I've never robbed anyone who didn't deserve it

My favourite character archetype, giving rise to one of my favourite subgenres of literature, is the Gentleman Thief. From the medieval Robin Hood who robbed from the rich to give to the poor, to the 18th-century highwayman who robbed from the rich and... well.. that's about it really, through Arsène Lupin and Raffles, Simon Templar and Lupin III, Thomas Crown and Danny Ocean, there's something positively alluring about a guy who's taking somebody else's money and looking absolutely stylish while doing it.

It takes a special kind of thief to become a popular hero in that vein. Bonnie and Clyde nearly managed it; Dillinger almost certainly did. It's not enough to be incredibly dapper; if you're mugging people in tophat and tails, you're still just a mugger. And it's not enough to pick your targets carefully; a guy who rips off a casino that nobody liked in the first place might get the viewers at home chuckling over the apparent justice, but they won't be rooting for him and actively hoping he doesn't get caught.

The gentleman thief is an iconoclast, the man (or woman) who can take on the accepted power structure - the banks, the casinos, the fat cats and businessmen that every prol schmuck secretly or not-so-secretly envies and hates deep in his heart of hearts - and can do it successfully, with clever wit to keep from getting caught - and a large dash of bravado and daring, allowing them to turn around during their getaway chase and thumb their noses directly at the police.

The gentleman thief does not content himself with just sticking up a bank; the gentleman thief breaks into the office of the corrupt bank manager, sits down and smokes a cigarette and waits for the manager to arrive as casually as if he were there to keep a legitimate appointment, and then very politely asks the bank manager to hand over the keys to the safe. When the bank manager doesn't, of course, more drastic measures will be required, and that is where we find the derring-do that makes for a good adventure story; but the charming insouciance of asking and apparently honestly expecting it to be handed over without any trouble is what separates the gentleman thief from his coarser cousins. A robber produces a gun immediately; a gentleman thief produces it with a show of winsome reluctance, no matter how eagerly he may actually use it in the ensuing struggle.

Obviously, gentleman thieves roll very high in CHA, in addition to the high DEX skills that are required for all of their ilk.

The Decemberists - Perfect Crime #1 (website)
The Films - Black Shoes (website)
MIA - Paper Planes (website)
The Clash - Bankrobber (website)