This type of person was/is probably in a fraternity. They may hold an esteemed position at a company. He is a pompous asshole. However, he is also fun. He likely surfs, shotguns beers, and smokes weed. He probably spits on the sidewalk and talks too loud to his clients/friends on his cell phone in a quiet place like post office or elevator.
2. the asshole that you still hang out with, but you're never sure why.