In 2006, Kapoor played opposite Kareena Kapoor in two films—the thriller 36 China Town and the comedy Chup Chup Ke.[25] 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. The former was his first commercial success since Ishq Vishk.[26] Greater success came to Kapoor later that year when he starred alongside Amrita Rao in Sooraj Barjatya's romantic drama Vivah, a film depicting an arranged marriage. Made on a shoestring budget of ₹100 million (US$1.5 million), the film earned over ₹530 million (US$7.9 million) worldwide, and proved to be Kapoor's highest-grossing film to that point.[27][28] Reviews of the film, however, were negative; Raja Sen termed the film a "nightmare" and wrote that Kapoor "isn't offensively bad, doesn't ham it up like crazy, or speak in a weird accent. Having said that, he isn't an actor at all, standing around working on his boyish grin, simply chewing up the scenery. No screen presence at all."[29]
Kapoor found no success in his first release of 2007—the ensemble comedy Fool & Final.[30] However, his second release that year, the Imtiaz Ali-directed romantic comedy Jab We Met proved to be one of the top-grossing films of the year.[30] The film tells the story of a troubled businessman (Kapoor) whose life undergoes a series of changes after he encounters a loquacious girl (Kareena Kapoor) on a train ride. Ali thought that Kapoor's previous roles failed to justify his acting potential, and thus approached him to portray a more complex character.[31] The BBC noted on how "endearing" he was in the film and Rajeev Masand of CNN-IBN wrote that he left an "indelible impression with a performance that is understated and mature" in a film he thought primarily belonged to Kareena Kapoor.[32][33] For his performance, Kapoor received his first nomination for the Filmfare Award for Best Actor.[16]
After featuring opposite Vidya Balan in the romantic comedy Kismat Konnection (2008), Kapoor played twin brothers, one with a lisp and the other with a stutter, in Vishal Bhardwaj's critically acclaimed caper thriller Kaminey (2009).[34][35] In preparation, Kapoor met speech specialists and researched on the medical and mental aspects of the two conditions.[36] To create a lean physique for one of the brothers, a look he considered to be "radically different" from his personal appearance, Kapoor practiced functional training and followed a rigorous diet.[36][37] Writing for Variety, critic Joe Leydon reviewed that Kapoor "impressively displays sufficiently variegated degrees of emotional intensity to sustain the illusion of two distinct characters. Just as important, he provides each sibling an appropriately elevated hunkiness quotient."[38] Rediff.com listed Kapoor's performance as the best by a Bollywood actor in 2009 and he received a second Best Actor nomination at Filmfare.[16][39] Kaminey earned over ₹700 million (US$10 million) worldwide.[28] Kapoor's final release of 2009 was as a cricketer in Dil Bole Hadippa!, a romantic comedy co-starring Rani Mukerji. It was screened at the Toronto International Film Festival, but was a financial failure.[40][41]
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