Two common criminals get more than they bargained for after kidnapping the wife of a corrupt real-estate developer who shows no interest in paying the $1 million dollar ransom for her safe return.
Margaret 'Mickey' Dawson is a housewife, whose husband Frank (Robbins) has been embezzling millions for years without her knowledge. Career criminals Louis and Ordell catch wind of his scam and figure if they hold Mickey for ransom, Frank would have no choice but to pay up big, without realising Frank is head over heels for his mistress Melanie and doesn't want his wife back.
In Detroit, 1978, Louis is robbed of 27 dollars by a big bully. His friend Ordell helps him get more than his money back, by running over the mugger with his car. But the two of them have bigger plans that will make them super rich.
Stoic socialite Mickey Dawson (Jennifer Aniston) becomes the target of an ill-planned kidnapping plot by a pair of fumbling ex-cons, Ordell Robbie (Yasiin Bey) and Louis Gara (John Hawkes), looking for a get-rich-quick scheme. Ordell had come across a piece of information about how Mickey's husband Frank was not paying his taxes and was depositing his money in an offshore account. Through their friend they know that Frank has been depositing this money in a numbered account in the Bahamas.The plan was to kidnap Mickey and force Frank to pay some of that illegal money to the kidnappers.
Mickey takes her son, Bo, to play tennis at the country club. Louis is also there just to take a look at her, but actually happens to talk to her briefly when they meet in a corridor. A man named Marshall Taylor, a married man who does some work for Frank, is trying to have an affair with Mickey, but she is not interested.
When Ordell and Louis find out that both Frank and the son are going to be away for a week to Freeport, they decide it's time to proceed with kidnapping. They arrive at the house, masked, and take Mickey by surprise in the kitchen. She drops a glass and cuts her foot. Other than that, all goes according to plan.Marshall Taylor (Will Forte) is Frank's business partner & has the hots for Mickey. On the day of the kidnapping, Frank was away on a business trip with their son Bo (Charlie Tahan) & Marshall comes over hoping to have sex with Mickey. But Ordell and Louis knock him out.Upon regaining consciousness, Marshall decides not to report the kidnapping to the police & instead pretends that he has been in a car crash, to explain his head injury.
Ordell finds out from his contact in the Bahamas, that Frank is there with a mistress.However, things quickly become complicated for the duo when they find out her wealthy husband, Frank (Tim Robbins), refuses to pay the ransom as he was on the cusp of filing for divorce to make way for his younger mistress, Melanie Ralston (Isla Fisher). Frank has just filed for divorce and the papers would be reaching home to Mickey, while Frank is in the Bahamas.The two kidnappers have to figure out how to quickly turn the tables around on their predicament before their time runs out.Mickey is locked up in a bedroom at Richard's, who is a Nazi admirer, and she has to wear a blindfold so she can't see the kidnapper's faces when they give her food, or she has to go to the bathroom. Louis bandages her foot caring and professionally.
Louis helps Mickey when she is harassed by their 3rd partner Richard (Mark Boone Junior), who is also a bit of a pervert as he spies on Mickey from holes in the door of her bedroom and bathroom. Mickey finds out and to deter Richard, she jams a lit cigarette into his eye through the peephole.They have a bit of a bond. Louis tells Mickey that Frank has a mistress in the Bahamas and has a personal bank account with over a million dollars in it. Frank has been stashing money into this account, so that he doesn't have to pay alimony to Mickey when he finally divorces her.
Ordell and Louis phone Frank and ask for a million dollars to be deposited into a numbered bank account. Melanie convinces Frank to call their bluff. Frank & Melanie stop taking any calls from the kidnappers, & in the meantime Marshall returns to Mickey's home to remove all traces of him ever being there. While coming out of the house, Marshall is spotted by Richard, who is also local police cop & is keeping an eye on the premises. He had come by to see if Marshall had died. Richard wants to take Marshall in, but he escapes, riding his car really hard.
Ordell is angry at Frank not paying up & wants to cut up Mickey's finger to send to Frank as a message. Louis has a thing for Mickey & stops Ordell from doing anything. He convinces Ordell to go to the Bahamas himself to confront Melanie & Frank. Ordell travels to the Bahamas & meets Melanie. Melanie explains to Ordell that them kidnapping Mickey saved Frank a $100,000 in alimony every year, as he was divorcing her anyways. She offers $ 100,000 for Ordell to walk away or more if he kills Mickey. Ordell hooks up with Melanie.Ordell calls Richard & tells him to kill Mickey when Louis is away from the house. Ordell talks to Richard only, and orders him and Louis to bring Mickey back to her house but tells Richard to go back in and kill her afterwards, without Louis knowing it.
Richard send Louis away on the pretext of getting a car to return Mickey to her home (saying that Ordell has got the money from Frank). Louis returns just in time to see Richard trying to sexually assault Mickey & hits him & escapes with Mickey. Richard shoots at Louis, & a cop car picks up the shots and calls for back up. Richard is shot by cops who enter the house.
Louise drops Mickey off at her house. Mickey tries to convince Louise that maybe Ordell was lying about being paid by Frank, But Louise doesn't pay heed to it. Mickey is back in her home. She reads the divorce papers and goes out to see some old work friends but gets tired of her old life.The next day Frank comes back from the Bahamas & is surprised to see Mickey at the house & alive. Mickey threatens to expose Frank's illegal business activities with which he has been stealing money & stashing into his personal account in the Bahamas, in return for a fair deal on the alimony.
Mickey goes to see Louise, only for him to show her that Melanie is now with Ordell. Melanie is oddly hostile towards Mickey, but Mickey plays it cool. She tells the group that Frank is going to divorce her & is planning to marry Melanie. The group prepares to kidnap Melanie now.
