A pair of children, born within moments of India gaining independence from Britain, grow up in the country that is nothing like their parent's generation.

On a flight to Mumbai, Akshay meets with his wealthy ex-girlfriend, Sanjana, who is in the company of another male, Rajeev. He, a struggling artist, recalls how he met her in Cape Town and their moving in together. Differences crop up, and get worse, when he does not meet with her busy dad, leading to their taking different paths. After the plane lands they head out to their respective destinations - little knowing the danger that awaits them after the city experiences life-threatening heavy rains and floods.

Arriving in Mumbai with just a backpack and a guitar, Raunaq Kaul hooks up with Surinder Bhan, who introduces him to Charlie, the owner of 'Charlie Tango' nightclub. This is where Raunaq makes his start and achieves phenomenal success as a composer virtually overnight. He quickly regresses to a life of illicit drugs, including Charas, Cocaine, Ganja, smoking, and alcohol. Unable to perform, he goes for a medical check-up with Dr. Manu Rishi Kaul, and is told that he has lost his hearing in the right ear, while the left one is only partly functional. In order to avoid deafness, he must avoid loud music as well as try and keep off drugs, alcohol and smoking, and wear a hearing-aid. Unable to focus on his work, he alienates himself, gets into an argument, which results in an accident - taking away his hearing altogether. Depressed, refusing to communicate with anyone, he prepares a padded sound-proof room with hopes of recovering his hearing...

99 is an original story inspired by real events - well, very liberally inspired - it is more fiction than fact. It is the story of two men in two cities, who are bound by a common feeling of always being stuck at '99'. They never seem to make it to a 'century' - in life. It is an unpredictable and hilarious ride spread over two cities with colorful characters, unbelievable circumstances, small-time crooks, big-time conspiracies, fateful car crashes, a briefcase full of money... and a historical controversy brewing in the background!