Additionally, commissions are typically set up in advance of a convention. Or, if they are done at the con itself, it's for pick-up the next day. This often requires some serious thought and consideration on the part of the purchaser, and can inadvertently disuade them. But a caricature, particuarly with the lower price, can be over and done before the person has a chance to second-guess themself. Obviously, the speed will be variable based on the artist, but the ones I've seen this year are frequently in the five-to-ten minute range.
The next advantage is that the person only needs to like your style of illustration. They don't necessarily need to be interested in your storytelling abilities, or the genre you typically work in. You don't have to convince them of your compatibility with their own style beyond a single piece of art.
(By the way, that photo is a picture of Greg Cravens sketching away at the Memphis Comic Expo about a week ago. I should note, though, that I've seen caricatures happening not just at the more pop culture oriented shows, but even more artsy, independent ones like CAKE.)
Advantage the fourth (I think we're up to four) is that you've got a deeper interaction and engagement with the person, making for a more memorable experience. Somebody buying a book or print doesn't need to speak to you much beyond whatever's needed for the actual transaction. With a caricature, you've got some discussion points almost built in. "What do you want me to draw you doing?" And since you're forced into more engagement and the individual has to sit/stand near your table for a while, you can use that time make a good impression with them. Instead of being another face staring blankly from behind a table like every other artist, you've become an indivdiual who's involved in some level of discussion. You're an artist that they're now making a connection with. Even if they don't buy anything else from you, they've had a positive experience and can send their friends your way.
But speaking of buying other stuff from you, you've got them stuck at your table for 10-15 minutes. You should engage in some discussion while you're drawing just to keep things from getting strangely awkward, but why not drop a few hints about whatever you're selling? I wouldn't suggest a hard sell approach, but maybe, "I've been drawing my whole life, and started this comic that I'm selling a few years ago, before it occurred to me that I could meet more people by doing caricatures." Or as you learn about the person's interests, you can drop how you have a character with a similar one.
Now, there are a couple potential downsides as I see it. While you're actually doing these drawings, you've essentially removed yourself from selling anything at your table to anyone else. Not really a problem if you've got a partner or someone who can just help man your table, but there's the potential to actually lose sales if you're not actively selling to passers-by. And of course, the whole idea is predicated on the basic concept that you have the ability to do relatively quick caricatures. If you're a writer or more of an illustrator than cartoonist, this whole thing probably won't do you much good.
But, for those who can, I think it's a great idea and I, for one, would love to see more artists at conventions doing this type of thing!
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