Drawing caricatures isn’t as easy as you might think. Oh sure, you’re saying, “Boy, I wish I could get paid 25 bucks an hour to chat with people and doodle, which is what I do when I’m bored anyway.” Okay, so that part is easy - although it doesn’t justify talking aloud to a newspaper. But coming up with innovative drawings after five hours of sketching seemingly identical grinning faces can be plenty tough.

Caricaturing as an art form tends to be taken for granted. Most people at least subconsciously acknowledge that cartoons and comic strips are done by different people with different styles, but they assume a caricaturist is going to draw a portrait in a very specific way.

This presents problems when you’re the person doing the drawing. While creating a formula for drawing — taking artistic “shortcuts” when drawing certain features — is fast and provides dependable results, it can detract from the individuality of the caricature. And it can get boring faster than you can say, “smile!”

These shortcuts occur as my mind starts to generalize and group features of my subjects together. For instance, all babies look pretty much the same. They all have the same eyes, petite nose, light eyebrows, and waving tufts of hair. All 10-year-old boys have the same haircut. All teenagers with braces or glasses don’t want me to draw their braces or glasses. All adults are embarrassed to wait in a line with their children and then get their drawing done too — so I have to draw them pretty quickly.

These generalizations happen from a psychological and sociological viewpoint but then find their way into my drawings. I have a certain way of drawing bangs that works fine, and for drawing ears. Most people’s eyes are similar (it’s the eyebrows that are different), so I can often draw them without looking. The same is true with shirts — I can draw a neck and shoulders without comparing them to the real thing.

But this is dangerous, from a creative standpoint. If I start doing it too much, I’ll miss an exception, and screw up a picture by not getting a likeness. So I try to keep it fresh. Racially diverse subjects are too few and far-between in the mostly-white fairs that I’ve worked at, but any variations on the standard 6- to 12-year-olds can be considered diverse in that situation. Teenagers are fun because they give you unexpected surprises — piercings, dyed hair, wacky nicknames (Uncle Jimbo is the oddest name I’ve ever included on a caricature). Adults often have beards or glasses, different hairstyles than children, or are balding. Sighting a truly unique-looking person standing in line can be a major relief.

Creativity, humor, and individuality should be the hallmarks of a good caricature. Oddly enough, people are often embarrassed or afraid to get their caricature drawn for this reason — because the humor works best when it’s poking fun at its subject. They think the picture will be completely unflattering and embarrassing. What’s even more odd is the revelation that, at least in my case, it’s often the opposite.

I’ve done a lot of caricaturing — at some high school after-proms and a few parties, but more often at county fair-type events. Each situation presents similar drawing challenges, but in every instance, I try to make the drawing favorable. I don’t hold anything back when exaggerating someone’s features, but I try to first get a likeness. Creating a picture the people will enjoy should be more important than poking fun at them. I try to keep in mind that people will want to keep the pictures and hang them up, hopefully for years.

What you might not expect about drawing a portrait of anyone — and caricature is just a stylized form of portraiture — is that looking at someone long enough to draw them gives you some insight into that person. Not that I’m claiming to read minds, but staring at someone for ten or fifteen minutes lets you know certain aspects of a person pretty well. Not only do you see how they act (are they nervous, excited, bored?), but while probing for hobbies and interests to include, you get a good, although cursory, look at that person’s interests and identity.

The most insight comes simply because you’re looking at the person with no goal other than to see them. It’s odd in a daily situation that you’d look at someone for 10 minutes without them getting a little freaked out. So caricaturing is like someone giving you permission to examine them.

While this has great potential to sound cheesy, what trying to draw someone does — which is completely unexpected — is makes you see the good features of that person. Attempting to make a favorable picture forces you to include the most favorable aspects of someone. Not just the favorable aspects of their face, but their personality as well. Theoretically, I could draw the ugliest person in the world — someone so ugly that their mother dropped them off at the fair, swearing never to return — and still end up with a beautiful drawing. It’s harder to make a favorable portrait of someone with a bad attitude than someone who’s unattractive.

The strangest part is, it’s never intentional. I’m not trying to flatter the person. Indeed, it’s really hard to try to improve on someone’s features and still get a likeness. It’s easier to sincerely like the person — which, in almost all cases, happens when you’re affably chatting with them at a fair — and then just try to get a likeness. Their best qualities will tend to come out. I’m not unique; I’ve heard other artists mention this too.

Of course, the artist can never know just what you, as the subject, are going to like. There’s no way to anticipate if someone has a hair complex and freaks out if I draw a strand out of place. But I’ve never created a caricature that I wasn’t proud to give away. And I’m not even doing this as a career. Professional caricaturists have more expertise, which shows in their drawings.

So the next time you walk by a caricature booth at the mall or your local community day, don’t pass it up because you’re embarrassed or afraid of how the picture could turn out. It’ll most likely end up looking better than you expect.