Initial success and setback Sengupta started his career with a teleserial, titled
Mahaprabhu, which aired on
Doordarshan. He earned critical acclaim for portraying the younger
Chaitanya Mahaprabhu in the series. After his part ended in the series, he made his
silver screen debut through
Priyojon, directed by Dinen Sengupta, which was a critical and commercial failure. In 2002, he played
Thakur in Sukanta Roy's ambitious venture
Chelebela alongside
Debashree Roy playing
Kadambari Devi. Thereafter, he appeared in a string of critically and commercially unsuccessful ventures, as main lead. He made his debut in
Bangla cinema through
Moner Majhe Tumi, appearing as a parallel lead, which was the highest-grossing film of
Bangladesh in 2003. He went on playing supporting roles in commercial films, namely
Abhimanyu,
Kurukshetra,
Mahaguru,
Sangram,
Sajani,
Guru,
Janmadata,
Chore Chore Mastuto Bhai and
Premi, earning a low degree of success. In 2008, he starred in the romantic-comedy film
Love and
Bor Asbe Ekhuni. He also made his debut in
Bollywood through
Shyam Benegal's
biographical war film Netaji Subhas Chandra Bose: The Forgotten Hero.
Collaborations with Rituparno Ghose and success After appearing in critically and commercially unsuccessful films, he met director
Rituparno Ghosh, which made Sengupta put more thought into his choice of films. Under Ghosh's tutelage, he gave some of his critically acclaimed performances in films, including
The Last Lear,
Shob Choritro Kalponik (2008),
Chitrangada, and a betrayed husband in
Abohoman.
Shob Choritro Kalponik also won the
National Film Award for Best Feature Film in Bengali in 2009.
The Times of India stated that "Jisshu Sengupta, in the role of a junkie, has delivered one of the finest performances of his career." (in
Chitrangada: The Crowning Wish). Sengupta portrayed the
protagonist in
Noukadubi, alongside
Raima Sen,
Riya Sen and
Prosenjit Chatterjee in an extended guest appearance.
Comeback to Hindi cinema and recent work Sengupta made a comeback to Hindi cinema through a cameo appearance in
Anurag Basu's directorial
Barfi!. Sengupta collaborated with
Srijit Mukherji for the latter's
musical drama film Jaatishwar co-starring
Prosenjit Chatterjee and
Swastika Mukherjee. Released on 17 January 2014, the film opened to widespread positive reviews from the critics and was commercially successful. Sengupta played a supporting character in
Mardaani, starring
Rani Mukherji. In 2015, he portrayed
Byomkesh Bakshi in
Anjan Dutt's directorial
Byomkesh Bakshi. He next collaborated with
Srijit Mukherji for the latter's drama film
Rajkahini. Both of the films opened to widespread commercial success upon release. His other release in 2015, the musical drama film
Arshinagar flopped, though his performance earned critical acclaim. In 2016, he starred in the
sequel of Byomkesh Bakshi and
Zulfiqar, the former being a commercially and critically successful venture, whereas the latter was only a commercially successful venture, though his performance was critically acclaimed. He was honoured with the Best Actor award for the film
Abar Aranye in the 12th Kalakar Awards in 2004 for . He then went on to feature in the film
Manikarnika: The Queen of Jhansi (2019), where he played the role of
Gangadhar Rao, the king of Jhansi, alongside
Kangana Ranaut. The film was a commercial success. He next featured in
Shakuntala Devi, where he played the role of Paritosh Banerji,
Shakuntala Devi's husband, with
Vidya Balan playing the titular role. The film streamed on
Amazon Prime Video in July 2020. He was then offered a role in
Mahesh Bhatt's
Sadak 2, where he played the role of
Alia Bhatt's father, released in August 2020 in
Disney+ Hotstar. Sengupta played ACP Abhay Singh in the horror thriller
Durgamati, released in December 2020. In 2025, Sengupta made his comeback to
Bangladeshi cinema after nearly 23 years with
Borbaad, co-starring
Shakib Khan; having previously appeared in the 2002 film
Moner Majhe Tumi. ==Other works==