As readers will learn over the course of this list, con men tend to be a little bit eccentric, some more than others. Matchstick Men's Roy Waller (Nicholas Cage), for example, is a heavily medicated obsessive compulsive - but that also makes him a very successful con man, and one that's very entertaining to watch. He loves the details and cannot function if they aren't perfect.
Over the course of the film, directed by Ridley Scott (Prometheus), Waller slowly assimilates his "daughter" Angela into his profession and introduces her to his partner Frank Mercer (Sam Rockwell). While Mercer is the flashier con man, Waller is the "brains," which makes them a perfect team. But personally, it's Cage's portrayal of the exceedingly manic Waller that makes this film so enjoyable.