Top 10 Con Men Films
By Aaron and Bob 9/26/2008
Among the bajillion movies coming out this weekend is Choke, the movie adaptation of Chuck Palahniuk’s novel of the same name. It looks over-the-top entertaining in a way that Palahniuk was just beginning to get to in Fight Club and stars the hilarious Sam Rockwell who plays a guy who fakes choking to death to get strangers to pay for his rich lifestyle. When I remembered that Sam Rockwell had been a con-men before, I realized I had to break down the top ten con men films.
10) Wedding Crashers (2005)
Surprisingly, one of the best con-artist movies is this frat pack comedy that features Vince Vaughn and Owen Wilson as guys that crash weddings. Their cons don't really take much away from their victims but they always have a back story and they are always on their game. The rules to crashing keep them from getting caught, until they are hilariously outed midway through the film. One of my favorite comedies of all time is also one of the best films about con-men. -RCK

9) The Italian Job (2003)
For all of you who think the original is great – you’re incompetent – the car chase wasn’t even that great – doesn’t even come close to Ronin. More on topic, Wahlberg and crew band together to avenge their mentor by conning Ed Norton – with a sweet cast that almost gives Danny Ocean a run for his money – the movie is solid. There’s action, humor, and lots of cons. -AWV
8) Charade (1963)
Despite the fact that this film was a straight up star vehicle for Cary Grant and Audrey Hepburn, it was also a highly entertaining romantic suspense comedy where the viewer never really knew what to expect. While the audience doesn't really know the identity of Cary Grant's character until the conclusion of the film, he certainly acts as a con man throughout, and the hidden location of the money would have thoroughly surprised me, had I not first seen the abysmal remake: The Truth About Charlie. -RCK
7) Some Like It Hot (1959)
This classic film by the great Billy Wilder features Jack Lemmon and Tony Curtis as two musicians who disguise themselves as women after they witness a murder. Hilarity ensues as the two become infatuated with Marilyn Monroe and find men infatuated with them. As a comedy on this list Wilder shows the humor that can come about from misperception and hidden identities. -RCK
6) The Grifters
Back when Annette Benning was hot, Anjelica Huston was still a name, and John Cusack was rocking the teen movies, the three of them made a seminal con man flick that was mostly about con women. Caught between a girlfriend that would make Gym Class Heroes cringe and a mother we thankfully never had, Cusack manages to pull off some pretty good small cons. But it gets interesting when they band together for the big con…-AWV
5) Matchstick Men (2003)
Matchstick Men reminded us that amid The Ant Bully and Next, Nic Cage can turn in some good acting performances. A great story, cool plot, and great supporting acting – including the aforementioned Sam Rockwell role, make Matchstick Men a great con film. Oh yeah, and Allison Lohman is really cute in it too. -AWV
4) The Usual Suspects (1995)
Pretty tough to try to make a movie better than this – but luckily Brian Singer made Superman Returns. The con in this movie is so profound that it could only be pulled off by one of the most unique actors of our generation, but hey, he also pulled off “I’m an alien,” pretty well too. Who is Keyser Soze became a cult phenomenon and Gabriel Byrne managed to fade into the woodwork. -AWV
3) Catch Me if You Can (2002)
You take a true story, you put Spielberg at the helm with Leo, Hanks, Walken and Amy Adams, well, Amy Adams wasn’t really big then (is she big now?) but that’s a great start. Following the true exploits of Frank Abignale Jr., Leo turned in a performance that made me think he could do more than fog up mirrors with Kate. Humor, suspense, character, make this a con film that rises above the rest, “do you concur?” -AWV
2) Ocean's 11 (2001)
The modern caper film that defined the smooth, cool criminal, this remake brought together a wide array of Hollywood stars who perfectly execute a Las Vegas heist. These are the high class criminals that wear tuxedos during the job and teach celebrities poker in their free time. George Clooney and Brad Pitt play a modern day Newman and Redford (see below) and assemble a team for the ages as Stephen Soderbergh brings a style to the film that is only rivaled by our #1 film. -RCK

1) The Sting (1973)
Probably the best story ever put to film about conmen, this George Roy Hill (Butch Cassidy and the Sundance Kid) picture featured the long awaited reunion of Paul Newman and Robert Redford as a pair of conmen who plan and execute a con against a Chicago crime boss as revenge. This is solid all across the board. The film is notable not only because of the aforementioned reunion of the two stars, but also because of the setting and style of the film. Set in the 1930s, the film expertly utilizes Scott Joplin music, and title cards to give a timeless feel of a time period long past. -RCK

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