Here’s a cool site: Identifont, an online tool for helping you find a font when you can visualize it but don’t know its name. If you have an idea of a font you’re trying to locate, Identifont will throw a bunch of questions at you — i.e. “Does the Q tail cross the circle?”, or “Does the upper-case ‘J’ extend below the baseline?”. As you answer them, it slowly narrows down the font you’re describing, and then presents you with it.

As it turns out, it doesn’t work that well. I tried to describe my favorite font, Copperplate Gothic, but even though I answered the questions pretty accurately, I couldn’t get it to spit out that font. Instead, I got Carlton, the font pictured above.

That’s when I realized that Identifont may be more fun if you use it simply to discover new fonts. You answer the questions basically according to your taste, and then you sit back and prepare to be surprised by what Identifont finds for you. It’s kind of like the flash-card techniques that MBA students in the 50s used to generate new ideas. They’d take a problem they were trying to solve, and then have someone pepper them with various questions, some relevant and some not; oftentimes the seemingly irrelevant questions were the ones that made them go “aha!” and arrive at a breakthrough, because they encouraged them to think in unconventional ways. (Trivia: Marshall McLuhan created a deck of idea-generation cards much this; they were issued in a very limited edition and today are worth some insane amount of money.)

In the case of Identifont, I was trying to use the tool to drive at Copperplate Gothic, but I wound up with Carlton — a font I wasn’t looking for, but which I rather like, since it shares some similarities but is nonetheless different. Even though the machine got it “wrong”, it did something creatively cool. It’s much like how collaborative filtering and machine intelligence can lead us in interesting new directions. Our Tivos find shows for us; Amazon suggest books based on what we’re surfing. Sometimes they’re hilariously wrong, but much of the time they’re useful in a key way — because they knock us slightly off our expected path.

I’ve often argued that artificial intelligence is best when it remains slightly unhuman and slightly alien, because that’s when it most contributes to our lives. If we wanted to get truly human-like advice on a good font to use or a good TV show to watch, we’d just go talk to a like-minded friend. That’s what other humans are good for! But machines think in much simpler and thus far weirder fashions than we humans do, so even when they’re wrong, they’re wrong in interesting ways. Sometimes, that’s even better than being right.

(Thanks to Tribblescape for this one!)