And yes, No. 1 is a surprise

The 5 greatest con man (and woman) movies of all time

Last week, we provided the five best gambling movies of all time. We put together a specific set of criteria. This week we delve into con movies. While there is overlap with gambling and other genres, these are movies specifically based on con men (or women) or one big con. A movie like Trading Places has con elements, but it is not the key driving point of the plot. It is a comedy that leads to a con. Movies like that, while great, do not make our list. That would include Wall Street as well as Wolf of Wall Street. So with that specific criteria in mind, here are the top 5:

5) Oceans 11 (2001)

The original was pretty good, but the George Clooney/Brad Pitt remake is solid gold. While it could technically be considered a heist movie, the entire heist is set up by a long set of cons that creates the final plot. The acting is terrific, the story moves fast, and it features some really clever cons along the way, all designed to rip off Andy Garcia's character.

4) Catch Me If You Can (2002) 

Based on a true story, the real gift of this movie is the acting and exchanges between Tom Hanks and Leo DiCaprio, who plays a young check/forger con man who is incredibly brilliant and fills several fake roles, including doctor and airline pilot. DiCaprio is believable, clever, and constantly stays one step ahead of Hanks. A very enjoyable film.

3) Grifters (1990)

An absolute gem featuring John Cusack and Annette Benning, Cusack is a small-time grifter who winds up embroiled between Benning, his love interest, and his grifter mother, Anjelica Houston. He is talented but flawed, and those flaws wind up biting him in the end. If you watch the scene where Benning is naked and tells her landlord "the money or the lady" and aren't, um, moved, well you don't like nudity.

2) The Sting (1973) 

An all-time classic with Paul Newman and Robert Redford, this has been the gold standard for a long time. The acting is off the charts, and the twists and turns along the way make for a roller coaster ride. The original con movie won seven Oscars, including best picture, and still holds up today. It is too easy to make it No. 1 on the list. However...

1) Diggstown (1992)

Some might consider it blasphemy to put anything over The Sting, but if you have ever seen it, you will understand why. James Woods, Louis Gossett, Jr. and Oliver Platt set up a long con that involves boxing. (Because of that, some have tried to classify it as a sports movie, but it really is about the con). Pay attention to what happens early in the movie, because it sets up a dynamic finish. A young Heather Graham only adds to a terrific storyline, and vintage Bruce Dern as the mark - and a con man in his own right who tries to outdo Woods at every turn - is well worth your time. A terrific, fun movie you can watch time and time again.

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