In 2008, she co-starred alongside Akshay Kumar, Saif Ali Khan and Anil Kapoor in Vijay Krishna Acharya's action-thriller Tashan. Though a poll conducted by Bollywood Hungama named it as the most anticipated release of the year,[60] the film eventually became a commercial and critical failure.[61][62] She next provided her voice for the character of Laila, the love interest of a street dog named Romeo, in the Yash Raj Films and Walt Disney Pictures animated film Roadside Romeo. It was the second Bollywood film to receive a North American release by a Hollywood studio.[63] In preparation for the role, Kapoor viewed several Hollywood animated films to analyse how actors delivered their dialogues.[64] Kapoor then appeared in Rohit Shetty's comedy Golmaal Returns, the sequel to the 2006 film Golmaal. A part of an ensemble cast that included Ajay Devgn, Arshad Warsi and Tusshar Kapoor, Kapoor played a distrustful wife who believed her husband to be unfaithful. The film received ambivalent reception from critics and Kapoor herself received mixed reviews. The Indian Express believed the screenplay was unoriginal, concluding, "There is nothing particularly new about a suspicious wife keeping tabs on her husband, and there is nothing particularly new in the way Kareena plays it."[65] Golmaal Returns was nonetheless a major financial success, with revenues of Indian rupee793 million (US$ 18 million) internationally.[32]In 2009, Kapoor was cast as Simrita Rai opposite Akshay Kumar in Sabbir Khan's battle of the sexes comedy Kambakkht Ishq. Set in Los Angeles, California, it became the first Indian film in history to be shot within Universal Studios Hollywood, California, and featured several cameo appearances from Hollywood actors.[66] The film earned over Indian rupee840 million (US$ 19.07 million) worldwide, but was a critical failure.[32] The Times of India described her performance as "a complete let-down" and further stated that "despite her haute-coutured look, her micro minis, her pencil heels, she comes across as a completely unconvincing supermodel cum surgeon."[67] She next starred in Prem Soni's directorial debut, Main Aurr Mrs Khanna. Kapoor featured as the protagonist, Raina Khanna, a woman who becomes the sole breadwinner of the family, and therefore struggles with her marriage. The film was critically and financially unsuccessful,[68] with the Daily News and Analysis concluding that "Kapoor shows moments of the talent we associate with her, but then slumps with a silly drunken scene or by just smiling beatifically through emotional moments."[69]Following Main Aurr Mrs Khanna, Kapoor's next release was Kurbaan, a dramatic thriller set against the backdrop of global terrorism.[70] It was directed by Rensil D'Silva and written by Karan Johar, co-starring Saif Ali Khan, Vivek Oberoi, Om Puri and Kirron Kher. Kapoor played the role of Avantika Ahuja, a woman who is confined to house arrest after finding out that her husband is a terrorist. She described the film as "an emotionally draining experience", which did not let her disconnect from her character during shooting.[70] Upon release, the film was critically embraced and Kapoor received her fourth Filmfare Best Actress nomination.[4] According to Subhash K Jha, "Kurbaan belongs to Kareena Kapoor. In her most consistently-pitched performance to date she pulls out all stops to play a betrayed wife with splendid sensitivity. Kareena accommodates her radiant beauty into an utterly credible character and performance. At her best, Kareena is incomparable. She proves it in 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.[8] 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.[36] 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.[36] 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.[36] 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.[37] 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.[38] Nonetheless, Kapoor's portrayal of Chameli garnered her the Filmfare Special Performance Award[4] 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 generallywell-received.[39] 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".[40] 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.[41] Kapoor's role was that of a Muslim victim named Aaliya, modelled after Zaheera Sheikh, a key witness in Vadodara's Best Bakery case.[41] It earned her a Filmfare Critics Award for Best Performance, as well as nominations for Best Actress at various award ceremonies.[4] 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."[42Shortly 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."[43] Although the film did not succeed at the box office,[44] Kapoor garnered positive reviews for her performance, with some critics noting a distinct progression from her earlier roles.[45] 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.[44]
In 2005, she starred as the protagonist in Bewafaa, a drama directed by Dharmesh Darshan. The feature received mostly negative reviews and Kapoor's portrayal of Anjali Sahai, an unfaithful woman, was not well-received.[46] Nikhat Kazmi of Indiatimes believed that in an effort to become a serious 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.[46] 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,[47] 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."[48] 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.[49]"Kareena is an apt Desdemona to Ajay Devgn's Othello. As young Dolly who elopes with a man she is madly in love with and ultimately becomes a victim of his violent jealousy, Kareena is brilliant. Her vulnerability is palpable, her expression of love endearing [...] Kareena internalises her character with stupefying intelligence and throws up a performance that leaves you overwhelmed. And she makes it look so effortless."
—Filmfare on Kapoor's performance in Omkara (2006)[50]In 2006, Kapoor appeared in three films. She first starred in the thriller 36 China Town followed by the comedy Chup Chup Ke; both films performed reasonably well.[51] She next portrayed the Shakespearean character of Desdemona in Omkara, the Hindi adaptation of William Shakespeare's Othello. Directed by Vishal Bhardwaj, the film is a tragedy of sexual jealousy set against the backdrop of the political system in Uttar Pradesh.[52] The film premiered at the 2006 Cannes Film Festival and was also selected for screening at the Cairo International Film Festival.[52][53] Omkara was embraced by critics and Kapoor's portrayal earned her a fourth Filmfare Award and first Star Screen Award;[4] her performance was later included in the 2010 issue of the "Top 80 Iconic Performances" by Filmfare.[50] Kapoor herself considers her role in Omkara as a "new benchmark" in her career and has made comparisons between her portrayal of Dolly and her own evolving maturity as a woman.[54Following Omkara, she stopped acting for a short time, as she felt that "nothing [was] challenging enough for me to say yes".[54] In an interview with The Times of India, Kapoor commented, "In my initial years in the industry, I pushed myself to do a lot of work because I was greedy. I did some films – which I now regret – purely for the money. Today, I want to do selective films."[55] She later described this period as a way to "relax and unwind" herself.[56]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.[8] 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.[36] 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.[36] 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.[36] 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.[37] 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.[38] Nonetheless, Kapoor's portrayal of Chameli garnered her the Filmfare Special Performance Award[4] and the film marked a significant turning point in her career as an actress.[8][11]
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.[39] 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".[40] 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.[41] Kapoor's role was that of a Muslim victim named Aaliya, modelled after Zaheera Sheikh, a key witness in Vadodara's Best Bakery case.[41] It earned her a Filmfare Critics Award for Best Performance, as well as nominations for Best Actress at various award ceremonies.[4] 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."[42]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,[44] Kapoor garnered positive reviews for her performance, with some critics noting a distinct progression from her earlier roles.[45] 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.
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