Classic Con Man Movies

Are these the top five con man movies of all time?

There was a time when con men had to rely on their cunning and wits to get by. Now, all they need is a computer and a Nigerian e-mail address. However, we can count on Hollywood to remind us of the good old days of conning. These grifters and small-time hoods have been the focus of countless movies. No tricks, no illusions, just great viewing.

The Sting (1973)

When a con man’s partner is murdered, he seeks justice the only way he knows how -- no, not through our efficient and effective legal system; he cons the murderer. He teams up with a fellow confidence man and sets up an elaborate, complicated “long con;” one that involves a cast of dozens, rigged horse races and rogue cops. It would have probably been a lot easier to just hunt the guy down and kill him. But a movie based on that violent outcome probably wouldn’t have gathered seven Oscars like this one did.

The Grifters (1990)

If your father has any type of business he is likely to wind up adding an “& Sons” to his business to carry on the tradition. But what happens when your folks are into conning? As this Oscar-nominated classic shows the scamming apple never falls far from the fraudulent tree. John Cusack plays a small-time crook who finds himself torn between his con-woman mother and his new con girlfriend. Surrounded by scheming women and fraudsters, what could possibly go wrong?

Catch Me If You Can (2002)

With Steven Spielberg behind the camera and Tom Hanks and Leonardo DiCaprio in front of it, expectations for this con movie were high. Did you really think these guys would let us down? Even under the weight of crushing expectations, the all-star cast and crew produced a slick, perfectly paced and wildly entertaining tale of an expert counterfeiter and the FBI agent obsessed with catching him. Like any con movie worth its weight, this one features twists, turns and imaginative scams. People seemed randomly hesitant to like it when it first came out, but it’s since taken its rightful place among the best of the best.

Dirty Rotten Scoundrels (1988)

Steve Martin and Michael Caine are competing con men working in a small Mediterranean village. Since they both prey on vulnerable and wealthy older women, they soon agree the picturesque town isn’t big enough for both of them and agree to a bet; the first to scam $50,000 from a beautiful young heiress gets to stay. Frank Oz, who is known most for his work on the Muppets, directed this outrageously hilarious movie. It brims with unforgettable quotable lines.

Matchstick Men (2003)

As if organizing a big swindle and suffering from OCD isn’t enough, the con man at the center of this classic con movie also has to deal with the sudden arrival of his long-lost daughter. To make things even more complicated, the poor guy’s kid takes a real liking to his chosen profession. Ridley Scott slows things down a bit from his usual fare (Alien, Gladiator) and produces a slow, methodical and mesmerizing tale of family, loyalty and honour. Not words you would usually expect to be associated with a movie about con men, but this is certainly not your average con-man movie.