- Focusing on life, death and karma, this dark comedy follows three parallel tracks - a man who discovers that he is a terminally ill, a woman seeking redemption and two goons with major trust issues.
- Unfolding through a course of a night in Mumbai, Kaalakaandi showcases three parallel tracks -- a man who discovers he has terminal illness decides to let go of his principles and live a little; a woman involved in a hit-and-run seeks redemption and two goons must decide if they can trust each other.
- "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 and 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. Rakhi (Isha Talwar) is the photographer of the wedding and is showing too much interest in Rileen.
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 - hoping to see what's under her clothes, gets chased by a belly toting police and even dresses up like a transgender himself. 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 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 to fly to New York for higher studies but meet their friend Ayesha (Shenaz Treasurywala), who is celebrating her birthday the night before with her toy boy aka '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, 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. While escaping, a car jumps a red signal and in trying to avoid it, Tara runs over a guy on a motorcycle. 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. Zubin drops Tara at the airport and she reluctantly checks in. But she doesn't board the flight and goes to the local police station instead. The police inspector tells Tara that the 2 men who died (car and bike) were shooters of the underworld (the ones who killed Ustad. The police was chasing them when they met with the accident with Tara.
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) after Raza congratulated him for serving him loyally for 25 yrs.
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. He calls Rahmat 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 brother. As soon as Rahmat lowers his guard, Mafia shoots him down. He also shoots himself.
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 joins the wedding celebrations with Angad and fires a shot in the air while dancing. The bullet goes ballistic and comes down at the precise spot where Mafia is sitting and celebrating his theft. Mafia dies on the spot.
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