The sad thing is that of all the representations, somehow the bear manages to look like the oldest and smug one.
Old in the way that he just feels like he is supposed to be a 50 year old, badly aged misanthrop.
I think it is a combination of eyebrows, eyes, the color blue and the bear's chin.
He puts so much emphasize on the eyes of the character, you can't avoid to see just how either dead or insincere his expressions are (e.g. when he is supposed to be happy) or how miserable, smug and angry he is, on which he puts the most emphasize. The overly large eyebrows just add to it.
Second, the chin. His chin looks like you just subconsciously associate it with something to see on a fat, old, miserable man who shouts angrily at the kids in his backyard. He just looks fat, ven if Dobson draws him at best chubby.
btw, I looked over his Minecraft thing. Just out of curiosity, because I really don't know much about Minecraft:
1. Is there also supposed to be more to it than just building stuff?
2. If not, how does that make minecraft different from the Sims?
3. Can we just agree on the fact that Dobson plays Minecraft and Skyrim because he wants to create worlds he has control about, instead of adventuring in worlds he may have none in and therefore are challenging?