Shahid Kapoor was born in New Delhi on 25 February 1981 to actor Pankaj Kapur and actor-dancer Neelima Azeem. His parents divorced when he was three years old; his father shifted to Mumbai (and married the actress Supriya Pathak) and Kapoor continued living in Delhi with his mother and maternal grandparents. His grandparents were journalists for the Russian magazine Sputnik, and Kapoor was particularly fond of his grandfather: "He would walk me to school every single day. He would talk to me about dad, with whom he shared a great relationship, and read out his letters to me."

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. He had a supporting role in Paathshaala, a drama about the education system in India, starring Nana Patekar, following which he starred in Yash Raj Films' Badmaash Company, a comedy-drama about a group of overambitious youngsters who become con men. Rachel Saltz of The New York Times praised Kapoor's look in the film, though Tushar Joshi of Mid Day thought that he was miscast. Kapoor's fourth and final release that year was Satish Kaushik's romantic comedy Milenge Milenge, which marked his fourth collaboration with Kareena Kapoor. Plagiarised from the Hollywood film Serendipity, the production was delayed since 2005. During its production in December 2004 at Phuket, Kapoor requested a delay in filming to attend the premiere of Dil Maange More. The delay may have saved the lives of the crew, since the hotel booked for them was destroyed during the 2004 Indian Ocean tsunami. With the exception of Badmaash Company, none of these films performed well commercially. Kapoor next appeared in his father's directorial Mausam (2011); co-starring Sonam Kapoor, the star-crossed romance set over a decade, took two years to complete. Considering the film to be his "dream project", Kapoor did not take on additional work while filming for it. For his role as an unambitious village boy who becomes an air force pilot, Kapoor trained to fly the F-16 Fighting Falcon. Rajeev Masand reviewed that "while he doesn't quite cut it as a convincing IAF pilot, Shahid Kapoor is terrific as the small-town brat". The film was a box office flop and Kapoor was later regretful for spending so much time on the project. The following year, Kapoor took on another romantic role in Kunal Kohli's Teri Meri Kahaani (2012), co-starring Priyanka Chopra. It tells the story of a pair of star-crossed lovers who are reincarnated in three different eras. Filmfare reviewed that "Shahid and Priyanka give it their best shot, but their charm doesn't make up for the absence of a genuine kahani [story]". The comedy Phata Poster Nikhla Hero from director Rajkumar Santoshi was Kapoor's first release of 2013. His role was that of Vishwas Rao, a struggling actor who masquerades as a policeman. Critical reviews on the film were negative, though Kapoor's performance was praised. As with his last few releases, the film earned little at the box office leading trade analysts to question his commercial appeal. This changed later that year, when he starred in Prabhu Deva's action film R... Rajkumar; despite a negative critical reception, the film earned over Rs995 million (US$15 million) worldwide, becoming Kapoor's highest-grossing release to that point. In a scathing review, Saibal Chatterjee of NDTV called the film a "massive mess" and wrote that Kapoor "ends up looking more moronic than macho" in it. Kapoor suffered from burn injuries on his back and hands while filming a stunt sequence in R... Rajkumar. CANNOTANSWER

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In 2010, Kapoor reteamed with Ken Ghosh in Chance Pe Dance,