[8] Chandrashekhar was the leading man in films like Surang (1953), Kavi and Mastana (both 1954), Baradari (1955), Kali Topi Lal Rumal (1959), Street Singer, and in a negative role in Basant Bahar.

From 1971 onwards until 1987, he acted as a character actor in films like Hum Tum Aur Woh, Dharma, Gehri Chaal, Charitraheen, Vardaan, Ranga Khush, Shakti, Shankar Dada, Anpadh, Saajan Bina Suhagan, Karmayogi, The Burning Train, Namak Halaal, Nikaah, Ayaash, Maan Gaye Ustaad, Disco Dancer, Sharaabi, Sansar and Hukumat.

Chandrashekhar decided to work as an assistant director to Gulzar at the age of 50, when he felt, he needed to do more in the film industry.

He also played the character role of Arya Sumant as Dasharatha's prime minister in Ramanand Sagar's TV series Ramayana at the age of 65.

In late 1988, Chandrashekhar was offered roles as "old man" in-character roles of policemen, fathers or judges in films like Tamacha (1988), Elaan-E-Jung, Mera Pati Sirf Mera Hai, Jawani Zindabad, Gurudev, Humshakal (1992) and Waqt Ka Badshah.