Lucy (Arquette) is a young woman who works at a restaurant in Manhattan. She is constantly annoyed by her gambling, egotistical bosses. She has an ambition to be an escape artist, specifically a modern female version of Harry Houdini, with her best friend, Vivian (Balint) as her assistant. Lucy also collects anything that once belonged to Mrs. Houdini.
The movie starts with Lucy questioning who the new bartender (Bowie) is. She finds out his name is Monte, he's from Britain and will tell any lie in order to get a woman to marry him. He makes it clear he only wants to marry because he is in dire need of a green card, because if he doesn't and has to go back to Britain, he will surely die. The two chat, with Monte desperately asking Lucy out for breakfast, even though Lucy doesn't want to.
Later on, Lucy is practising an escape trick when she loses her balance and becomes trapped by the noose she was planning to escape from. Her wrists and ankles are both cuffed, meaning Lucy can't free herself. She cries herself to sleep after having not been able to reach the key that unlocks the cuffs. She is awoken in the morning by a phone call. She struggles to answer it but manages to by kicking the phone onto the ground so she can hear it. It's Monte wanting to take her out for breakfast, having found her number in the Yellow Pages. Lucy begs him to come to her apartment to untie her. He frees her legs and unites the noose but will only free her hands on the condition that she marries him. Lucy, unsettled, declines, so Monte handcuffs Lucy to himself and the bed before falling asleep, with an upset Lucy following suit.
Vivian enters the apartment the following morning to find Monte and Lucy asleep on the bed, handcuffed. Vivian unlocks Lucy but leaves the handcuffs on Monte. He later arises and eats a marshmallow for breakfast whilst the girls whisper in the bathroom about who gets to sleep with him.
Later on, Viv and Lucy ride to an antique shop where Lucy has her eye on Mrs. Houdini's wedding ring. Lucy will do anything to have it, but is unable to purchase it, as she doesn't have the $5,000 to pay for it. Lucy wonders how she can get the money. She decides to rob the restaurant after her bosses, Dante (Gregory) and Cecil (Henry) once again decide to fine the waitresses if they don't sell enough desserts. Monte is also present at the meeting, with one of his hands still cuffed.
Vivian goes to the restaurant to tell Lucy some big news: a designer is interested in meeting Viv to discuss her line of lingerie. The only problem is, Viv can only meet with the designer the following day at 3:00. This is a problem because Lucy has an audition for her escape trick, and Viv is her assistant. After an argument, Vivian storms off to go and talk to Monte, who's serving at the bar. Jealous, Lucy unlocks Monte from the handcuff and agrees to go out with him if he'll be her assistant at the audition; he accepts.
Monte has his doubts about Lucy, so he strikes a deal with Jeanette (Matlin), a deaf colleague: Jeanette will marry him if he pays her $10,000. This leads to a conversation Monte has on the phone with his friend. Lucy overhears the conversation and decides to eavesdrop. He explains to his friend his intention to rob the restaurant, and asks his friend to help, who declines.
Lucy confronts Monte while they are waiting for her turn at the audition. Both become frustrated because they both want to rob the restaurant at the same time. Lucy is called up and begins her escape routine. Unfortunately, the audition goes disastrously as she cannot find the key to free herself. Lucy is obviously upset so Monte takes her to a bar where they discuss who's going to rob the restaurant. They can't work together, as that would mean splitting the money, and Monte needs it all to pay Jeanette. Monte comes up with another plan: he will help Lucy rob the restaurant if she marries him. This way, Monte won't need the $10,000 to pay Jeanette.
Lucy begins to cry again so Monte tries to cheer her up by talking about Mrs. Houdini. Lucy, still upset, explains that Mrs. Houdini was vital to Harry Houdini's escape routines: before Mr. Houdini commenced with his trick, Mrs. Houdini would kiss him and transfer the key he needed to escape from her mouth to his. Lucy's mood has improved somewhat after this so the two walk down the street and discuss the possibility of sleeping together. Monte wants to, but Lucy declines and explains Viv was hoping to sleep with him first. With Viv in mind, he suggests that a third person that doesn't work at the restaurant and wouldn't be recognised would be ideal for the robbery. Lucy agrees and the two head to Vivian's apartment, where she's working on her 'self-defence bra'.
It's later on when the trio discuss the plan: at 12:00 AM, Viv will enter the restaurant and demand money, which she will take from the register. To appear more threatening, she will carry a gun which fires blanks. It's vitally important that it happens before the 12:30 AM drop. Monte and Lucy will create some clever diversions so that the guests will be on edge. At 11:59, they will drop a loud set of glasses to really unsettle the guests; seconds later, Viv will enter. Viv reluctantly agrees and takes the gun from Monte.
At 11:59, Monte and Lucy drop the champagne bottles and glasses... But Viv doesn't show up. Thinking she has dropped out, Monte storms off, and Lucy follows. She finds him in the freezer causing havoc and messing the room up. With adrenaline rushing through him, he makes out with Lucy. As it turns out, Viv had a flat tyre on her bike, so by the time she turns up in a disguise to commence the robbery the guests are calm and don't take her seriously. She makes threats but the guests laugh at her, so she pretends she's a performing artist and the stunt was part of her act.
In the freezer, Lucy flees the room, leaving Monte confused. She tracks down Vivian, who explains what happened. The situation is desperate and 12:30 looms, so Viv fires the gun, exclaiming, 'Sorry, I guess I wasn't kidding... Money. Now. All of it.' Jeanette, who works at the register, can't understand Vivian because the disguise is covering her face. Annoyed, Viv presses a button on her bra, which causes two knife-like spikes to stick out of it. Jeanette is fascinated and happily hands over a bag of money. Lucy and Monte leave the restaurant and later all three of them can be seen throwing money into the air, celebrating.
Expecting Lucy to uphold her side of the deal, Monte heads to the Register Office and waits for her. Meanwhile, Lucy heads back to the antique shop to buy the ring, only to find it has been sold. She heads over to Viv's apartment to mope. Viv's in a cheerful mood, however: since the robbery, companies have been calling her about her 'self-defence bra'. Lucy doesn't share the enthusiasm. Viv asks if she and Monte tied the knot. Lucy realises she completely forgot, so she and Vivian rush to the Register Office.
The girls arrive and Monte whisks Lucy away, but they are not able to marry because she left her I.D. at Viv's apartment. There is simply no time to get married any other day, so Monte leaves in anger. The two girls leave, too, and Lucy, full of guilt, confesses to Vivian that she made out with Monte. The two talk about him before deciding to head to a bar and get drunk.
Monte, meanwhile, is at the restaurant when Cecil and Dante approach him. It is revealed that Monte didn't need to get married to get his green card, but because he made a $2,000,000 bet with Cecil and Dante. We also learn that Monte has a terrible gambling problem. He manages to convince them to give him another chance, and they make another bet: Lucy will have one minute to escape from a straitjacket, hanging upside down, with her feet cuffed, inside a locked canvas bag, underwater (In Cecil and Dante's giant aquarium at the restaurant). If she is unable to, Monte will owe them $4,000,000, or, he will undergo plastic surgery to make himself look like Dante.
Of course, Monte can't win without Lucy's help. He arrives at Lucy's apartment, where the two girls are asleep. He wakes them up and discovers they have serious hangovers. Worried that they won't help him, Monte makes up a story, 'Cecil and Dante know about the robbery... I don't know how they found out... There's still hope. I made a deal- a bet-a bet with Cecil and Dante: if we win, they drop all charges, like nothing ever happened... [If we lose,] 20 years hard labour'. Vivian and Monte believe that they can train Lucy, but quickly, for the stunt is to be performed the following night. Lucy trains for hours, and before long, the three fall asleep, exhausted. Vivian wakes up in the early hours of the morning and leaves, which, in turn, causes Monte and Lucy to wake up. Lucy wants to get up and train, but Monte convinces her to stay, and the two make love in Lucy's apartment.
Later in the morning, Lucy is out shopping and sees Cecil and Dante driving past in a taxi. She tries to avoid them, but they drag her into the vehicle so they can rant about their excitement for the bet. After a bit of chatting, Lucy finds out that Cecil and Dante don't know who committed the robbery, even though Monte told her they knew. She discovers that Monte will have to pay Cecil and Dante $4,000,000 (or get plastic surgery) if he doesn't win the bet, even though Monte told her they'd go to jail if the bet was lost. Lucy is visibly shocked and asks the driver to stop before climbing out of the taxi.
It's the night of the bet and Monte is nervous, particularly because Lucy hasn't showed up. Monte learns that Cecil and Dante told her the truth about the bet. He now doubts that she will show, but begs the two men to stall the audience until she comes, so they do. Lucy finally shows up, surprising Cecil, Dante, and Monte. After an awkward arrival, she puts on the straitjacket, has her legs cuffed, and is almost in the canvas bag when Monte interrupts, wanting a 'goodbye kiss'. Lucy, still angry at him, refuses, until she sees he has Mrs. Houdini's wedding ring between his teeth.
Lucy is locked in the bag, suspended upside down, and dropped into the water. She appears to be struggling to escape when several gun shots fire. It's Vivian, dressed in a red disguise but with the same black veil covering her face. She presses her 'self-defence bra' and the spikes once again stick out. She demands money and the audience give it to her whilst Monte stares in shock. Jeanette also gives her two bags of money from the register.
When Viv leaves, the attention turns back to Lucy. The canvas bag is still in the water. Monte- aware that if he tries to save her, he will lose the bet- jumps into the water, before finding out that the bag is devoid of Lucy. The audience is confused until they find her on the second level of the restaurant, dripping from the water but otherwise fine.
Later on, Monte is still somewhat damp but approaches Lucy nonetheless. She's less angry with him since he risked $4,000,000 to save her, but she shakes his hand and prepares to leave him for the last time. Monte calls her back and asks if she will go out with him the following day, but this time, it's for real. The two kiss before Lucy leaves. Outside, Viv is waiting by two new bikes from Cecil and Dante and the movie ends with the two girls riding down the dark street.David Bowie as Monte
Rosanna Arquette as Lucy
Marlee Matlin as Jeanette
Eszter Balint as Vivian
Buck Henry as Cecil
Andre Gregory as Dante
Iman and Julian Lennon have brief cameos in the movie.
The movie was released to VHS in 1992.
Reviews of the movie were mostly negative. Empire magazine gave the movie one star out of five, calling it "an unbearably protracted dud". Variety magazine called the movie an "uninspired, poverty row production" and lamented the mis-casting of Bowie in the lead role. A review by The New York Times is positive and approves of the film's casting. TV Guide gave the movie 2 stars out of 5.