This is basic strategy really - being a dick to people will almost never bring you closer to a goal you've set, which means there's no point in doing it. The success rate of "calling people stupid until they agree with me" is quite low...
I think it depends on your intent. Being a dick is a clever strategy if you want attention. Being a dick by calling someone very popular (or visible) stupid gets you attention. Instead of people ignoring the dick, they pile on and then criticize him -- which is giving him attention. Then, people who find some reason to agree with him pile on and defend him. Bamb, the dick has now usurped some of the targets authority.
(P.S. I am not defending this strategy. I find it annoying -- but entertaining in a checkout line gossip rag type way.)
I'm completely sure that Kanye has ADD. That was in no way to his advantage, and if he thought it through the way non-ADD people do, he wouldn't have done it. It was a strictly bad play.