Bollywood actresses who have enjoyed lengthy and successful careers—many lasting two decades or longer—demonstrating their versatility and enduring presence in the industry. Some of them have been romantically paired with both father and his son.
Several actresses from Bollywood have had the rare opportunity to be cast alongside both a father and his son throughout their acting careers. Below are some of the most prominent instances:
Madhuri Dixit:

Madhuri Dixit starred opposite Vinod Khanna in the films Dayavan and Maha-Sangram. Subsequently, she was paired with his son Akshaye Khanna in the movie Mohabbat.
Additionally, Madhuri Dixit appeared with Rishi Kapoor in movies such as Yaarana and Prem Granth. She also shared the screen with his son Ranbir Kapoor in the film Yeh Jawaani Hai Deewani during the item song “Ghaagra”.
Dimple Kapadia:

Dimple Kapadia collaborated on several films with Dharmendra, including Batwara and Shehzada. She also shared romantic scenes with Sunny Deol in movies such as Manzil Manzil, Arjun, Aag Ka Gola, and Narsimha.
Additionally, she had a romantic pairing with Vinod Khanna in Insaaf and was also cast alongside his son Akshaye Khanna in Dil Chahta Hai.
Sridevi:

Sridevi shared a romantic storyline with Dharmendra in Naakabandi. Furthermore, she was paired with his son Sunny Deol in films like Nigahein, Chaalbaaz, and Joshilay.
Amrita Singh:

Amrita Singh made her debut alongside Sunny Deol in the film Betaab. Six years later, she portrayed Dharmendra’s wife in Sachai Ki Taqat. She also had the distinctive opportunity to collaborate with Sunil Dutt, playing his wife in Kaala Dhanda Gorey Log, and later starred opposite Sunjay Dutt in Naam and Naam O Nishaan.
Hema Malini:

Hema Malini made her debut opposite Raj Kapoor in Sapno Ka Saudagar. Years later, she went on to romance his son, Randhir Kapoor, in the film Haath Ki Safai.
Shilpa Shetty:

Shilpa Shetty worked with Amitabh Bachchan in the movie Lal Badshah. She was also featured alongside his son, Abhishek Bachchan, in the film Phir Milenge, as well as in the song Shut Up and Bounce from the film Dostana.
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