Okay, so maybe it's more than 10 films, but that will teach you not to believe everything you read.
The Sting (1973)
Still one of the greatest movies ever made about the long con. Stars Paul Newman, Robert Redford and Robert Shaw who later went on to play Quint in "Jaws" (nails on a blackboard, anyone?). Directed by the great George Roy Hill, who first teamed Newman and Redford in a little gem called "Butch Cassidy and the Sundance Kid."
Paper Moon (1973)
Directed by the also great Peter Bogdanovich, starring Ryan O'Neal and his daughter Tatum, who at 10 won the Oscar for Best Actress and was the youngest to win a competitive Academy Award. Adapted from a novel, "Addie Pray," it tells the tale of a young girl left on a small-time short con operator's doorstep. The two grift across the country, intent on returning Addie to a distant relative, but Addie has other ideas.
The Hustler (1961)
Black and white and totally awesome, this movie is an ode to pool hustling. Paul Newman is a great pool player, but he's a hot head and, according to the character portrayed by George C. Scott, a loser. Newman has a chance to prove himself by beating the best, Minnesota Fats, played to perfection by Jackie Gleeson. Piper Laurie is Newman's alcoholic girlfriend who ends up as collateral damage in the heartless world of gamblers and hoodlums. Talk about swimming with sharks.
The Color of Money (1986)
A sequel to "The Hustler," 25 years later, Newman reprises (gosh, it's fun to say "reprises") his role as pool shark Fast Eddie Felson, teaching a raw young talent (Tom Cruise) the ways of the hustle. Directed by Martin Scorsese, this movie travels the back pool rooms of the country, ending in a giant tournament where money isn't the only thing on the line.
The Grifters (1990)
John Cusack, Angelica Huston and Annette Benning – not a bad starting line up for anything, except maybe a competitive softball team. This wonderfully twisted story of a crooked mom's creepy relationship with her crooked son and his relationship with a crooked girlfriend shows many classic grifts along the way. But when small-time thieves get in trouble with the big boys, someone's gonna get hurt.
Oceans Eleven (2001)
George Clooney and Brad Pitt would be enough for any movie franchise, but add Matt Damon and eight other powerhouses, plus director Steven Soderbergh, and you've got a recipe for multiplex gold. It's a loose remake of the 1960 version staring the Rat Pack (you know who they are). In the current version, a bunch of long con operators want to rob the vault of three Vegas casinos in one night and, lest the title mislead anyone, they need 11 guys to pull it off.
Catch Me If You Can (2002)
Steven Spielberg cast Tom Hanks and Leonard DiCaprio (because he's Spielberg and he can just pick-up the phone) to tell the true story of Frank Abagnale, Jr., a man who kited more bad paper than Benjamin Franklin. Abagnale became such an expert at forgery and its tricks that he ultimately became an advisor to the FBI. The graphics in the opening credits are particularly fun.
Matchstick Men (2003)
Ridley Scott directed Nicolas Cage as a con man suffering from OCD, whose partner, Sam Rockwell, like all con men, is not to be trusted. When a young girl enters Cage's life, he – like Ryan O'Neal in "Paper Moon"– reluctantly teaches her the ways of the grift, only to be taught a lesson or two himself in the process.
House of Games (1987) and The Spanish Prisoner (1997)
Two by David Mamet. "House of Games" is better, but if you're studying to be a con man, both are required viewing. The plot for both is basically the same – nothing you see is real, or is it? Everything everyone says is true – or is it? No one is who they claim to be – or are they? You get the idea. If you like guessing who's zoomin' who, these are both good.
Dirty Rotten Scoundrels (1988), Leap of Faith (1992) and Sergeant Bilko (1986)
Speaking of Steve Martin (he's in the "Spanish Prisoner"), here are three fun flicks to add to the hustler library. In each, Martin plays a con man and he plays them well. Who says movies about cons have to be serious?
The Music Man (1962)
If you need a good musical (and who doesn't) check out this classic movie about Professor Harold Hill who comes to Iowa to form a band (76 trombones, anyone? Bueller?) Too bad he doesn't have any credentials, let alone uniforms or instruments. Still, it doesn't stop him from selling these items to the local yokels. When it's time to hit the road, his foot gets caught in the door with a comely librarian (there's another good word, comely) played by Shirley Jones, who would later con us into believing she's Mrs. Partridge and that the Partridges were a real family.
Lock, Stock And Two Smoking Barrels (1998)
Directed by that guy who married Madonna. Oh yeah, Guy Ritchie! This movie is more about card players, but there are some classic scam moves early in this that make it fit the list. Also, it's just a fun, stylish flick and a great predecessor to Madonna's husband's later movie, "Snatch."
The Flim-Flam Man (1967)
Haven't seen this in so long we don't remember what it's about, except George C. Scott is a Flim-Flam Man and he teaches Michael Sarrazin to do the same. Maybe not. We know they're both in it and it's about grifting, but beyond that, you're on your own. We don't have time to educate you guys all day; there are pockets to pick.