Summaries

Synopsis

"Kaalakaandi" is a Marathi slang for when things go disastrously wrong. The film is a dark comedy about life, death and karma.Rileen (Saif Ali Khan), a simple man who doesn't smoke, drink, sleep around or attend parties gets the shock of his life when his doctor confirms he has last stage of stomach cancer and might survive not more than 6 months. Rileen was getting treatment for an Ulcer, and it is ironic as his own father also died of cancer. Rileen lived a healthy life, with organic foods and lots of vegetables. The doctor tells him to do whatever makes him happy, meet his lawyer and put his affair in order.

The very next day is his brother Angad's (Akshay Oberoi) wedding, who gets a call from his sexy ex Selina (Amanda Rosario) the night before his wedding. Angad is marrying Neha (Amyra Dastur). Rakhi (Isha Talwar) is the photographer of the wedding and is showing too much interest in Rileen. Rileen is asked to drop Rakhi to her home.

Sick of his boring life, Saif drops acid (LSD) for the first time and experiences some weird stuff, and to top that, binge drinks the whole night, roams around with a transgender prostitute Sheila (Nary Singh) - hoping to see what's under her clothes, gets chased by a belly toting police and even dresses up like a transgender himself. Rileen becomes happy and decides to fulfill other things on his bucket list.While Rileen is roaming the streets with a transgender, Angad goes to meet Selina at her hotel room for a midnight sex romp. He is not started when Selina kicks him out when her boyfriend calls her from the hotel lobby.

Angad learns that Selina is just using him and feels guilty about cheating on Neha, his fiance. Angad meets Neha and talks to her. He learns that Neha is a very nice girl and both of them hug each other and get ready for the wedding.

Angad runs into Rileen on the streets, as he is dressed as a transgender. Angad and Rileen drive around at night, when Angad confesses to Rileen that he doesn't want to get married. Rileen tells Angad to break up with his fiance to her face. When Angad meets her, she is getting ready and Angad does not have the courage to call the whole thing off.

On the other hand, an urban couple Zubin (Kunaal Roy Kapur) and Tara (Sobhita Dhulipala) prepare for Tara to fly to New York for higher studies. Zubin wanted to get engaged to Tara, but she refuses that they don't have the time or the energy to deal with that right then.They meet their friend Ayesha (Shenaz Treasurywala), who is celebrating her birthday the night before with her toy boy / 'sex slave' at a high-end club but gets raided by the police for drugs. Due to the raid, Tara is going to miss her flight to NYC (which is in 2 hours), and she is desperate to escape the raid. She borrows the uniform from a bartender and uses that to give a slip to the police and escapes the bar with Zubin.

In the car, Zubin and Tara have a heated argument over Tara kissing a guy. While escaping, a car jumps a red signal and in trying to avoid it Tara loses control and hits a motorcycle, killing two people. Tara is shocked and wants to turn herself over to the police. But Ayesha and Zubin encourage her to catch her flight and escape the country asap.

The other protagonists, two gangsters Rahmat (Vijay Raaz) and Mafia (Deepak Dobriyal) are on the prowl to get filthy rich and plot to cheat their own boss, a Mumbai Hawala big shot Raza (Asif Basra) who controls the whole city. Rahmat and Mafia devise a plan to steal the protection money they collected for Raza, by claiming that someone stole it. They also witness Raza killing Ustad (Neil Bhoopalam) via 2 motorcycle borne assailants, after Raza congratulated him for serving him loyally for 25 years as his personal bodyguard.

Mafia's greed pushes him to kill Rahmat. Mafia convinces Rahmat that he will shoot Rahmat in the arm to show that the robbers shot at them while they tried to protect the money. But Rahmat has played poker with Mafia for years and knows that Mafia is bluffing. Rahmat calls Mafia on his bluff and threatens to shoot him saying that Mafia wants to kill Rahmat and keep all the money for himself. Mafia pleads that he is Rahmat's brother. As soon as Rahmat lowers his guard, Mafia shoots him down. He also shoots himself in the arm.

He then goes to Raza and reports the theft of collection money to the tune of 1 Crore. But Raza spots that Mafia's own wound was from a bullet, and his shirt has a matching hole in it (purely by coincidence). Raza accepts Mafia's story and lets him go.

Rileen meets the wedding photographer Rakhi (Isha Talwar) and tells his son too had a birthmark like her on his elbow. Rakhi asks him his name, but he states that "People just meet, tell each other their names and then go away, which is of no use". He also tells her about his growing cancer. Rakhi comforts Rileen and they kiss each other. On being asked "What does he mean to her?", she replies "I don't know!" He happily laughs and tells her his name is Rileen.

Zubin drops Tara at the airport, and she reluctantly goes in.Tara checks into her flight while Zubin asks her not to think of the horrific night. Tara feels very guilty and decides to approach the police and file an FIR, but the police dissuade her from doing so as the two guys who were killed in the accident were underworld assassins who killed Ustad. Tara meets Zubin, who had been waiting for her. Learning that he truly loves her, Tara proposes to Zubin and then kisses him.

Rileen marches into the marriage where everyone is dancing mindlessly along with Angad and Neha. Rileen dances along, takes out his gun and fires two shots in the air. One of the bullets strikes Mafia in the head, killing him, while the other hits Rileen's foot, prompting him to scream in pain.