There is something about con artists that are so interesting to audiences. In reality, con artists are probably much less glamorous than what we see on film, yet watching these people make a living lying and cheating with such smoothness is intoxicating to watch and they make for compelling characters to follow.
Some of these con artist films can fall flat if we don’t believe in the characters or don’t think the elaborate schemes they pull off are very interesting. However, when done well, these movies can be the most entertaining, edge-of-your-seat fun you can have with a movie. Here are some of the greatest movie con artists.
Roy - Matchstick Men (2003)
Usually, we see movie con artists as suave and slick operators which is why Roy (Nicholas Cage) is such an interesting take on this kind of character in the underrated Ridley Scott movie, Matchstick Men. Roy is very good at swindling unsuspecting people out of money, but his personal life is chaotic due to his obsessive-compulsive disorder.
While working on an extremely lucrative and ambitious con with his protégé Frank (Sam Rockwell), Roy receives a surprise visit from his long-lost daughter which complicates things. Regardless of his flaws, it’s interesting to see how much Roy can pull himself together to pull off a job.
Irving Rosenfeld - American Hustle (2013)
Irving (Christian Bale) is another con artist who doesn’t look as debonair as what one might expect in this type of character. But he still knows how to play the game better than anyone out there. He also truly sees himself as an artist who isn’t doing anything wrong. In his mind, everyone steals, he’s just more ambitious about it.
After getting caught by the authorities, Irving is forced to cooperate with the feds on their own sting operation. And while it might seem like Irving has lost all the power, he still knows how to play even the biggest players.
Freddy And Lawrence - Dirty Rotten Scoundrels (1988)
We’ll see throughout this list that con artists seem to enjoy working in pairs. However, in the case of Freddy and Lawrence in Dirty Rotten Scoundrels, they get their fun from competing with each other to see who is the greatest grifter of them all.
Freddy (Steve Martin) is a womanizing and impulsive con while Lawrence (Michael Caine) is an upper-class smooth operator. Though they have very different approaches, they both show great talent for their games of deceit as they attempt to swindle the same rich woman.
Bloom And Stephen - The Brother’s Bloom (2008)
The Brother’s Bloom is an underrated gem that cemented Rian Johnson as a unique filmmaker in his second feature. Bloom (Adrien Brody) and Stephen (Mark Ruffalo) are brothers who combine forces to become one of the best con artist teams in the world. While some swindlers are satisfied with the quick and easy schemes, these brothers create elaborate and complex stories planned out to the very last detail.
When Bloom decides he’s had enough of the world of crime, Stephen convinces him to do one more big job. They plan to steal from an eccentric heiress (Rachel Weisz) by taking her on a globe-trotting adventure. Though the cons might be a little over-the-top, it’s clear that these guys put their hearts into their work.
Wanda - A Fish Called Wanda (1988)
Most con artist films have a beautiful woman at the center of the scheme to act as the seductress. Though it is a bit of a tired cliché, Wanda (Jamie Lee Curtis) is certainly one of the more interesting of these kinds of characters in the hilarious romp A Fish Called Wanda.
Wanda is partners with Otto and the two pull off a diamond heist together, only to be double-crossed. It’s then up to Wanda to get into the good graces of a bumbling lawyer (John Cleese) in order to retrieve the missing loot. While the men all make fools of themselves, Wanda seems to be the only one with an actual plan.
Daniel And Peachy - The Man Who Would Be King (1975)
The Man Who Would Be King is a unique con artist film as it takes that subgenre of film and transplants it into a sweeping epic adventure story. Set in the late 1800s, the story follows Daniel (Sean Connery) and Peachy (Michael Caine), two former officers in the British Army who seek fortune in the Middle East.
After a misunderstanding, the locals become convinced Daniel is a god and begin worshipping him. The two friends take full advantage of the begin living a life of luxury. While their egos get carried away with the scheme, it’s clear that these two are more interested in the adventure rather than the fortune.
Moses And Adie - Paper Moon (1973)
Paper Moon presents another conning duo and, like The Brothers Bloom, this one is a family affair with real-life father and daughter team Ryan O’Neal and Tatum O’Neal starring in the film. Moses is a conman during the Depression Era who agrees to transport a young girl named Adie across the country following her mother’s death.
As the mismatched pair make their way across the dusty and desperate country, Adie picks up on Moses’ line of work and takes an interest. Soon the two form a professional partnership as the youngster proves to be a natural at the work.
The Kim Family - Parasite (2019)
Once again, the work of con artists seems to be ideal as a family line of work. Parasite is the South Korean thriller and Best Picture nominee at this year’s Oscars that explores class differences in a bizarre and thrilling con artist story.
When the son of a lower-class family gets a job tutoring for a wealthy family, he sets in motion a scheme to get his whole family working for this affluent and gullible family. While the Kims are brilliant at infiltrating this world, they soon find themselves in a more complicated situation than they intended.
Henry And Johnny - The Sting (1973)
After proving they are one of the most dynamic onscreen duos in film history in Butch Cassidy and the Sundance Kid, Paul Newman and Robert Redford teamed again for another buddy movie with The Sting.
This time around, the iconic pair were playing con men. Redford plays Johnny, a young criminal whose partner is killed by a dangerous gangster. He then seeks help from an old pro, Henry (Paul Newman), to make the gangster pay. The two men make for a wonderful team with plenty of twists and turns that make you root for them even more.
Frank Abagnale - Catch Me If You Can (2002)
What puts Frank Abagnale from Catch Me If You Can at the top of the list is the fact that his story is true. In the film, Leonardo DiCaprio brings Frank’s story to the big screen as this young teen who runs away from home and begins forging checks to support himself.
Frank soon discovers that people in positions of power seem to get away with more and he sets out to pose as an airline pilot, a lawyer, and a doctor while cashing millions of dollars in checks. While it might seem farfetched, the true story makes it all the more thrilling.
