Two shows that I thought of on the way home that you might like to check out if you want some ideas about grifters and con artists.

The first is a decent show on TNT called Leverage. The first two seasons are available on Netflix streaming if you have access to it. There aren't classic cons per se, but it has a pretty good Ocean's Eleven kind of vibe as a team of thieves set things right for those that are abused by The System. While I know you aren't going for that particular vibe, it might give you some general ideas. http://en.wikipedia.org/wiki/Leverage_(TV_series)

The second is a great show from the BBC called Hustle. It's a show about a bunch of grifters pulling tons of cons. The best part is that they run all the classic cons like the "Spanish Prisoner," the "Wire," the "Badger Game," and the "glim-dropper" (though they swap out the false eye for a diamond ring) among many many others. There are a number of seasons available through Netflix (unfortunately not through streaming). http://en.wikipedia.org/wiki/Hustle_(TV_series)

It's funny, while I was looking for the names of some of the cons in Hustle, I stumbled across this list of cons on Wikipedia that you guys might like: http://en.wikipedia.org/wiki/List_of_confidence...

You should also look at the Redemption of Althalus by David and Leigh Eddings. It's a look at an unrepentant rogue and scoundrel who has a personal relationship with his Lady and Savior, Luck, who is tapped by another goddess to save the world. He steals and swindles his whole way through.

The beginning chapters are probably the best part as they deal mostly with him being an unrepentant thief. The flavor of it is very refreshing.

Wow! You both blew my mind with the thieves approach. It takes me back to a 1st/2nd edition D&D campaign I ran in college. Running for a bunch of creative players was a challenge, especially when one of them knew everything in the Monster Manuals. Cool idea, like a fantasy _Great Train Robbery_ (the book not so much the movie).
Follow Your Bliss,
JJ

Listening to this -- you guys need to read "The Lies of Locke Lamora" by author and fellow gamer Scott Lynch. It's basically "Oceans 11" in a fantasy world -- high-level scams, etc. It's the first book of his "Gentlemen Bastards" series.

Thanks for the tip, GMS. I haven't read those, yet.