After a career on stage in Leningrad, Cherkassov began playing small comic roles in films, such as Vladimir Gardin's Poet i tsar / The Poet and the Tsar (1927). His first major dramatic roles were the leading part in Iosif Kheifits's and Natan Zarkhi's Deputat Baltiki / Baltic Deputy, and that of the tsarevich Alexei in Vladimir Petrov's Pëtr I / Peter the Great (both 1937). He has played Gorky, Pavlov, Rimsky-Korsakov and Mayakovsky, but shot to international prominence with his title roles in Sergei Eisenstein's Aleksandr Nevskii / Alexander Nevsky (1938) and Ivan Groznyi / Ivan the Terrible (1944-45, Part Two released 1958). Cherkassov accompanied Eisenstein when he was summoned to see Stalin, Molotov and Zhdanov in 1946 to discuss the "errors" of Part Two of the latter film. After Stalin's death, Cherkassov made his last major film appearance in Grigori Kozintsev's Don Quixote (1957). He was also a deputy to the USSR Supreme Soviet.