Jackie Brown (1997)
The middle-aged stewardess Jackie Brown smuggles money from Mexico to Los Angeles for the arms dealer Ordell Robbie. When she gets caught by the agents Ray Nicolet and Mark Dargus with ten thousand dollars and cocaine in her purse, they propose a deal to her to help them to arrest Ordell in exchange of her freedom. Meanwhile Ordell asks the 56-year-old Max Cherry, who runs a bail bond business, to release Jackie Brown with the intention of eliminating her. Jackie suspects of Ordell's intention and plots a complicated confidence game with Max to steal half a million dollars from Ordell.
Jackie Brown is the name of a flight attendant who gets caught smuggling her boss's gun money on the airline she works for. Luckily for her, Fed Ray Nicolet and L.A. cop Mark Dargus decide to team up in order to arrest the arms dealer she works for, whose name they don't even know. Here's when she has to choose one way: tell Nicolet and Dargus about Ordell Robbie (the arms dealer) and get her freedom-except that if Ordell suspects you're talking about him, you're dead-or keep her mouth shut and do some time. That's when she meets Max Cherry, her bail bondsman, a recently separated, burnt-out man in his late fifties, who falls in love with her. Then Jackie comes up with a plan to play the Feds off against Ordell and the guys he works with-Louis Gara and Melanie Ralston, among others-and walk off with their money. But she needs Max's help. No one is going to stand in the way of his million-dollar payoff.
Forty-four-year-old flight attendant Jackie Brown gets caught with gun dealer Ordell Robbie's money and to get the ATF off her back she sets up Ordell with her new friend, a bail bondsman named Max Cherry. But what the ATF doesn't know, is that they are part of her wild plan to get Ordell's half million dollars and get off scot-free. However, she has to do it under the noses of both Ordell, the ATF man and a local cop. What she doesn't know is Ordell's blonde beach bunny wants the money for herself as does Ordell's ex-con friend.
A middle-aged woman finds herself in the middle of a huge conflict that will either make her a profit or cost her life.
- Los Angeles,1995. Jackie Brown (Pam Grier) is a flight attendant for a small Mexican airline called Cabalas Airlines which flies only from L.A. to Cabo San Lucas, the latest step down for her career. Despite the low pay, the job enables her to smuggle money from Mexico into the United States for Ordell Robbie (Samuel L. Jackson), a gun runner under the close watch of the ATF.
One day, Ordell learns that another of his workers, Beaumont Livingston (Chris Tucker), has been arrested. Fearing that Livingston will become an informant in order to avoid jail time, Ordell arranges for his $10,000 bail with bail bondsman Max Cherry (Robert Forster). That same evening, Ordell promptly leads Livingston to his death by tricking him into getting into the trunk of a stolen car where Ordell shoots him to death.
Acting on information Livingston had indeed shared after his arrest, ATF agent Ray Nicolette (Michael Keaton) and LAPD detective Mark Dargus (Michael Bowen) intercept Jackie as she arrives in the United States with Ordell's cash and some cocaine that Brown was unaware was stashed along with the $30,000 cash. She initially refuses to cooperate with Nicolette and Dargus, so Jackie is sent to jail on possession of drugs with intent to sell. Sensing that Jackie may be just as likely to inform as Livingston had been, Ordell goes back to Max Cherry and sets out to arrange Jackie's bail so he can plot to kill her too once she is released.
That evening, Max Cherry arrives at the jail to pick Jackie up and, only partly masking his physical attraction, offers to buy her a drink and help determine her legal options. Over drinks at a local bar, Jackie senses an attraction that Max has on her, but reminds him that she is not interested. After dropping her off at her apartment, Jackie steals Max's gun that he kept hidden in his glove compartment.
Later that night, Ordell arrives at Jackie's apartment apparently intending to murder her. Jackie pulls out the gun she stole/borrowed from Cherry and she holds him at gunpoint. Jackie barters a deal with Ordell whereby she will pretend to help the authorities while still managing to smuggle $500,000 of Ordell's money out of Mexico, enough to allow him to retire and flee to some distant country and retire. To carry out this plan, Ordell employs a woman he lives with, "my little blond surfer girl"; a drug-addicted beach bunny named Melanie Ralston (Bridget Fonda), plus his friend, Louis Gara (Robert De Niro), a former cellmate whom has shacked up with him. Ordell also uses a naïve Southern girl, Sheronda (Lisa Gay Hamilton) as his co-conspirator to give him an alibi for when the transaction will take place.
The following day, Jackie meets at LAPD headquarters with Agent Nicolette and Detective Dargus to arrange a sting to catch Ordell. But Nicollette and Dargus are both unaware that Jackie and Ordell plan to double cross them by diverting the actual money before the authorities make an arrest. Unbeknownst to the others, Jackie plans to deceive them both with the help of Cherry in order to keep the $500,000 for herself. However, in another twist, Melanie tries to convince Louis to steal the $500,000 that Jackie will hand over to them and flee the country with the money for themselves. Though Louis agrees, he does not trust Melanie for she might take all the money for herself out of greed, while Melanie clearly suspects likewise about Louis.
After a dry run, during which Nicolette could observe the operation, the stage is set for the actual event. Told from three different viewpoints (a nod to 1950s film noirs) the exchange takes place in a large shopping mall near Los Angeles (the Del Amo Fashion Center).
Jackie's version: At the mall, Jackie enters the Billingsley department store where she buys a new suit and enters a dressing room. Her real intention is to swap bags there with Melanie and Louis, supposedly passing off the $500,000 under Nicolette's nose. Instead, she gives Melanie only $50,000 and leaves the rest behind in the dressing room for Max Cherry to pick up. Jackie then feigns despair as she leaves the department store and into the mall where she calls Nicolette and Dargus out from hiding and claims Melanie took all the money and ran.
Louis and Melanie's version: Louis meets Melanie at Ordell's beachfront house while Ordell goes to a local bar-restaruant, called the Cockatoo Bar with Sheronda to have an alibi to his whereabouts for the day. Melanie gets on Louis case from the start when they are late for the rendevouz because Louis finds Melanie wasting time by getting high in the bathroom with smoking a basepipe. During the drive to the mall, the stoned Melanie annoys Louis more by playing loud rock music over the van radio. During the switch, Melanie enters the dressing room at Billingsley's with a brown bag of beach towels to make the switch while Louis waits outside, where he catches a glimpse of Max Cherry standing nearby. Melanie exits the dressing room with the other brown bag containing part of the cash. In the parking lot, Melanie gets on Louis' nerves more and more, which finally leads him to shoot and kill her while making their escape after she mouths off one too many times.
Max Cherry's version: Max arrives at the mall alone and at the Billingsley's department store where he eyes Jackie from a distance and tries to hide when Louis and Melanie walk by to make the switch, but Louis catches a glimpse of him as they walk by. After Louis and Melanie leave the store, Jackie, pretending to be in dispair, pays for her new business suit and leaves the store. When Jackie leaves, Max approaches the sales clerk and claims that his wife left a bag in the dressing rooms for him, which Max picks up the bag containing the $500,000 cash and quietly leaves the store where he drives to his office to stash the cash before driving home.
Across town, Louis then picks up Ordell from the Cockatoo Bar where he soon discovers that Louis has only $40,000 in the bag (Melanie having kept $10,000 for herself after being tricked into doing so by Jackie, which is apparently left on her dead person). Then Ordell realizes that it was Jackie who took his money, and in anger, a suspicious Ordell kills his friend Louis. He is also concerned about the involvement of Max Cherry, having been told by Louis that he spotted Max in the store before the pickup.
At police headquarters, Agent Nicollette is angry with Jackie for what transpired during the pickup (Jackie apparently told him that the money that she was carrying was only $50,000, not the entire $500,000 from Ordell's secret account in Mexico). Nicollette tells Jackie about finding Melanie in the mall parking lot with $10,000 on her, and about finding Louis a short distance away in his van. Nicollette tells Jackie that she has only one more chance to cooperate with them to catch Ordell and find the rest of the money.
That evening, Ordell goes to the Cockatoo Bar where Max is and pulls a gun on him and demands that he help him find Jackie who has his money. Lured back to Max's office, where Jackie is said to be frightened and waiting to hand over his money, Ordell arrives armed and dangerous. Jackie suddenly yells out that Ordell has a gun and he is shot by Nicolette, who was hidden in another room.
Three days later. In the clear with the law and in possession of the $500,000, Jackie decides to leave town for a while, and she invites Max to run off with her. Max is tempted, clearly in love with her as they kiss, but he declines to go with Jackie for reasons that are left unclear.
Note: There are a number of hints during the movie given by Cherry in his dialogue with Jackie about why he makes the choices he makes and does not act out of greed. Some include Max's wanting to get out of the bail bond business and find something else to do to being too old to start a new adventure in life ("I'm just tired in general...."), but his reasons for turning down an offer to run off with a woman he is obviously in love with remains intentionally ambiguous at the film's closing.