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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".
Prakash Jha's big-budget ensemble political drama Raajneeti was Kapoor's first release of 2010.
The film was his first commercial success, in which his role was that of a womaniser who is romantically involved with three women, played by Bipasha Basu, Minissha Lamba, and Deepika Padukone, at different stages of his life. In Dharma Productions's Wake Up Sid, a coming of age film from director Ayan Mukerji, Kapoor portrayed Siddharth "Sid" Mehra, a rich, lazy teenager whose life undergoes a series of changes after interacting with an ambitious journalist (played by Konkana Sen Sharma).
When Mukerji narrated the then-untitled script of the film to him, Kapoor came up with the title himself.
He was cast as Kabir "Bunny" Thapar, a commitment-phobic photographer, a character Kapoor found to be an extension of himself.
After a year-long absence from the screen, Kapoor featured as a mysterious thief in Roy (2015), a romantic thriller which critic Sarita Tanwar described as a "boring, exhausting and pretentious" film.