[9] Chakraborty made his acting debut with the art house drama Mrigayaa (1976), directed by Mrinal Sen, for which he won his first National Film Award for Best Actor.

[10] Chakraborty gained greater fame with the 1982 film Disco Dancer, which was a major box office success in India and the Soviet Union.

[19] In 1992, he, along with Dilip Kumar and Sunil Dutt, set up a trust to help actors in need of assistance called Cine & T.V Artistes Association (CINTAA).

[20] He was also the Chairperson of Film Studios Setting & Allied Mazdoor Union, which protects the welfare of cinema workers and resolves their demands and problems.

[31] That same year, he played a brief role in Dulal Guha's hit thriller Do Anjaane which had Amitabh Bachchan, Rekha and Prem Chopra in the lead.

[44][45] Its soundtrack composed by Bappi Lahiri was a huge chartbuster and played a big role in the box office success of the film, especially in countries like Soviet Union and China.

[49][50] The following year, he appeared alongside Shashi Kapoor, Moushmi Chatterjee and Ranjeeta in the family drama film Ghar Ek Mandir.

[52] Chakraborty gained more recognition in 1985 with Vijay Sadanah's romantic drama Pyar Jhukta Nahin, acting opposite Padmini Kolhapure.

[55] He followed it with a superhit in J. P. Dutta's action drama Ghulami co-starring Dharmendra, Naseeruddin Shah, Reena Roy, Smita Patil and Anita Raj.

[54] Chakraborty's dream run continued in 1986 with the success of K. Bapayya's family drama film Swarag Se Sunder, which also had Jeetendra, Jaya Prada and Kolhapure in the lead.

[59] Apart from commercial success, he received acclaim for his performance in Basu Chatterjee's Sheesha, which was the first Hindi film centred around sexual harassment at workplace.

[61] In 1988, Chakraborty reunited with K. Bapayya for Pyar Ka Mandir, co-starring Madhavi, Nirupa Roy, Sachin Pilgaonkar, Raj Kiran and Shoma Anand.

[63] 1989 also proved to be a big one for Chakraborty with four of his films emerging commercial successes, which were - Daata, Prem Pratigyaa, Mujrim and Aakhri Ghulam.

[64] Chakraborty began the new decade with average fares, such as Pati Patni Aur Tawaif and Humse Na Takrana, while his most notable release of 1990 was Mukul Anand's action crime film Agneepath alongside Amitabh Bachchan, which although a commercial failure, received highly positive response from critics and won him Filmfare Award for Best Supporting Actor.

[67] Chakraborty's career as a matinee idol faded in the mid-1990s as he took a break from mainstream Hindi cinema and started working in low-budget productions, most of which lacked success due to their poor quality.

[27] During this phase, he saw moderate successes in Shapath (1997) and Chandaal (1998) and won the National Film Award for Best Supporting Actor for playing Ramakrishna Paramahansa in G.V.

From 2000 to 2003, he appeared in highly acclaimed films like Nepaldev Bhattacharjee's Chaka (2000), Rituparno Ghosh's Titli (2002), Prasanta Bal's Ferari Fauj (2002) and Narayan Rao's Santrash (2003).

[86][87] Chakraborty's performance of an honest editor met with immense acclaim and he received a nomination in the Filmfare Award for Best Supporting Actor category.

[100] That same year, he appeared in Vibhu Puri's critically acclaimed historical drama Hawaizaada alongside Ayushmann Khurrana and Pallavi Sharda.

[103] It received negative reviews from critics, but the audience reception was positive and as a result, it ran in cinemas for more than 100 days, eventually emerging as a sleeper hit at the box office.

[107] Despite receiving polarizing response from reviewers, it grossed ₹3.40 billion (US$39 million) worldwide and was declared a major blockbuster by the end of its run.

[108][109] He received another nomination in the Filmfare Award for Best Supporting Actor category for his performance of a retired IAS officer in The Kashmir Files.

[121][122][123] He appeared as a co-judge with Karan Johar and Parineeti Chopra on the reality show Hunarbaaz: Desh Ki Shaan, which premiered on Colors TV in January 2022.

[125][126][127][128][129] Chakraborty joined as a Member of Parliament[130] after he was nominated for the Rajya Sabha Member of Parliament elections by the Chief Minister of West Bengal Mamata Banerjee for her All India Trinamool Congress (TMC) in the West Bengal Rajya Sabha Assembly Polls which were held on 7 February 2014.

[132] Chakraborty joined the Bharatiya Janata Party (BJP) on 7 March 2021, ahead of the 2021 West Bengal Legislative Assembly election, in the presence of Prime Minister Narendra Modi and Kailash Vijayvargiya.