Top 10 Coolest Criminals

10. Frank Abagnale Jr (Catch Me if You Can)

Nearly loses cool points for using aliases cribbed from comic books (Barry Allen?), but Frank not only manages to make the FBI look like a dog that caught its own tail and then go its snoot lodged in its buttcrack, he also uses crime as a way to snag hot women, which we can all understand and appreciate.

9. Lester "Worm" Murphy (Rounders)

OK, so he doesn’t have the cajones to face Teddy KGB like a man, but you have to admire a guy so calm and collected that he’ll cheat a prison full of thuggy inmates out of their cigarettes and he doesn’t even smoke. Those are large, and cucumber cold, balls indeed.

8. Harry Lockhart (Kiss Kiss Bang Bang)

The sign of a smooth criminal is being able to keep your wits about you and turn lemons into lemonade. Well, Harry turns getting shot at and running from the cops into a kick-ass audition for a movie role. That’s how you do it.

7. Unnamed (Layer Cake)

A huckster so slippery, he goes through an entire movie and no one even catches his name. He’s a man of principles and a crook who knows his limits—this role might have secured Daniel Craig the Bond role, but Layer Cake proves he’s much better on the other side of the law.

6. Terry Leather (The Bank Job)

Maybe he’s not a master criminal (he does still need a day job, after all), but Terry is a no-nonsense, blue-collar safe cracker of the highest order. No flip-outs or psychotic breakdowns here. He can take the heat and stay in the kitchen long enough to bore through the tiles and enter the bank vault next door.

5. Rusty Ryan (Ocean’s 11)

The gang might get its name from "leader" Danny Ocean, but everyone knows that Rusty is really the man running the show. And he’s doing it with a shrimp cocktail in one hand. Rusty defines "unflappable," even when staring down a preening Topher Grace.

4. Neil McCauley (Heat)

What kind of rare metal stones do you have to have dangling between your legs when you can sit down and have coffee with the cop trying to nab you and not even break a sweat? Neil isn’t greedy or crazy, just professional and precise. A model crook.

3. Jack Foley (Out of Sight)

Jack sees Neil, and raises. He doesn’t have coffee with the cop trying to nail him, he nails the cop trying to nail him. You have to be some kind of silver-tongue devil to pull that one off. Of course, to be fair, Jennifer Lopez is a lot better looking than Al Pacino.

2. Frank Lucas (American Gangster)

Lucas manages to, literally, buy and sell half of Manhattan without so much as rippling the radar of local law enforcement (until an ill-advised night out in a mink coat). That’s the kind of power you can’t get when you’re a cackling nutcase.

1. Thomas Crown (The Thomas Crown Affair)

So brazen, he practically tap-dances on cop cars with a "I Heart Art Theft" T-shirt and they still can’t even come close to nabbing him. Crown is smug, smooth, and steals only for the thrill of it. He’s the gold standard because he makes a life of crime seem like one long, uninterrupted Bacardi ad.