To that end, the one online media property that continually impresses me with its clever names is Gawker Media. I don't know what Nick Denton's method to his madness is (scotch?), but he continually comes up with great names for his properties. Not all of them are home runs (cough....sploid...cough), but alot of them are really good.
The great ones, Jalopnik, Gizmodo, Jezebel, Wonkette, Gawker (for its original celeb sighting repository function) make the tone and subject mater of each blog obvious to the readers, but in a non-obvious way. That's a tough trick to pull off. How easy would it to have just used a name like "chickstuff" or "girltalk" or even "women's daily" for the women centric blog? All sort of blah. But Jezebel? Now that's a name! Unencumbered, descriptive, non-obvious, immediately informing, emotional, whimsical, etc. All great qualities in a name. And perhaps the most impressive part of each of the aforementioned names is that they all appropriately connote the editorial snark of each blog.
Now with that, I don't like all of the names he chooses. To wit, Lifehacker, Deadspin and io9 fall in that category. While I do like the blogs themselves, especially DeadSpin, I don't love the names. But even when he doesn't come up with a good name, its not for the typical reasons. Most crappy names are a result of their being too common or too descriptive (e.g. business.com, shopping.com, etc.). That's certainly not the problem with these names. They're non-obvious, but don't work for other reasons (IMHO). And if you're gonna miss, you should always miss taking a swing.
Anyway, as we think about our future name and brand, it would be nice to be able to think like Denton and come up with something great. I wonder what his brand of scotch is....