[2] Dymov was born in Białystok, in the Grodno Governorate of the Russian Empire (present-day Poland).
Yosif attended a Russian gymnasium, and went on to study at the Imperial Forestry Institute in St. Petersburg,[3] graduating in 1902.
At the age of 16 he began to publish humorous stories in Russian satiric journals.
[3] At that time he took the pen name 'Osip Dymov', from the character in Anton Chekhov's short story "The Grasshopper" (1892),[4] and continued to write under that name throughout his career.
[2] The latter play had its premiere in 1919 in a Yiddish translation, at the Jewish Art theatre of Jacob Ben-Ami; it was later translated into English and performed at the Astor Theatre on Broadway, in 1922,[5] to mixed reviews.