new level of performance. F. Chaliapin and a number of other outstanding representatives of Russian opera began their careers at that time. S. Mamontov’s Private Opera which played a significant role in the development of Russian operatic art was founded in 1896. The repertoire of this theater consisted of works by Rimsky-Korsakov, Mussorgsky, and Borodin. Innovative approaches to the opera performance which was considered as a living synthetic phenomenon integrating the concepts of production and stage design were implemented on the Russian stage for the first time. In its productions, Mamontov’s Private Opera used the principles of realism, which corresponded to the spirit of the works performed. Meanwhile, the development of Russian opera during this period was taking place against the background of complex social relations which aggravated many contradictions both in the life of the society as a whole with its differentiation into metropolitan and provincial life, and in the life on the stage with its specific very mobile interpersonal communications. The article focuses on the careers of S. Mamontov, F. Chaliapin, and V. Telyakovsky. Each of them made an invaluable contribution to the development of Russian opera. From the perspective of the historical culturological approach, the article examines the complicated relationship between the prominent Russian philanthropist and theater director Savva Mamontov, the flexible administrator Vladimir Telyakovsky, and the outstanding opera singer Feodor Chaliapin, and their influence on the formation of the personality of an opera performer and on the development of operatic art in Russia as a whole. The article presents abundant documentary evidence of the peculiarities of their relationship which ultimately determined the vector in the development of the Russian opera theater.