I've been studying the art of caricature lately and reading through Tom Richmond's fantastic book, The Mad Art of Caricature. It's fascinating, not because it's hard to do (which it is), but because it's so hard to do WELL. I see a lot of people whose artistry is fantastic, but the caricature itself is lacking. They seem to think that a good caricature is basically what you would get if you put a photograph of a person under a thin layer of rippling water. Either that, or just make them look really freaky and distorted. That's not the point. A good caricature plays off of the way that the brain naturally works - focusing on certain distinctive features of a person that differentiates them from every other person, and emphasizing it. I feel like I've been getting better, but it's taking a lot of work. I want to get to the point where I feel comfortable doing live caricatures, but man, that's a lot of pressure. The only way to get there is through a lot of practice! (and Tom's book helps a lot too).