To research this so far, I've read several books on cons and con artists, specifically things like How to Cheat at Everything, The Con Artist's Handbook, Catch Me if You Can, and Other People's Money (an autobiography of Elliot Castro).
What I'm looking for is books or films with similar characters or people, just so I can kind of see how they speak, and how they work - analyse what makes them so charming.
Bit more context; my hustler, Leo Harker, is a drama queen. He had an idyllic childhood in Newfoundland, and has never quite forgiven his parents for it. In his head, he's a hustler, someone who grew up on the mean streets of New York or Chicago or LA. He wears fingerless gloves and trilbies, and only shaves every other day. He smokes for the effect. In other words, he's a con artist, not for the money, but because it fits the image he has of himself in his head. He's aged somewhere between twenty and thirty. The main bit of the story, and most of his work, will be set in the nineties, simply because I can't keep up with new security measures. He's pretty good at poker, and can cheat well and subtley enough to give him an edge. He probably has a photographic memory (something that Frank Abagnale and Elliot Castro shared, iirc), and, as I said, he's charming. He's got a bad habit of quoting films, or of saying nonsenical things that sound vaguely cool. He has a girlfriend whom he loves, although he never really shows it - he doesn't pay attention to subtle things, assuming that if people want him to know, then they'll just tell him (although, thinking about it, how can he be a con artist and not pay attention to people? Perhaps, in his head, he draws a line between marks and friends, and doesn't analyse the latter like the former). He gets himself killed - and this is another bit I'm having some trouble with - by doing something incredibly dramatic, but also stupid. At the minute, I'm thinking he tries an old fashioned jewellery store heist, and gets shot by a new, young, nervous cop, when he moves a bit too quickly, and this policeman, who's scared out of his wits, shoots him instinctively. After his death, his girlfriend (who had an abusive childhood, and feels that he was the only person who ever truly loved her) shoots everyone involved that she can get her hands on, before being rapidly caught, commiting suicide in jail, and meeting him in limbo. There, she cannot ascend to heaven, since she can't quite forgive herself or other people for everything that happened in her life. He stays with it, and, presumably, descends to hell. I'm thinking there was a bit of selfishness there, too - after all, Charlie Barkin, another character who Leo admires and resembles, refused heaven for being too predictable and safe.
So, yeah, forgive the rambling. I'm trying to pin the character down in my head, and that's one aspect I'm having a lot of trouble with. Any ideas? A few characters I've come across so far who I've used for inspiration are Charlie Barkin, of All Dogs Go to Heaven, and JD of Heathers. And a little bit of Frank Abagnale.
One last request - can anyone think of any scenes, in books or films, that show a loving, supportive relationship? I'm thinking of that bit in Road to El Dorado, when they still manage to act in unison and hit the guy watching, even while they're really angry at each other, and trying to hurt one another. Or like Jim and Silver's relationship in Treasure Island - some vision of love other than the cliched ones, that's based on something more than just being soul mates, or eyes meeting across a crowded room.