In 2008, he played the negative role of Mohan Kanta, a British Indian army man who betrays his revolting pro-independence military regiment in the horror film 1920, written and directed by Vikram Bhatt. He was to act in the movie Dus but the project got shelved. In 2004, he starred in the film Shukriya: Till Death Do Us Apart which also starred Aftab Shivdasani, Shriya Saran and Anupam Kher. He also appeared in a television show on STAR Plus, Pyaar ke do naam.Ek Radha Ek Shyaam. Later, he transitioned into music videos, including those for Falguni Pathak's "Pal pal tere yaad sataye" and Jagjit Singh one for the south Indian singer Yesudas's Hindi album and a remix of the old film song "Koi diya jale kahin (rum pum bum)", sung by Asha Bhosle from the movie Bees Saal Baad. He also appeared in commercials for the Tata Indigo Marina car, VIP Frenchie and Aquafina. He modelled for designer Rohit Bal and worked for choreographers Marc Robinson and Achala Sachdev. Sengupta was a finalist of the 1999 Gladrags Manhunt Contest in which John Abraham was the winner.
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