After graduating from the Institute of Stage Arts in 1926, he began acting in the Young Spectator's Theatre in Leningrad.

Cherkasov debuted in film with the supporting part of hairdresser Charles in Vladimir Gardin’s Pushkin biopic The Poet and the Tsar (1927).

He also played Jacques Paganel in the memorable 1936 adaptation of Jules Verne's The Children of Captain Grant.

In the 1947 comedy Springtime Cherkasov appeared alongside other icons of Stalinist cinema, Lyubov Orlova and Faina Ranevskaya.

He died in Leningrad in 1966 and was buried in Tikhvin Cemetery, the "Necropolis of the Masters of Art", at the Alexander Nevsky Lavra.