List by-Jarrett Leahy

One of the most fascinating and entertaining subject matter in Hollywood has always been the cunning and deviant con-artist. While disdained in real life, the con-artist on screen is an anti-hero that plays on our inner desire to outsmart and outmaneuver, and if The Man is on the other end of those smooth moves, even better. Here are six of the most clever and charming Con-Artist films that never fail to entertain…

6. The Lady Eve (1941) Barbara Stanwyck and Charles Coburn team up in this classic Preston Sturges romantic comedy to try to fleece the future fortune of a brewery heir deftly portrayed by legendary leading man, Henry Fonda. Unfortunately, neither anticipate that Stanwyck will fall for the big lug. If anyone needs convincing in Fonda’s talents in physical comedy, The Lady Eve is the perfect place to start. In the presence of Stanwyck’s Jean, Fonda’s Charles is a stumbling, bumbling klutz who just can’t stop making us laugh.
5. Catch Me If You Can (2002) Spielberg, Hanks, and DiCaprio team up to tell this unbelievably implausible yet true story of this country’s most gifted con-man, Frank Abagnale Jr., who successfully managed to convince others he was a Pan Am pilot, a medically trained doctor, and a skilled lawyer, all before the age of twenty. He also defrauded banks around the world of millions of dollars thanks to his uncanny ability in forging and altering checks. This film is so skillfully created, that some take its impressiveness for granted. While Titanic was his mega breakout role, it is Catch Me If You Can that convinced me that DiCaprio was truly going to be an acting force to be reckoned with for years to come.
4. Trouble In Paradise (1932) The perfect example of that famed Lubitsch touch, Trouble In Paradise is one of the best films of the 1930s. Miriam Hopkins and Herbert Marshall team up to form a wickedly amusing con partnership with the unsuspecting widowed heiress, played by Kay Francis, in their crosshairs. Unfortunately for them, Francis has her own form of enchanting charisma that may threaten their grand plans. Filled with innuendo and tongue-in-cheek humor that had production code officials up in arms only a few years later, Trouble In Paradise is easily as funny today as it was 80+ years ago.
3. The Sting (1973) A period piece that harkens back to classic 1930s Chicago, what more can be said about the Best Picture winner of 1973? On a scale of 1-10, Paul Newman and Robert Redford turned the charm up to an 11 as they pull the ultimate con on the man who had one of their beloved friends and partners killed. 
2. American Hustle (2013) Last year’s latest addition to the con collection is a film that surprisingly it seems you either love or hate. As you can tell, I hated so much I put it at my #2 spot 😉 American Hustle offers a 70s infused, multilayered con that exhibit some the best performances from this talented cast. It has been a true pleasure to witness director David O. Russell find his cinematic voice. If you didn’t dig the vibe of American Hustle the first time, think about giving it another chance, because for me, every viewing has been more and more damn entertaining.
1. Paper Moon (1973) What a year for con-artist films. With the undying love of The Sting, I’m sure there are quite a few out there that may question my choice of Paper Moon, but Peter Bogdanovich’s black & white masterwork is just too darn entertaining thanks in large part to the impeccable chemistry of the father/daughter duo of Ryan and Tatum O’Neal. Tatum was so good in fact that she was awarded, and rightfully so, the Best Supporting Actress Academy Award at age 10, the youngest winner ever in a competitive category. If you haven’t seen Paper Moon, it’s most definitely worth the effort to track down, if just to be reminded how gifted a filmmaker Bogdanovich was.-JL

(It pained me to have to leave Matchstick Men off this list, it is a skillfully crafted con-artist film from director Ridley Scott that offers one of Nic Cage’s best performances, and that’s coming from someone who doesn’t particularly care much for Nic Cage’s skills as an actor, so I thought I’d just add this little footnote in case you stumble across it, it’s definitely worth checking out)