She also made an impression in Indian parallel cinema such as Mandi (1983), Rihaee (1988), Drishti (1990) and Suraj Ka Satvan Ghoda (1992). These performances further established her profile in Indian movies alongside her arthouse film contemporaries Rekha, Shabana Azmi, Smita Patil and Dimple Kapadia. Despite this, Gupta never had a major commercial hit and found it difficult to find more dramatic roles: Her appearance in Hindi movies was especially noted in the satirical movie, Jaane Bhi Do Yaaro in which she played the role of a secretary to Pankaj Kapoor. She also starred along with Madhuri Dixit in Khalnayak (1993); she was featured in the popular song "Choli Ke Peeche" in the movie. She has made television movies, Lajwanti and Bazar Sitaram (1993), which won the 1993 National Film Award for Best First Non-Feature Film. In 1994, Gupta's breakthrough came in the acclaimed drama Woh Chokri as a recently widowed daughter-in-law; this performance won her a National Film Award for Best Supporting Actress. In 2017, Gupta made headlines when she shared a post on Instagram asking for work: "I live in Mumbai and working as a good actor looking for good parts to play." Fed up with the lack of roles being written for middle-aged women in Bollywood, Gupta later reflected, "After that Instagram post, I got many offers -- five, in fact, and I accepted all of them. There is no shame in saying you don't have work." One of the offers she accepted was Amit Sharma's comedy-drama Badhaai Ho (2018), which emerged as the ninth highest-grossing Bollywood film of 2018. Her performance as a middle-aged pregnant mother earned widespread critical acclaim, with various critics and publications citing her performance as the film's highlight and one of the best of her career. Rajeev Masand credited Gupta for bringing "real empathy" to the part, while Saibal Chatterjee of NDTV described her portrayal as "outstandingly measured." Acting opposite Ayushmann Khurana as her son, Gupta received various accolades for her performance including the Filmfare Critics Award for Best Actress, the Screen Award for Best Actress (Critics), and the BFJA Award for Best Supporting Actor - Female. At 60, she became the second-eldest Best Actress nominee in Filmfare Award history after Sharmila Tagore. In 2020, Gupta appeared in Ashwiny Iyer Tiwari's sports comedy-drama Panga, and has reunited with Ayushmann Khurana for Shubh Mangal Zyada Saavdhan, with the latter earning her a Filmfare