This 1990 neo-noir crime drama is an adaptation of the pulp novel by Jim Thompson. It earned Academy Award nominations for Best Director (Stephen Frears), Best Actress (Anjelica Huston), Best Supporting Actress (Annette Bening), and Best Adapted Screenplay (Donald Westlake). Bening was also nominated for a BAFTA, while Huston was nominated for a Golden Globe.
When con artist Roy Dillon (John Cusack) is visited by his mother Lilly (Huston), who is also a con artist, she sends Roy off to the hospital because of a blow to the gut he suffered while working a grift. Roy's girlfriend, Myra Langtry (Bening), the third con artist, comes to visit Roy, and we discover that Lilly and Myra don't get along. After he is released from the hospital, Roy and Myra go on a little trip, where he is propositioned to be partners in crime with Myra. Everything soon falls apart for the three con artists, which leads to a bloody climax.
The film provides examples of:
- Accidental Murder: Lilly tries to knock Roy out by hitting him with a suitcase but accidentally causes a glass of water Roy was holding to shatter and stab him in the throat. He dies moments later and Lilly is horrified at what she's done.
- Ate His Gun: The police assume this was how Lilly committed suicide. In reality, Lilly is very much alive and it's actually Myra who died this way when Lilly shot her in the face.
- Awesome Mc Coolname: Bobo Justus is a fantastic name for a Mafia crime boss.
- Batman Gambit: The long cons that Myra and Cole used to work.
- Blatant Lies: When Roy asks Myra what happened to Cole, she claims he retired to Atascadero. Then we see the end of the flashback showing Cole has gone insane to the point he's afraid of getting off of his bed. Roy knows the city has a hospital for the criminally insane, but Myra continues to insist Cole's "retired".
- Chekhov's Gun: The cigar burn on Lilly's right hand.
- The hotel clerk mistaking Myra for Lilly because they look alike.
- Cigar Chomper: Bobo. He even uses one as an implement of torture.
- The Con
- Cool Shades: As seen in the poster and the opening of the movie, all three main characters wear sunglasses to conceal themselves public and to look cool.
- Crapsack World: It's pretty bleak. Everyone is out to get each other and there is literally no one who can be trusted.
- Dramatic Stutter: A beating with a bag of oranges can cause "p-p-permanent damage".
- Dumb Blonde: Myra acts the part but it's part of her con.
- Faking the Dead: Myra and her former partner Cole used to end their scams by staging a shooting in which Myra would always "die". It guaranteed that their targets never went to the police.
- On a larger scale, Lilly fakes her own death after shooting Myra in self defense. She assumes Myra's identity to throw Bobo and his hired killers off her trail. It doesn't take long for Roy to figure out the truth.
- The ending has been interpreted as suggesting that Roy did this. This interpretation wasn't intended by the filmmakers, but has gained popularity.
- The Film of the Book: John Cusack had read the book previously, had wanted to make it into a film, and jumped at the chance offered by Scorsese.
- Fixing the Game: Lilly's job is to skew the odds at the race track on behalf of an out-of-town bookie by betting on long-shots to alter the payout.
- Hollywood Silencer: Lilly's gun barely makes a sound because of this.
- Hustling the Mark: Roy does this to a group of sailors on a train. He pretends to have found dice on the ground and cons them into gambling with him.
- Identifying the Body: After Lilly Dillon and Myra Langtry have their fight-to-the-death, Roy Dillon is called in to identify his mother's body. He notices that her hand doesn't have the scar that it should, and realizes that it isn't her body - it's Myra's. He identifies it as Lilly's anyway, because he realizes that she's on the run and needs people to think she's dead.
- Ms. Fanservice: Myra certainly likes to take her clothes off.
- My God, What Have I Done?: Lilly has a moment like this after accidentally killing Roy in her desperation to get his money. Though it doesn't stop her from stashing the bloodied bills and making a getaway in Roy's car.
- Offing the Offspring: Shocker of an ending.
- Opening Monologue:Narrator: Around the country the bookies pay off winners at track odds. It's dangerous when a long shot comes in. Unless you have somebody at the track to lower those odds.
- Parental Incest: Implied until the end.
Lilly: What if I wasn't your mother?
- Parents and children typically don't have sexual feelings for each other because of all the time spent growing up together. Lilly had Roy when she was fourteen or fifteen and gave him up for adoption. Does she see Roy as her son, or as a handsome young man? Does he see her as his mother, or as a good-looking, not-that-much-older woman?
- Pillow Pistol: Lilly Dillon does this.
- Pragmatic Villainy: Bobo prefers that his employees skim a certain amount for themselves, under the assumption that someone who isn't stealing a little bit is probably planning to steal a lot.
- Quick Change: One of Roy's favorite tricks. To confuse a cashier, he held up a $20 bill but actually paid with a $10 bill. Unfortunately the second guy he tries this on is wise to the trick, and inflicts serious damage by hitting Roy in the stomach.
- Short Con: Roy specializes in quick, one-off tricks that involve little risk. Myra tries to convince him to work a long con with her.
- Shout-Out: The final shot is a direct visual reference to The Maltese Falcon.
- Sock It to Them: There's a discussion on the pain and damage that can be inflicted with a sack filled with oranges.
- Trickster Mentor: Roy Dillon finds a Con Man and asks to be taught how to be a grifter. The man agrees and gives him some advice. At the end of their conversation the man asks Dillon for $20. After Dillon gives it to him, the man says "Come around tomorrow, I'll take you again."
- Would Hit a Girl: Bobo to Lilly during the oranges sequence.
- Wrote the Book:Lilly Dillon: You're working some angle, and don't tell me you're not because I wrote the book!