[16] As part of tradition, along with the Mukherjee family, Kajol, a practising Hindu, celebrates the Durga Puja festival in the suburban neighbourhood of Santacruz annually.

[21] At sixteen, Kajol began work on Bekhudi, which according to her was a "big dose of luck";[16] she was cast by him when she visited the studio of the photographer Gautam Rajadhyaksha, who also wrote the film's screenplay.

[26] Co-starring Shah Rukh Khan and Shilpa Shetty, the film saw Kajol in the role of Priya Chopra, a young woman who falls in love with her sister's murderer, unaware of his identity.

Consequently, she made a deliberate decision to sign up lighter films in which she would have roles of minimal importance and no intense dramatic efforts, including Hulchul, Gundaraj, and Karan Arjun—all released a year later.

[22] She gained wider public recognition for her role in Yeh Dillagi, a romance produced by Yash Raj Films and based on the 1953 American play Sabrina Fair.

[34] She starred as Sapna, a chauffeur's daughter who becomes a model and catches the interest of the two sons of her father's employers (Akshay Kumar and Saif Ali Khan).

[35] A financial success,[35] Yeh Dillagi proved to be a breakthrough for Kajol,[6] earning her a first Best Actress nomination at the annual Filmfare Awards.

[39] Kajol's next releases—Taaqat, Hulchul and Gundaraj—underperformed at the box office;[39] the latter two were her earliest collaborations with her future-husband, Ajay Devgn, and trade analysts linked the failure to their chemistry.

She played the comic role of Sanjana, a clumsy woman who travels from Paris to India in search of her philandering fiancé, but falls for another man (Ajay Devgn).

[99] In a year-end column, The Tribune's Madhur Mittal reported that Kajol had "emerged as the consummate heroine with her excellent emoting and sensational screen presence in each portrayal".

[100] Journalists speculated that the supporting role of the other woman of Ajay Devgn's character in Dil Kya Kare, Kajol's first release after marriage, would be "the acid test" for her.

[114] The following year, Kajol and her husband starred together in his home-production Raju Chacha, whose plot revolves on the love story between a conman and a governess of three children belonging to a wealthy family.

[153] The Economic Times' Gaurav Malini noted that Kajol's "simmering pace and ... recurring amnesiac spells, rather than getting repetitive, add compelling credibility to the story".

[163] Kajol's portrayal of Mandira, a Hindu single mother who marries a Muslim man with Asperger syndrome was praised by Indian and overseas critics.

[164][165] Rajeev Masand wrote positively of Kajol's sensitive performance,[166] while the Los Angeles Times found her to be appealing in an emotion-based role.

[169][170] In the same year, Kajol was the protagonist in Siddharth Malhotra's We Are Family, an adaptation of the 1998 American drama Stepmom, alongside Kareena Kapoor and Arjun Rampal.

[174] Mayank Shekhar singled out Kajol's performance as being better than Sarandon's,[175] and Rachel Saltz of The New York Times commented that "her naturalism gives the movie a genuine emotional kick".

[176] Kajol's next release that year, Toonpur Ka Super Hero featured her as Priya Kumar, a woman stuck in a cartoon world.

"[191] Dilwale emerged as a major commercial success, grossing more than ₹3.8 billion (US$44 million) worldwide, and ranks among of the highest-grossing Bollywood films of all time.

[193] Later that year, she made her debut as a producer with the Marathi period drama Vitti Dandu, co-produced by Ajay Devgn and Leena Deore, and exploring the relationship between a grandfather and his grandson.

[229] The following year, Kajol starred in a segment of the Netflix anthology film Lust Stories 2 and in Disney+ Hotstar's legal drama series, The Trial, an adaptation of the American show The Good Wife.

[232] In Do Patti (2024), Kajol played a Bihari police officer uncovering a domestic abuse case involving twin sisters (Kriti Sanon).

[240] She featured as a talent judge with husband Ajay Devgn and mother Tanuja in Zee TV's 2008 reality show Rock-N-Roll Family,[241] which she found to be a much tougher experience than that of in films.

[250][251] In 2012, Kajol was appointed as the brand ambassador of Pratham, a charity organization for children, and she featured in a short film on education and literacy, with the Hanuman Basti Primary School's students in Mumbai, to support it.

"[26] After portraying leading roles in a series of family dramas, Kajol showed her acting versatility with Gupt: The Hidden Truth (1997),[269][270] for which she was noted as being one of the first actresses of her era to play female anti-hero characters and becoming more popular than the male actors.

[85][271] Rajiv Menon credited Kajol as representing the joie de vivre of the 1990s,[2] and Khalid Mohammed described her as "a great packet of talent".

[277][278] Gautam Rajadhyaksha stated she was apathetic of hairstyles and clothes, and would be really happy if she was allowed to wear jeans, a white shirt, and a scarf every day.

[38] The journalist Kaveree Bamzai elaborated, "She hardly looks into the mirror, barely even glances at the set monitor, usually the crutch of every insecure actor, puts on make-up only under extreme duress, and ... never watches her old movies.

"[16] Comparing her to Shabana Azmi and Smita Patil, the producer Mahesh Bhatt observed that Kajol "may not have [their] earthy sensuality but she has that extra sparkle in her eyes and a kind of energy she generates on screen which make her incredible".

[286] In 2012, Kajol was placed at the fourth position by NDTV in the listing of "The Most Popular Actress of All Time", behind Madhuri Dixit, Sridevi and Meena Kumari, and Yahoo!