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Five Movies About Con Men

Heist and robbery movies are a popular genre, but the bad guys in those films always seem to be a half-step slower than con men. When you’re watching a movie about a con, there’s a nervousness and unease that maybe you’re getting played along with the marks up on the screen. That can make for a more engaging and exciting viewing experience, despite the lack of car chases and gun play.

The Sting (1973) — IMDB.com rating 8.3/10 (182088 votes)

This is the classic con man movie. Great acting, great directing, great costumes and sets, and a great script. The Sting won seven Oscars, and was a huge box office hit that’s aged well. Young hustler Johnny Hooker (Robert Redford) runs a short con that goes wrong, and seeks out wily old swindler Henry Gondorff (Paul Newman) for help. The two find themselves up against crooked cops, crime bosses, and each other.

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Everything in The Sting works, and works well. Sometimes it works so well that we forget to ask ourselves whether we can believe what we’re seeing on screen. And we forget to ask what we’re missing. So we fill in the small gaps of what we’re not seeing with our own assumptions, and it’s easy to get things wrong.

The Spanish Prisoner (1997) — IMDB.com rating 7.3/10 (18971 votes)

David Mamet has made a number of top-notch movies about scam artists (including House of Games and Glengarry Glen Ross), but The Spanish Prisoner is his best because the plot is the slickest, and we get to see the con — and the players — broken down to their purest forms.

After all, what are the essential elements of a con? A thing of value — here, an unspecified “Process” (which brings to mind the never revealed thing inside the suitcase in Pulp Fiction), the person who has possession of that valuable thing, and the person who wants to take the thing by deception.

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Joe Ross (Campbell Scott) created the Process for his employer. Joe meets Jimmy Dell (Steve Martin), who plays on his suspicions that he won’t be fairly compensated for his creation. Jimmy quickly builds trust with Joe, ultimately putting Joe in a very compromised and vulnerable position.

Whom can a person trust? Can a person even trust their own instincts? Cons work because of the most basic and automatic aspects of human nature. We like to watch con movies because we can see ourselves in both the con man and the mark.

The Grifters (1990) — IMDB.com rating 7.0/10 (21287 votes)

Movies about con artists tend to focus on the top of the food chain — the big con, the suave practitioners, high dollar scams. But The Grifters lets us see the bottom of that chain. Roy Dillon (John Cusack) runs the smallest of the small cons — a few bucks here and a few bucks there… His mother and girlfriend are also grifters, but play for higher stakes. Roy is weak, and these two women are insatiable; so when they meet they immediately begin to battle over who gets to devour him.

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These con artists are not slick or worldly. They’re perpetually desperate, and they’re not good people. Their cons aren’t particularly creative or flashy. Watching how they live, not once are we tempted to envy their existence. The Grifters is worth watching because it de-glamorizes the vocation of con man. It reminds us that con men and con women are criminals, and that even if the con artist never has to deal with law enforcement, they lead a tough and dangerous life.

Dirty Rotten Scoundrels (1988) — IMDB.com rating 7.3/10 (52194 votes)

They’re certainly no Gondorff and Hooker… but Freddy Benson (Steve Martin) and Lawrence Jamieson (Michael Caine) sure are a lot funnier. They run different types of scams on the French Riviera, each leveraging their individual strengths. Lawrence is older, distinguished and refined, while Freddy has a youthful energy that lets him play the short con.

Dirty Rotten

Freddy is forced out of town, but blackmails his way back onto the scene and demands training from the more experienced Lawrence. When that training proves to be more than enough for Freddy to bear, the two con men find themselves at an impasse. In order to decide who has to leave, and who gets to stay, they face off by going after the same mark; a vulnerable young woman who recently arrived as a tourist. The first to con her out of $50,000 will be declared the winner.

The long con plays out through a series of hilarious set pieces. Caine and Martin are an excellent team, and have great screen chemistry. The twists and turns aren’t quite as satisfying or serious as those in The Sting, as the film trades in drama for comedy across the board, but they’re still fun to watch.

Paper Moon (1973) — IMDB.com rating 8.2/10 (23991 votes)

Cons work because the scammer appeals to some particular aspect of the mark’s humanity. That’s quite often greed or vanity, but sympathy and feelings of loss can also work quite well. Playing on the target’s maternal instincts works well, too.

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Moses Pray runs a simple but effective con that plays off the vulnerable states of recently widowed women. While attending a funeral he meets Addie, a nine-year-old girl who may or may not be his daughter. He agrees to take the girl to her aunt’s home, and along the way discovers that he can up his con game by bringing the child into the mix.

Ultimately, though, Paper Moon is about a con man’s own humanity. Does he have anything left inside that isn’t jaded and corrupt? After cheating and lying to so many people, is there any honesty or vulnerability remaining in himself?

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About Me

In 1976 I went to see The Sting with my father and sister.

Unfortunately, we arrived at the theater an hour after the show started. We went in anyway, and watched the last half of the movie. After the movie was over we stayed until the next showing, so I eventually got to watch the first half of the film (already knowing how it was going to end).

I was struck by the magic of the movies, and how we could be tricked by the actors (and by our own assumptions of what's happening on the screen), and how this was a wonderful thing.