[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,[5] 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.

[183] She followed it with a second hiatus upon the birth of her son in 2010 although she provided voiceover to the opening credits of the Hindi version of the fantasy film Eega, which released in 2012.

"[191] Dilwale emerged as a major commercial success, grossing more than ₹3.8 billion (US$43 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 investigating 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".