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, she eventually dropped out of school to pursue a full-time career in film.
On not completing her education, she quoted, "I don't think I am any less well-rounded because I didn't complete school".
At the age of sixteen, she began work on Rahul Rawail's film Bekhudi, which according to her was a "big dose of luck".
She initially intended to return to school after shooting for the film during her summer vacations.
Inspired from the Hollywood film A Kiss Before Dying, the film co-starred Shah Rukh Khan, Shilpa Shetty and Siddharth Ray, and saw Kajol portray the leading role of Priya Chopra, a girl who falls in love with her sister's murderer.
The film marked the first of her many collaborations with Khan.
[She] had a complex role and she certainly brought a rare finesse to her etching of that character in the film".
Kajol's younger sister, Tanishaa Mukherjee is also an actress.
Her maternal aunt was actress Nutan and her maternal grandmother, Shobhna Samarth, and great grandmother, Rattan Bai, were both involved in Hindi cinema.
In that same year's retrospective review by Rediff, Raja Sen stated that Kajol was "wisely picked ...
to play Simran, the real-as-life actress bringing warmth and credulity to the initially prudish and reluctant Simran.