2. The Joker (The Dark Knight)
Warner Bros. PicturesThere was no way he wasn't getting on this list. The master of improvisation (and really, a lot of it had to be, right?) the Joker gets higher on the list than some of the others, despite being caught, because he wins. He beats the goddamn Batman. "But Batman catches him at the end!" we hear you cry, but think about it: as he's dangling there, seemingly caught by Bats he confesses his true aim: to bring one of Gotham's mighty trinity low. At the time, he's talking about Dent, the maddened district attorney having already gone full on Two Face and murdered a hat-load of people But even when Batman rushes off to save Gordon's family from the newly created Two Face's vengeful streak, he ends up having to shoulder the responsibility of Dent's murder himself. The Joker still wins. Aside from that, his constant scheming (despite his insistence that he isn't a schemer) and over-the-top plots to cause havoc in Gotham are essentially the bulk of the movie. Hell, he basically invented this new cinematic trend of allowing yourself to get caught as all part of your big plan to screw everyone over (see Loki in The Avengers and Raoul Silva in Skyfall). "Do I look like a guy with a plan?" Well no, you don't, but there's no way you pulled all this off without an insane amount of forethought.