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"That phone call I got, it came from outside high walls and fancy gates; it comes from a place you know about, maybe, from the movies. But I come from out there, and everybody out there knows: everybody lies. Cops lie, newspapers lie...your parents lie. The one thing you can count on: word on the street. Yeah, that's solid."—Charlie Barrett
A Black Comedy Psychological Thriller, and the feature film debut of TV director Peter O'Fallon, telling (with heavy amounts of Flashbacks) the tale of two kidnappings and the web of betrayal that spawned them.
When Impoverished Patrician Avery Chasten (Henry Thomas) finds that his sister Elise (Laura Harris) has been kidnapped and the Police Are Useless, he turns to his three lifelong friends, Elise's boyfriend Max (Sean Patrick Flanery), Nouveau Riche blusterer Brett (Jay Mohr), and medical student T.K. (Jeremy Sisto) to get the ransom by any means necessary.
Their plan: to abduct retired crime boss Charlie Barrett (Christopher Walken) and force him to pay the ransom. With the unwitting help of their friend Ira (Johnny Galecki), who provides his parents' palatial home in the belief that they plan to spend the weekend playing poker, they successfully kidnap Charlie and force him to use his underworld contacts to get in touch with the kidnappers.
As Charlie's right-hand man, ruthless thug Lono Veccio (Denis Leary), simultaneously searches for Elise's kidnappers and for Charlie's, the captive crook plays a game of mental cat-and-mouse with his captors, learning the real story behind the kidnapping of Elise while working to find their weak spots and convince them to set him free.
Provides examples of the following tropes:
- Abusive Parents: Ira's parents (or, at least, his father) are implied to be emotionally abusive.
- Affably Evil: Charlie.
- The Alcoholic: Charlie, which becomes a plot point, as his vitamin K deficiency inhibits his blood clotting.
- All Devouring Black Hole Loan Sharks: Avery owes them a pile of money.
- Badass Grandpa: Charlie.
- Big Fancy House: The setting for the bulk of the film.
- Brick Joke: "It was your idea, dunsky."
- Chekhov's Gun: Avery's sports betting and Max's ability to navigate Harlem.
- Deathbringer the Adorable: The Widowmaker, who is just an obnoxious blackjack dealer.
- Do Not Call Me Paul: That's "Charlie Barrett," not "Carlo Bartolucci."
- Downer Ending: Avery is revealed to have had his own sister kidnapped by the mob to pay off his debts, while Max and Elise doublecrossed everyone and took off with the money. Charlie and Lono track the latter two down and murder them to get the ransom back.
- The Dragon: Lono.
- Dumb Muscle: Heckle and Jekyll.
- Even Evil Has Standards: Charlie says that you should never lie to your friends. Lono stands up to an abusive husband.
- Evil Debt Collector: Heckle and Jekyll.
- Fake Nationality: Christopher Walken and Denis Leary as "Carlo Bartolucci" and "Lono Veccio."
- Finger in the Mail: The kidnappers sent Elise's father her finger in a box. Turns out, it wasn't her finger.
- Fingore: To motivate him, the Five-Man Band decides to do to Charlie whatever the kidnappers do to Elise. The first thing they do is cut off his finger.
- Five-Man Band:
- Flash Back: Loads and loads of them.
- Hannibal Lecture: Charlie gives one to T.K., and later gives one to the group as a whole.
- Hollywood Silencer: Lono has one.
- Impoverished Patrician: Avery's family "has money, but it's all on paper."
- Improvised Weapon User: Lono, in the living room, with a toaster.
- Instant Sedation: Subverted hard. It's not nearly as easy to sedate a struggling gangster as it looks on TV.
- Jerkass: Both Brett and Lono, although Lono makes motions toward being a Jerk with a Heart of Gold.
- Lima Syndrome: Big time.
- Living MacGuffin: Elise.
- The Mafia: Charlie used to run it.
- Man of Wealth and Taste: Charlie.
- The Medic: T.K.
- The Mole: Avery and Max.
- Morality Pet: Ira, for Charlie.
- No Name Given: Heckle and Jekyll. The Widowmaker.
- Noodle Incident: "So, I popped the weasel!"
- Overly Long Gag: Lono's stingray-skin boots.
- Pet the Dog: Charlie and Lono get one each. Charlie is seen in flashback rescuing a hooker from her pimp, while Lono beats up an abusive stepfather with a toaster!
- Psychopathic Manchild: Heckle.
- Retired Monster: Charlie.
- Shut UP, Hannibal: "What the [censored] are you talking about? You're taped to a chair!"
- Star-Crossed Lovers: Max and Elise.
- Those Two Bad Guys: Heckle and Jekyll.
- Throw It In: With the exception of the toaster scene, all of Denis Leary's dialog was improvised.
- Twist Ending: Avery set the kidnapping up to pay off his gambling debts, but Max and Elise went behind his back to cut a side-deal with the kidnappers.
- Urban Legends: The one Brett tells about Charlie is true. Only not quite as gruesome as what really happened.
- Villainy Discretion Shot: The camera cuts away right before Lono shoots Max and Elise. All you hear are silenced shots.
- What Happened to the Mouse?: So, whose finger did they get?
- Wicked Cultured: Charlie affects this persona, but scratch his surface and you'll find a thug underneath.