1 Hum Kisise Kum Nahin (1977)
Nasir Hussain's teenager classic was replete with the fusion of Western rhythms and Eastern sentimentalism. RD Burman came up with some of his best work in songs like 'Kya hua tera wada' and 'Tum kya jaano'. But the high point of the film was the medley during the singing competition, with Rishi Kapoor sizzling it up in pearly white bellbottoms and a glitzy trumpet.
2 Mr. India (1987)
What do you do when you accidentally anger an already angry heroine? Cue a medley of classic Laxmikant-Pyarelal numbers to cool down the hot headed Sridevi. Add a bunch of adorable kids trying to get their football back, and you understand why it is one of the more memorable songs from the film.
3 Patthar Ke Phool (1991)
When it comes to having fun onscreen, no one matches up to Salman Khan! A reminder of his very early years in Bollywood, Patthar Ke Phool was also the debut of a very beautiful Raveena Tandon. This song has the 'bhai' spoofing some iconic characters from the Raj Kapoor stable.
4 Gambler (1995)
Alright then. This is, technically, not a medley. Yes, it does not belong to this list. But it's GOVINDA! Any list with dance numbers cannot ignore Govinda. From wanting to date Madhuri Dixit to getting into a fight with Mike Tyson, the actor goes on the most zeitgeisty wish list of the 90s. The most natural dancer in Bollywood, his antics and pitch perfect pronunciation of crazy lyrics (Devang Patel) make this song instantly viral to this day!
5 Padosan(1968)
This one is certainly a medley. Two different Indian classical styles competed for superiority in the background, while two crazy, maniacal actors ran amok on screen. Undoubtedly, Kishore Kumar sang for himself, but Manna Dey voiced the brilliant South Indian 'masterji', Mehmood. What followed was one of the most memorable, and hilarious, singing contest in Hindi cinema.
6 Maine Pyar Kiya (1989)
What do you do when you have to confess your love with your parents, and a whole battallion of relatives, watching? Well, you turn to Bollywood songs. The baap of all antakshari songs in Hindi cinema, Sooraj Barjatya brought the tradition of antakshari to Indian cinema in Maine Pyar Kiya. Adorable, nerdy, and too cool to miss.
7 Chashme Baddoor (1981)
It is not just heroes who get to sing songs. Ravi Baswani's Jai does a brilliant job of reimagining his potential love story with Deepti Naval like a typical filmy director. His dream sequence is filled with the typical romantic numbers. The show stealer is both the actors spoofing some iconic stars; from Dev Anand and Sunil Dutt to Nargis and Madhubala.
8 Mujhse Dosti Karoge
Of course we had to have a Yashraj film on this list! The people who taught the world of the scale of Indian weddings, Yash Raj got the mehendi ceremony just right in this forgettable Hrithik-Kareena-Rani triangle. From overjoyed aunts to annoyingly friendly cousins, the composers had everyone singing the improvised versions of Bollywood classics.
9 Jo Jeeta Wohi Sikandar (1992)
This was the 'Grease' of Bollywood. Composed by Jatin-Lalit, Mansoor Khan's film had a symphonic soundtrack that is easily among the best of the 90s decade. Among gems like 'Pehla nasha' and 'Yahan ke hum sikandar' was also a peppy medley that is performed at the inter-collegiate competition.
10 Rock On
It is hard to pick out just one song from this surprisingly good soundtrack. But, if we have to, the final concert of 'Magik' takes the prize. The soundtrack of the film builds it up to the crescendo of 'Sinbad the Sailor' followed by the fan favourite 'Tum ho to'.