Over the years, Shammi Kapoor has worked with many of the leading actresses of Retro-Bollywood. These are some of his most notable Leading Ladies (according to me).
Shammi Kapoor acted with Nutan very early in his career. They starred in Laila Majnu (1953). The young Shammi Kapoor and the fresh-faced Nutan made a lovely pair onscreen portraying eternal lovers Laila and Majnu. They acted together again in Laat Saheb (1967).
Helen and Shammi Kapoor first starred together in Miss Coca Cola (1955). Since then, they have starred together in multiple films. Each time they came together, they created magic. In fact, most of Shammi Kapoor's masti-ful dance numbers almost always include Helen accompanying him. I remember watching an interview of Helen, where she talked about the relationship she had with Shammi Kapoor. Every time they had a song together, they would compete to see who had the most fun.
Asha Parekh started out her career as a leading lady with Shammi Kapoor in Dil Deke Dekho (1958). Since then she has starred with him in Teesri Manzil (1966), Pagla Kahin Ka (1970) and Jawan Mohabbat (1971). In an interview, Asha Parekh talked about the relationship that she shared with Shammi Kapoor. She was very close to him and his first wife, Geeta Bali. She used to call him Chacha, which means uncle.
Just like Asha Parekh, Sharmila Tagore started out her career in Bollywood with Shammi Kapoor in Kashmir Ki Kali (1964), which instantly made her a popular actress. She later acted with Shammi Kapoor in An Evening In Paris (1967), which once again became an extremely successful film further establishing her as a Bollywood leading lady.
Rajshree acted with Shammi Kapoor in two films, namely Bhramachari (1968) and Janwar (1965). Just like Shammi Kapoor, Rajshree was known for her dancing ability as well as her acting ability. Needless to say, both Shammi Kapoor and Rajshree set the screen on fire!
In an interview, Shammi Kapoor mentioned that though he acted with several leading ladies during his day, he considered Asha Parekh, Sharmila Tagore and Rajshree as the easiest to work with. Apart from these three ladies, Shammi Kapoor shared the best musical hits in his career with Helen, while he started out his career with Nutan.