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He subsequently assisted Sanjay Leela Bhansali on the film Black (2005) and made his acting debut with Bhansali's tragic romance Saawariya (2007), a critical and commercial failure.

When Mukerji narrated the then-untitled script of the film to him, Kapoor came up with the title himself.

He followed this with roles in a series of films that did not perform well commercially, with the exception of the romance Ae Dil Hai Mushkil (2016).

This changed in 2018 when Kapoor portrayed Sanjay Dutt in Rajkumar Hirani's biopic Sanju, one of the highest-grossing Indian films of all time, for which he won another Filmfare Award for Best Actor.

The series of financial failures continued with his next release, the Anurag Kashyap-directed crime drama Bombay Velvet, based on the historian Gyan Prakash's book Mumbai Fables, which also starred Anushka Sharma and Karan Johar.

Ritika Bhatia of Business Standard found Kapoor's part to be a departure from his previous roles, writing that he "does test the waters with methodical sincerity but his portrayal lacks depth on occasion".

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