After the demise of his father, Sudipto Chatterjee was taken under the wings of theatre acting legend Ajitesh Bandopadhyay, who went on to become his friend, philosopher and guide. His association with theatre started with watching the productions of Ajitesh Bandopdhyay. He recounts how Ajitesh was fired
from ‘Nandikar’ and went on to form his own group ‘Nandimukh’. The masterextracted a promise from his disciple that he would not get involved with any theatre performances before graduation. After Ajitesh Bandopadhyay died, Sudipto Chatterjee joined ‘Chenamukh’ helmed by Ramaprasad Banik. He was the first
person to stage a play written by Sudipto Chatterjee. He also gave Sudipto his first shot at theatre acting.