At the age of 6 years he played in the Prithvi Theatre his father Prithviraj Kapoor, where he played until 1957. A little later he also took roles in films directed by his older brother Raj Kapoor ( Awaara, 1951). After 1957 he toured with a British theater group and acted in Shakespeare's plays in English. He met his future wife, who died in 1984 from cancer actress Jennifer Kendal, know.
In the 1960s, Shashi Kapoor turned back to the film work and was, until the 1980s, a busy performer. In 1961 he had his breakthrough with Yash Chopra Dharmputra and the following year he played under the successful director Bimal Roy in Prem Patra. After he had shared film appearances with almost all stars of the Bollywood film industry of his time.
In the U.S. Hermann Hesse Siddhartha film adaptation (1972 ), he played the title role. 1975 Shashi Kapoor won for his supporting role in Deewaar the Filmfare Award for Best Supporting Actor. Convincing was his appearance in Shyam Benegals Junoon (1979). In 1982, he played a lead role in James Ivory's Heat and Dust India epic based on the novel by Ruth Prawer Jhabvala. For New Delhi Times him a National Film Award was presented in 1986 as Best Actor. As aging Urdu poet he took effect in 1993 in custody for the second time in a film by Ismail Merchant on, in 1963 played Kapoor in his film Householder.
His only directorial effort is the Indo- Soviet production Ajooba (1991). He appeared in over 150 films. In 1978 he founded the Prithvi Theatre, which his father had closed 18 years ago, in memory of this again in Bombay.
Shashi Kapoor belongs to the Kapoor acting dynasty, which also includes his brother Shammi and his nephew Ranbir alongside his father and his older brother Raj and his granddaughters Karisma and Kareena Kapoor.