These are the top ten rewatchable movies according to me.
Anand (1971): If you haven't seen Anand, you have missed out on a gem of Indian cinema. Absolute poetry in dialogues.
Amar Akbar Anthony (1977): Absolute illogical movie but the peak of masala films. Very enjoyable.
Veer Zaara (2004): One of the best romantic films of Bollywood. Romantic films generally loose stream after a few years but not this one.
Anbe Shivam (2003): Unfortunate flop but a delightful film. Kamal Hassan and Madhavan give delightful performance in this heartfelt movie.
Baasha (1995): Partly inspired by Amitabh's Hum, but way better than its source material. Highly entertaining.
Golmaal (1979): Hrishikesh Mukherjee movies are some of the most watchable movies again and again for its simplicity. Hilarious film with excellent performances.
Chak De India (2007): I believe one of the best sports movie of Indian cinema. It is inspiring, entertaining and thought provoking at the same time.
Munna Bhai MBBS (2003): Again a very delightful and thought provoking film. It gets better with each viewing.
3 Idiots (2009): Very well written screenplay. Makes you laugh and cry alternatively.
Piku (2015): You can't make a better film on constipation. Feel Good film which makes you chuckle and yet feel connected with the characters in an emotional level.