Five of the Greatest Con Artist Twists of All Time

Stop. This post is spoiler filled. And they are spoilers of some of the greatest, most enjoyable mindjob movies ever filmed. Is there a more mindjob-esque movie than a con artist movie? One of the true joys of living is going into a con movie, knowing that a con is going to happen, only to be surprised. Trust me, there can be no more difficult screenplay to dream up than that. So, all that to say, I will give you the list of the movies I will cover below. Make certain you’ve seen them all before you march further down this page. I will also give you links in order to watch them there where you sit. Then! Then you can come back and read through the list of feints and clever twists that sit atop the pile. OK?

#5 – Catch Me If You Can – The Airport Walk

Featuring Tom Hanks and Leonardo DiCaprio (revenant much?), Catch Me If You Can is a fast-paced and hugely entertaining film based on the real-life cons of Frank Abagnale Jr., who stole millions of dollars by posing as, among other things, a Pan American World Airways pilot.

In one of the more memorable sequences in the film, Frank (DiCaprio) realizes that the FBI, headed up by Carl Hanratty (Hanks) stakes out an airport in which he pretends to be a Pan Am pilot. To escape, he surrounds himself with glamorous Pan Am flight attendants, using the distraction they provide to slip away from the agents sent to arrest him. This social engineering maneuver shows all the traits of intelligence, wit, confidence and distraction that make conmen such great entertainment on the silver screen.

#4 – Ocean’s Eleven – The SWAT Team

Although I am not an enormous Ocean’s Eleven fan, this one is obvious, and has to be included. Eleven is the movie that had such a good grift, and inside out execution, that it has successfully sailed three movies in its likeness. Eleven is undoubtedly one of the best-known heist movies (Second only to The Sting), mostly because of the almost improbable amount of star power stretched over both the original and the sequels. The heist part of the movie is a series of con jobs used to separate a suitably villainous Andy Garcia from his money. The reveal, and the scene that stands out the most in Ocean’s Eleven? Well, it would be Clooney and Co. removing their SWAT gear, driving away with piles of cash. No other big budget grifter flick has pulled off a reveal like this one in modern times.

#3 – The Grifters – The Body Swap

Roy (played by John Cusack) has a bit of an Oedipus problem with his mother Lilly. So much so, for years now, I have considered doing a post just about The Grifters that would liken Roy and Lilly to the Greek Tragedy Oedipus Rex. But today is not that day. But I do believe The Grifters has one of the greatest con moments ever.

Roy’s (played by Cusack) girlfriend Myra (played by Annette Bening) attempts to murder Roy’s mother Lilly (played by Anjelica Huston). Why, because Lilly has been stealing from Bobo. Got it. Simple enough. But when Roy is called into the Phoenix police to identify his mother’s body, things go oddly pear shaped. Lilly’s body, shot in the face, is difficult to identify. And while identifying it, Roy even mentions the lack of the cigar burn on her hand. Then, upon returning home, he finds Lilly attempting to steal all of his money. And that is when we find out that she actually passed Myra’s body off as her own after accidentally shooting her in self defense.

#2 – Nueve Reinas – Conning the con man out of $200,000

Nueve Reinas is my favorite Grifter movie of all time. And to land at my number one, you better have a very compelling twist. The movie opens with a brilliant conman Marcos, into thinking he’s helping a fledgling con artist avoid the police. Which then sordidly bends and weaves until Marcos puts up $200,000 as they bait Juan into contributing $50,000. Which, Juan does not want to do. A bank crash and a fleeing mark later, Marcos believes he is about to be ruined. And as the curtain drops, we realize that Marcos’ $200,000 was the mark all along.

#1 – The Sting (1973) – Playing Four Jacks

The Sting is literally the beginning of a genre. Like Rocky, The Sting created it’s own section at Blockbuster. (Kids, a Blockbuster was a place where your parents went to rent a movie before Netflix.) And it starred the inimitable duo of Paul Newman and Robert Redford no less. It’s a roller coaster of a movie, with more twists and turns than that penny horsey ride at your local grocery store. It rightly won seven Oscars, including Best Picture, Best Director and Best Original Screenplay. Enough heralding. You know the movie.

Early in the film, Henry Gondorff (Newman) and Johnny Hooker (Redford) look to take down crime boss Doyle Lonnegan, played by a hugely threatening Robert Shaw. Shaw has cheated at a local high-rollers poker game, and the pair decided to turn the tables on him. The right hook curve ball was delivered home by Newman’s acting like the drunken and loud idiot. And it’s Lonnegan’s own “cold decking” that really sells this switch, as it enraged Lonnegan when he realizes he’s been had. After all, as Lonnegan himself says: “What was I supposed to do? Call him for cheating better than me in front of the others?”

Edited by: CY