After making her acting debut in the 1992 romance Bekhudi, Kajol had her first commercial success with the 1993 thriller Baazigar.
She rose to prominence by featuring as the female lead in several top-grossing romances, including Yeh Dillagi (1994), Ishq (1997), Pyaar Kiya To Darna Kya (1998), Pyaar To Hona Hi Tha (1998) and Hum Aapke Dil Mein Rehte Hain (1999)—and received critical recognition for playing against type in the 1997 mystery film Gupt: The Hidden Truth, that earned her a Filmfare Award for Best Villain, and the 1998 psychological thriller Dushman.
However, Kajol received praise for her performance and won the BFJA Award for Best Actress.
She subsequently starred in and earned public recognition with Yash Raj Films's hit romantic drama Yeh Dillagi, alongside Akshay Kumar and Saif Ali Khan.
The film, which was an unofficial remake of the Hollywood film Sabrina, narrated the story of a chauffeur's daughter who becomes a model, and engages in a love triangle between two brothers.
In 1995, Kajol starred in two major commercial successes—Rakesh Roshan's Karan Arjun and Aditya Chopra's Dilwale Dulhania Le Jayenge—both opposite Shah Rukh Khan.
Her portrayal of a conservative NRI in the romance Dilwale Dulhania Le Jayenge (1995), a tomboy in the romance Kuch Kuch Hota Hai (1998), a loquacious woman in the melodrama Kabhi Khushi Kabhie Gham...
(2001), a blind Kashmiri woman in the romantic thriller Fanaa (2006) and a single mother in the drama My Name Is Khan (2010) garnered her five Filmfare Awards for Best Actress.
In 2011, the Government of India awarded her with the Padma Shri, the fourth highest civilian honour of the country.
Not to mention the on-screen chemistry that has become the stuff of legend." In an interview with The Hindu, director Rajiv 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".
In 1994, Kajol featured in the melodrama Udhaar Ki Zindagi, as the granddaughter of the characters played by Jeetendra and Moushumi Chatterjee.
The film, which was a remake of the hit Telugu film, Seetharamaiah Gari Manavaralu, failed to do well at the box office.