Chaim Zhitlowsky was born in 1865, in the small town of Ushachy, in the province of Vitebsk Governorate, Russian Empire. When he was five years old, his parents moved to Vitebsk, the capital of the province. On his mother's side he was descended from artisans and merchants, on his father's—from an aristocratic and well-educated family. His father, Joseph, studied to be a rabbi in the Yeshiva of Volozhin, but chose to become a merchant. Though an ardent Lubavich Chassid he was well versed in Haskalah (enlightenment) literature, and often recited satiric Haskalah tales and poems in Yiddish and Hebrew at family gatherings.