Kajol left her school St. Josephs convent at Panchgani and started her career at the age of seventeen. Her debut film was 1992's Bekhudi, which was a box office failure. In 1993, she shot to fame with her second film, Abbas-Mustan's thriller Baazigar. The film saw her co-starring alongside Shahrukh Khan, with whom she later went on to make a popular pairing in a number of films, all of which were box office successes. Kajol had only one release in 1996, Bambai Ka Babu, opposite Saif Ali Khan, which was a box office failure. In 1997, Kajol starred in Gupt: The Hidden Truth. Co-starring actors Bobby Deol and Manisha Koirala, the film was one of the highest grossing films of that year. Apart from that, her performance was a significant development for female actors in Bollywood; she was the first female actor to win the Filmfare Award for Best Performance in a Negative Role. Her next film release that year was Hameshaa. Like Karan Arjun, the film dealt with reincarnation, but unlike the latter, it failed at the box office. She next starred in her first Tamil film, Minsaara Kanavu. The film won Kajol her only Best Actress award at the Southern Filmfare Awards ceremony. Her final release of that year was the romantic-comedy Ishq, where she was paired with her then-future husband Ajay Devgan. It performed well at the box office. Kajol had further success in 1998, as she was the main lead starred in three of the year's biggest hits. She first starred opposite Salman Khan in the comedy Pyaar Kiya To Darna Kya. The film was the fourth highest grossing film of the year. Her next release, Dushman alongside Sanjay Dutt, did moderately well at the box office. She had a double role in the film, and won her first Star Screen Award for Best Actress for her performance. She next starred opposite Ajay Devgan in the romance Pyaar To Hona Hi Tha, which was the second biggest hit of that year. However, her biggest success that year came with her final release, Karan Johar's directorial debut, Kuch Kuch Hota Hai, which paired her again with Shahrukh Khan and went on to become the biggest hit of the year in both India and overseas. She played the role of Anjali, a young college student who is secretly in love with her closest friend, and many years after breaking contact meets him again after the death of his wife. She won her second Filmfare Best Actress Award for her performance.Kajol's first release in 1999 was the drama film Dil Kya Kare. She played the supporting role of Nandita Rai, which was well received. She had a hit with her second release, the family drama Hum Aapke Dil Mein Rehte Hain. Starring alongside Anil Kapoor, Kajol received another Best Actress nomination at the Filmfare.
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In 2005, she appeared on the TV show Kaun Banega Crorepati hosted by Amitabh Bachchan. She was paired with her husband Ajay Devgan. They won 1 crore (10 million) rupees and donated this to a cancer hospital in Chennai. She has also appeared on Indian Idol, seasons one and two, as a guest judge. She appeared on Karan Johar's talk show Koffee with Karan with Shahrukh Khan on the first episode. She also appeared on the last episode of the Season 1 together with Shahrukh Khan and Amitabh Bachchan. Back again with Season 2 of Koffee with Karan, Karan's first episode started with Kuch Kuch Hota Hai reunion. After almost a decade since his directorial debut Karan invited her along with Shahrukh and Rani Mukerji. She modeled and walked the ramp for Manish Malhotra's fashion display Fashion Week 2006, titled Freedom, along with actress Preity Zinta. In 2006, 4 miniature dolls under the name Bollywood legends were introduced. Besides Priyanka Chopra, Hrithik Roshan and Shahrukh Khan, she is one of the dolls. In 2008 she, her husband Ajay Devgan and her mother Tanuja were jury members in the TV show Rock'n'Roll Family. She appeared with Shahrukh Khan in the special anniversary issue of the Indian Vogue in October 2009. Apart from being goodwill ambassador and patron of the Britain-based Loomba Trust - a charity devoted to educating widows' children, particularly in India, Kajol also works with an NGO called Shiksha. She is a recipient of the Karamveer Puraskar award (26 November 2008), which recognises individuals who have been pivotal in leading change beyond their business by being committed to social issues.