According to wikipedia, In 1997, her portrayal of Isha Diwan, a psychopath killer in Rajiv Rai's Gupt: The Hidden Truth, was lauded by critics and proved to be a major turning point in her career.[30] She explained that playing Diwan was the "toughest role" of her career as it was "difficult to play a mean character".[31] In an interview with The Hindu, director Rai quoted, "[I] tapped the versatile artistry in Kajol in Gupt! [She] had a complex role and she certainly brought a rare finesse to her etching of that character in the film".[32] The thriller, which co-starred Bobby Deol and Manisha Koirala, also emerged as a major commercial success.[33] Kajol eventually became the first woman to be nominated in and win the Filmfare Award for Best Performance in a Negative Role.[34]
Kajol then starred as an aspiring nun in Rajiv Menon's Tamil film, Minsaara Kanavu opposite Arvind Swamy and Prabhu Deva. Kajol revealed that she found dancing alongside Prabhu Deva difficult and it "took me 20 retakes and 30 rehearsals" to get the steps right.[35] Her performance met with appreciation with The Indian Express reviewing, "Kajol is full of beans and fits into her character with commendable ease. Hers is perhaps one of the most expressive faces of the present."[36] The film was dubbed in Hindi as Sapnay and released in Northern India. The original Tamil version was a box-office success, but the dubbed version emerged as a commercial failure.[37] Her next release was Indra Kumar's romantic comedy Ishq alongside Aamir Khan, Juhi Chawla and Ajay Devgn, in which she played Kajal, a poor girl in love with a rich boy, played by Devgn. Upon release, the film emerged as a commercial success.[33]
In March 1998, Kajol appeared in her first hit of the year, Pyaar Kiya To Darna Kya, in which she played Muskaan Thakur, the love interest of Salman Khan. In her next release, Dushman, Kajol played the dual role of twin sisters, Sonia and Naina Saigal. The film, which revolved around Naina avenging the murder of her sister, won Kajol critical appreciation with reviewer Sukanya Verma writing, "Kajol is in superb form, both as the opinionated career-minded twin who is murdered, and as the avenger. Even she must have preferred less glycerine and more restraint."[38][39] For her performance, Kajol won her first Screen Award for Best Actress and received a Best Actress nomination at the Filmfare. She next starred opposite Ajay Devgn in the romantic comedy Pyaar To Hona Hi Tha, a remake of the Hollywood hit French Kiss as Sanjana, a clumsy woman who travels from Paris to India in search of her philandering fiancé. The film emerged as her second commercial success that year and fetched her another Best Actress nomination at the Filmfare.[40]
However, her biggest success that year was her final release, Karan Johar's directorial debut, Kuch Kuch Hota Hai. Co-starring Shahrukh Khan and her cousin Rani Mukerji, the film emerged as a blockbuster in both India and overseas with a worldwide gross of INR103.38 crore (US$16 million).[41][42] Kajol played Anjali Sharma, a tomboy, who is secretly in love with her best friend, played by Khan. A review carried by The Times of India wrote, "Kajol is almost mesmeric as Anjali, the firebrand youngster who doesn't know whether she should settle for best girl or basketball buddy. [...] Kajol with her baggy apparel, her bouncy bob cut and her boyish banter is absolutely riveting."[43] She eventually won the Best Actress award at the 44th Filmfare Awards ceremony for her performance in the film.[3]
In 1999, Kajol featured in a supporting role opposite Ajay Devgn, post their marriage, in Prakash Jha's drama Dil Kya Kare. She played Nandita Rai, the other woman in the life of Anant Kishore, played by Devgn. In an interview with Filmfare she explained, "The only reason, I agreed to play my character was because it had shades of grey. I would have probably refused the wife's role. Because I felt it had nothing for me to do."[31] Upon release, the film met with largely negative reviews. Critic Sharmila Taliculam, however, described Kajol as "the only person who gives her role a semblance of sanity".[44] Commercially too, the film failed to do well. However, her next release, the woman's film Hum Aapke Dil Mein Rehte Hain emerged as a critical and commercial success.[45] Starring alongside Anil Kapoor, Kajol received another Best Actress nomination at the Filmfare ceremony for her portrayal of Megha, the deceived wife of Kapoor's character. The film met with wide media coverage for being one of the few woman-centered films to emerge as a commercial success in India.[46]
In 2000, Kajol featured alongside her husband once again, in his home-production Raju Chacha. The children's film, with a production cost of INR30 crore (US$4.6 million) was described as the "most expensive Bollywood film ever", at the time.[47] Upon release, the film met with negative reviews and flopped at the box-office.[48] Her first release of 2001 was the comedy Kuch Khatti Kuch Meethi, where she played the double role of Tina and Sweety Khanna, twin sisters who are separated at birth. The film was a major commercial failure and fetched negative reviews from critics. Writing for Rediff.com, Savera R Someshwar criticised Kajol's decision to star in the film; termed her as a "glamorous prop" and described her performance as "uninspiring".[49]
Later that year, she played a leading role in Karan Johar's family drama Kabhi Khushi Kabhie Gham..., which was a blockbuster in India and the top-grossing Indian production of all-time in the overseas market until 2006.[50] Also featuring Amitabh Bachchan, Jaya Bachchan, Shahrukh Khan, Hrithik Roshan and Kareena Kapoor in prominent roles, Kajol played the role of Anjali Sharma, a young Punjabi woman from Delhi's Chandni Chowk area, who falls for the rich Rahul Raichand, played by Khan. Kajol, faced initial difficulties while filming for her scenes, as she was required to speak in Punjabi, a language she wasn't fluent in. However, she learnt the right pronunciation and diction with the help of producer, Yash Johar and the crew members.[51] Her comic-dramatic performance met with unanimous critical acclaim and won her several awards, including her third Filmfare Award and her second Screen Award in the Best Actress category.[3] Taran Adarsh labelled her as "first-rate" and predicted that her "Punjabi dialect will win her immense praise".[52] The Hindu wrote, "Kajol ... steals the thunder from under very high noses indeed. With her precise timing and subtle lingering expression, she is a delight all the way."[53][54]
Following the success of Kabhi Khushi Kabhie Gham..., Kajol took a sabbatical from full-time acting. In an interview with The Times of India she revealed, "I'm not quitting films, I'm just being selective. Fortunately, I'm in a position where I can pick and choose."[55] She added that the reason behind the break was to concentrate on her marriage and "start a family".[56]
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