After passing out of college, Anil Chatterjee started to work as an assistant director along with his relative, Ardhendu Mukherjee - a successful producer-director of the period. Later, Ardhendu Mukherjee directed one of Anil Chatterjee's major films as a hero - Bandhan (1962) - opposite Sandhya Roy. Although Anil Chatterjee aimed at being a successful film director, he made several small appearances in films made by his friends. Anil Chatterjee first assured his audiences with a character role in Ritwik Ghatak's Nagarik (1952). His first significant role was in Jog Biyog (1953) directed by Pinaki Mukherjee, a close friend. Dhuli (1954) was another film, directed by Pinaki Mukherjee that featured him. Ulka (1957), directed by Naresh Mitra brought Anil Chatterjee much acclaim in the role of its idealistic hero Sudhir.
After Nagarik, Anil Chatterjee went forth doing an important role in Ghatak's second film Ajantrik (1958), which did not have much commercial success. His next film with Ritwik Ghatak was Meghe Dhaka Tara (1960). In this film, Anil Chatterjee offered a spellbinding performance as Shankar, the elder brother of the film's protagonist Neeta - Supriya Devi. Anil Chatterjee had a rare capability of in capturing the shades of the character selfishly single-minded in his pursuit for excellence. He also had another great performance opposite Supriya Devi in Ghatak's Komal Gandhar (1961), as the theatre worker Rishi.
Anil Chatterjee's career with Satyajit Ray began with the film Devi (1960), featuring Sharmila Tagore; where he had a small role. In the Post-Master story of Teen Kanya (1961) - 3 woman-centric short stories by Rabindranath Tagore made for the screen by Ray - Anil played the character of Nandalal, a music lover who comes to a remote village with the job of the post-master. He has worked in other films of Satyajit Ray too, including Kanchanjungha (1962), Mahanagar (1963) and others. Anil Chatterjee was felicitated at the Berlin Film Festival (1964) and also at the Acapulco Film Festival, M‚xico in 1963.
Anil Chatterjee was also a favorite artist of director Tapan Sinha. He played significant roles especially in Sinha's early films, including Louhakapat 1957), Nirjan Saikate (1963) and Jotugriha (1964). Anil Chatterjee was excellent in each of the roles. The famous film Sagina Mahato (1970) featured Anil Chatterjee in the memorable role of Aniruddha, sharing the screen with the legendary Dilip Kumar. In the final phase of Anil Chatterjee 's career he did character roles in Sinha's Atanka (1986) and Aaj Ka Robinhood (1987).
Anil Chatterjee's reputation as an actor mainly depended on his performances in films by Satyajit Ray, Ritwik Ghatak and Tapan Sinha. However, he was also seen in brilliant performances in many artistically competent popular films. One such film was the Marutirtha Hinglaj (1959) by Bikash Roy. The film was an epic film about a group of pilgrims on a laborious venture to the holy Hinglaj temple in Baluchistan. In the same year he was again seen as a patient in a mental asylum in Asit Sen's smash-hit Deep Jweley Jai (1959). In Ahobaan (1961) Anil Chatterjee was cast as a romantic hero opposite Sandhya Roy and the film proved to be one of the biggest hits of the year.
Film Ek Din Achanak Anil Chatterjee also acted in films like Sandhya Dweeper Sikha (1964), Pinaki Mukherjee's thriller Faraar (1965), Notun Jibon (1966), Panchashar (1968), Khunjey Berai (1971), Bon Palashir Padabali (1973), Chhanda Patan (1974) and Amanush (1974). He acted with the legend Uttam Kumar in several films. Eventually, he settled down with offbeat films like Utpalendu Chakraborty's National Award winner Chokh (1983), Aparna Sen's Paroma (1984) and Gautam Ghose's Paar (1984). Anil Chatterjee also did justice to his characters in Amol Palekar's Hindi film Ankahee (1985). He also gave a memorable performance in a television serial - Naqab, directed by Palekar. He acted for the first time in Mrinal Sen's film Ek Din Achanak (1989).
In 1953, he got married and had three sons and one daughter. He was a strong believer in Marxist ideals and thus held the post of the President of Federation of Film Technicians & Workers of Eastern India and Shilpi Sansad, Kolkata. He has also been a Member of the Govt. of India's Cine Workers Welfare Fund and served as a member of the Governing Body of Nandan, the art-film theatre complex established by the Govt. of West Bengal. Anil Chatterjee was also was the Vice-President of the West Bengal branch of the Indo-Soviet Friendship Society. In 1991, he made history by becoming the first non-Congress candidate to represent Kolkata's Chowringhee Assembly constituency in the West Bengal Vidhan Sabha.
With his death on 17th March 1996, Bengali cinema lost one of its best actors and one of its most loved and respected human beings. The name of Anil Chatterjee is still remembered as an enigmatic persona in the Indian film industry.
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