Con men, or con artists, are seldom seen in feature films, not because they are hard characters to write, but because con men films are. Any great con man film requires several things: an airtight con, an intriguing “mark” or foil, and a ton of misdirection both for the characters in the film and the audience.
But most importantly, every great con man movie needs a great con man – someone who is charming, clever, cunning, and occasionally ruthless. They are typically good at heart, at least in the movies, but their goals are never noble. And make no mistake – con men are not mere thieves.
Here, in no particular order, are Our Favorite Movie Con Men.
As readers will learn over the course of this list, con men tend to be a little bit eccentric, some more than others. Matchstick Men‘s Roy Waller (Nicholas Cage), for example, is a heavily medicated obsessive compulsive – but that also makes him a very successful con man, and one that’s very entertaining to watch. He loves the details and cannot function if they aren’t perfect.
Over the course of the film, directed by Ridley Scott (Prometheus), Waller slowly assimilates his “daughter” Angela into his profession and introduces her to his partner Frank Mercer (Sam Rockwell). While Mercer is the flashier con man, Waller is the “brains,” which makes them a perfect team. But personally, it’s Cage’s portrayal of the exceedingly manic Waller that makes this film so enjoyable.
The 1988 film Dirty Rotten Scoundrels is a unique breed of con men film wherein the two leads are working against each other, not in tandem. While Freddy Benson (Steve Martin) is the boorish type, Lawrence Jamieson (Michael Caine) is the suave debonair. Both have had their successes, and both have set their eyes on one mark: Janet Colgate (Glenne Headly).
Although Dirty Rotten Scoundrels features a seemingly never-ending flurry of cons on top of cons, its juicy center is the interplay between Benson and Jamieson. Seeing Caine and Martin go toe-to-toe and play off each other is a real comedic treat, and makes the film well worth it.
Stephen (Mark Ruffalo) and Bloom (Adrien Brody) in The Brothers Bloom are the type of con artists that take the “artist” moniker to heart. They’ve spent their entire lives together – they are brothers after all – and have been conning marks practically since birth. Each has their own eccentricities (Bloom is a lover and a dreamer while Stephen loves the pageantry of a great con) and those quirks help make them a great team. And of course, it all wouldn’t be possible without their mute partner Bang Bang (Pacific Rim‘s Rinko Kikuchi).
However, what makes The Brothers Bloom unique as a film is its multi-layered approach to the central con. Good con men movies always center on a truly clever con, but great movies take things to another level by conning the audience. The Brothers Bloom pulls off such a feat and it does it with gusto.
Six Degrees of Separation‘s Paul (Will Smith) is the type of con man that doesn’t pull off elaborate heists or create intricate facades, he simply ingratiates himself to kind strangers and they, in turn, take care of him. Well, there’s a fair bit of lying involved, including mention of Sidney Poitier, but that’s typically the con man’s M.O.
Paul’s con strikes a chord because it seems the most true to life. His ability to slip so easily into the lives of the Kittredge family rings true, and Smith nails his leading feature film role. Obviously, Paul is a charmer, but this is a case where the con man is meant to be likable but not liked.
Many of the con men on our list are already pre-formed by the time the film begins, but Catch Me If You Can follows one con boy/man from first con to last. Frank Abagnale Jr. (Leonardo DiCaprio) starts out as an idyllic teenager who wants nothing more than to see his parents happy. However, as things start to unravel at home, Abagnale turns to small (we use that term loosely) cons as a form of escape. Those small cons soon turn into elaborate second lives, and before long Abagnale is on the FBI’s most wanted list.
But what truly makes Frank Abagnale Jr. one of our favorite con men is that such a man did exist, and he really did go on to work for the FBI. Granted, not all of the events in the film are true to life, but that shouldn’t undercut either the fictional or the real Frank Abagnale Jr.
Sure, there were dozens of con men films before it and even more after, but The Sting is the quintessential example. It has nearly all of the elements featured in a great con film, from the mismatched pairs to the long drawn con to the last-second double con, and all work together so well. But of course, The Sting wouldn’t be what it is without the characters of Henry Gondorff (Paul Newman) and Johnny Hooker (Robert Redford).
Yes, their characters’ names are Gondorff and Hooker but it’s really Redford and Newman on screen. It’s Butch and Sundance reunited! But, in all seriousness, both actors are pitch perfect in the roles and their con is so fun to watch play out that it’s no surprise the film won 7 Academy Awards.
David O. Russell’s American Hustle features a partially true story of another common con men trope: con artists working for the government. It’s a star-studded affair, an awards show contender, and with a little time maybe we’ll look back at Christian Bale’s Irving Rosenfeld as another classic con man.
Either way, the con men movie genre has some real standout characters already, who bolster some tremendous films with varied approaches. As has been mentioned before, a good con man cons the mark but a great con man cons the audience.
Now it’s your turn to sound off: Who are some of your favorite movie con men? Let us know in the comments below.
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