The 1990 film is an adaptation of a pulp novel by Jim Thompson. It was nominated for four Academy Awards (Director, Lead Actress, Supporting Actress, Adapted Screenplay). Annette Bening was nominated for a BAFTA, and Angelica 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.
- 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 McCoolname: Bobo Justus is a fantastic name for a Mafia crime boss.
- Batman Gambit: The long cons that Myra and Cole used to work.
- 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 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 by betting on long-shots to alter the payout.
- Hey, It's That Guy!: J.T. Walsh, in a flashback scene, plays Myra's old partner Cole Turner.
- 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.
- Incest Is Relative: There's a strong sexual subtext between Roy Dillon and his mother Lilly at the end it becomes more than subtext with disastrous consequences.
- Lady in Red: Lilly and Myra.
- Martin Scorsese: He was the producer who subsequently brought in Stephen Frears to direct while he produced.
- 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.
- One-Scene Wonder: Two of them; Pat Hingle (as Lily's boss) and J.T. Walsh (as Myra's old partner).
- Opening Narration:
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.
- Pillow Pistol: Lilly Dillon does this.
- 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.
- 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.
- 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 $10. After Dillon gives it to him, the man says "Come around tomorrow, I'll take you again."
- Wrote the Book:
Lilly Dillon: You're working some angle, and don't tell me you're not because I wrote the book!