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Kapoor was attracted to the idea of playing an unlikable lead since it was a departure from the traditional portrayal of teenage heroes in Indian films.Writing for The Hindu, the critic Ziya Us Salam did not find him to be "hero material", adding that "boyhood seems to have overstayed on his face – but he is not necessarily bad in the acting department." The thriller Fida (2004) featured him as a love-struck student who is manipulated by a woman (Kareena Kapoor) and her lover (Fardeen Khan) to rob a bank.Just as important, he provides each sibling an appropriately elevated hunkiness quotient." Kapoor's final release of 2009 was as a cricketer in Dil Bole Hadippa! It was screened at the Toronto International Film Festival, but was a financial failure.In 2010, Kapoor reteamed with Ken Ghosh in Chance Pe Dance, a comedy-drama about a struggling actor, in which Kapoor's performance was described as "uneven" by Aniruddha Guha of Daily News and Analysis.Kapoor's highest-grossing releases came with the period drama Padmaavat (2018) and the romantic drama Kabir Singh (2019).In addition to acting, Kapoor supports charities, hosts award ceremonies, and has featured as a talent judge on the dance reality show Jhalak Dikhhla Jaa Reloaded (2015).Kapoor appeared as a background dancer in a few films of the 1990s, and was later featured in music videos and television commercials.He made his film debut in 2003 with a leading role in the romantic comedy Ishq Vishk, a sleeper hit for which he won a Filmfare Award for Best Male Debut.

In 36 China Town, a murder mystery from the director duo Abbas–Mustan, Kapoor starred as one of the seven suspects in the murder of an heiress, and in the Priyadarshan-directed Chup Chup Ke, he played a depressed man who pretends to be deaf and mute.

Kapoor, who trained extensively for a bulkier physical build, was eventually hired.

Ishq Vishk tells the story of Rajiv Mathur (Kapoor), a high-school student who engages in a romantic affair with two classmates of contrasting personalities (played by Amrita Rao and Shenaz Treasurywala).

He followed it with roles in several commercial failures before starring in Sooraj Barjatya's top-grossing family drama Vivah (2006).

Kapoor earned nominations for the Filmfare Award for Best Actor for portraying a troubled businessman in Imtiaz Ali's romantic comedy Jab We Met (2007) and twin brothers in Vishal Bhardwaj's thriller Kaminey (2009).

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