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actress, Kapoor was embodying a maturer, more jaded character ahead of her years in Bewafaa which appeared peculiar for a young woman of her age.Later that year, she appeared in Priyadarshan's romantic drama Kyon Ki, which was set in a psychiatric hospital, and relates the love story of a mentally ill patient, played by Salman Khan, and his physician, played by Kapoor. The film was a box office failure,though Kapoor's performance was generally enjoyed by critics, with the BBC reporting, "It goes without saying that she is a pure natural when it comes to acting.Kapoor then was cast in the romance Dosti: Friends Forever. While not a success in India, the film became the highest-grossing Bollywood film of 2005 in the United Kingdom.
Shortly afterwards, she was cast for the first time as a villain in the thriller Fida. The film follows the story of an on-line robbery and the Mumbai underworld with which her character Neha Mehra becomes involved. During the filming of Fida, Kapoor entered into a relationship with actor Shahid Kapoor, whom she later described as having "a major positive influence in my life. Although the film did not succeed at the box office, Kapoor garnered positive reviews for her performance, with some critics noting a distinct progression from her earlier roles. Her subsequent releases that year included Abbas-Mustan's moderately successful thriller Aitraaz and Priyadarshan's comedy Hulchul, her first box office success since 2002.
Following the negative period in Kapoor's career, 2004 marked the beginning of her work in more serious films, most of which would bring her critical acclaim rather than commercial success. Under the direction of Sudhir Mishra, Kapoor portrayed the role of a prostitute in Chameli. The film relates the story of a young prostitute who meets with a widowed investment banker (played by Rahul Bose), and follows the development of their relationship as they share their devastating life experiences. When Kapoor was initially offered the role in 2002, she refused it, stating that she was reluctant to play a bold role at the beginning of her career.However, when the director again approached her a year later, she agreed to do the film and viewed it as an opportunity to show the range of her acting skills. To prepare for the role, she visited several of Mumbai's red-light district areas at night to study the dress and mannerisms of sex workers. Chameli received predominantly positive reviews upon release and Kapoor's performance was generally well-received by critics, with the Indiatimes praising her "intuitive brilliance" and stating that she had exceeded all expectations. Another reviewer, however expressed concern that they found her portrayal unconvincing and excessively stereotypical, describing her as "sounding more like a teenager playacting than a brash, hardened streetwalker", and likening her mannerisms to that of a caricature. Nonetheless, Kapoor's portrayal of Chameli garnered her the Filmfare Special Performance Award and the film marked a significant turning point in her career as an actress.
She next co-starred in Mani Ratnam's bilingual project Yuva alongside Ajay Devgn, Abhishek Bachchan, Vivek Oberoi, Rani Mukerji and Esha Deol. The film, consisting of three chapters, tells the story of six individuals linked by a car accident. Kapoor is featured in the third chapter as Oberoi's love interest, Mira, a young witty woman. She was mostly criticised for taking a role of minimal importance, though her performance was generally well-received.Subhash K Jha described her role as "fey and insubstantial", but further stated that "she turns these character traits to her own advantage to create a girl who is at once enigmatic and all-there, a bit like the film itself which is both mysterious and voluptuous She then appeared alongside Amitabh Bachchan and Fardeen Khan in Govind Nihalani's critically acclaimed film Dev, which revolved around the 2002 Hindu-Muslim riots in the Indian state of Gujarat. Kapoor's role was that of a Muslim victim named Aaliya, modelled after Zaheera Sheikh, a key witness in Vadodara's Best Bakery case. It earned her a Filmfare Critics Award for Best Performance, as well as nominations for Best Actress at various award ceremonies. Taran Adarsh commented, "Kareena Kapoor is first-rate. Sporting a deglamorized look, the actress takes a giant leap with this film. Her scene with Amitabh Bachchan (when the latter asks for witnesses to come forward) is an example of superb acting.
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