V.S. Srinivasa Sastri was born on 22 September 1869 in a small village, Valangaiman, along the banks of the Kudamurutti nearly 300km south-west of Madras (now Chennai). He was fourth child born to his orthodox Brahmin parents, Vaidik Sankaranarayana Iyer Sastri and Balambal Sastri. Srinivasan was preceded by three sisters and, in due course, an equal number of brothers followed. His father had inherited the family profession of teaching and reciting Sanskrit scriptures and, by all accounts, a life of rituals and pecuniary struggle awaited the eldest son. The family was very poor, and Sankaranarayana, in spite of trekking near and far in search of a dedicated clientele, earned little.

Sankaranarayana was exceedingly strict in his observation of rituals and enforced them unfailingly in his own household. He was also emotionally volatile, which meant that fatherly warmth and dramatic outbursts were both par for the course in the household. Srinivasan's mother could not have been temperamentally any more different. Balambal was calm and composed and consequently a stabilizing influence on Srinivasan. He later recalled that his mother had ‘a melancholy and pious disposition’ and cultivated in him the trait of listening. Her ‘street expositions of scriptures’ and bountiful resources of mythological lore kept the young Srinivasan enchanted but also grimly terrified of the mystical world of goblins and ghosts. He found his solace in the outside world, playing marbles and digging street pits, and quickly distinguished himself as a marble player of local repute among the neighbourhood children.

Once he hit school-going age, Srinivasan was sent to the Native High School, six miles away in Kumbakonam, where he stayed until matriculation. On most days, ‘shirtless Srinivasan’ walked to school, too poor to afford one anna for the bullock cart and, as the nickname reveals, sometimes even without a shirt. He was an unusually bright student, however, and the founding headmaster, Rao Bahadur Appu Sastri, nurtured him. While Srinivasan received ample doses of conservative Hinduism at home, Appu Sastri awakened in him a spirit of reform and liberalism. The headmaster introduced him to the wider world through newspapers, history books and magazines, and parliamentary records, and induced in his pupil ‘an early subdual of passions’.