Leonid Chupyatov studied at the Drawing School of the Society for the Encouragement of Arts (1909-1910), studios of Jan Tsionglinsky and Mikhail Bernstein, the school of Elizaveta Zvantseva in St. Petersburg-Petrograd (1909-1918), and the Petrograd State Free Art Workshops (1918-1919) under Kuzma Petrov-Vodkin. He lived in St. Petersburg and painted portraits, landscapes, and still lifes.

Chupyatov participated in exhibitions since 1916 and was a member of various art associations. He also worked as an animator on the creation of the animated film "The Tale of the Silly Little Mouse" (1940) based on the poem by Samuil Marshak. Chupyatov taught at various educational institutions in Novgorod, Kiev, and Leningrad from 1919 to 1933. He died of starvation during the blockade of Leningrad. His works are in several museum collections, including the State Russian Museum.