3. Danny Ocean (Ocean's 11/12/13)
Warner Bros.Clooney's effortlessly smooth heist ringleader Danny Ocean gets away with not just one, not just two, but three heists across the span of the Oceans' films. And he does it all whilst wearing a tuxedo way better than we could ever pull off. The smug git. One thing remains consistent, he is the man with the plan. Whether it's ripping off a Vegas casino, stealing a Fabergé egg or ruining a crooked businessman's casino on its grand opening night, Danny's plans are always elaborate long cons that consistently outwit both the antagonists and the audience. He's placed higher on the list than some of our other smooth con men due to his track record: he managed at least three majorly complex plots that we know of and it's inferred that he's done this before. Probably all whilst wearing that scruffy but cool tux.