Originally Posted by Sniggles
Honestly, I think it has to do more with the divide between the rich and the poor than his actions. A rich businessman - especially a president of a billion dollar corporation - portraying a homeless guy while harmless still comes off as pompous anyway you look at it. It's nothing that should ruin your day, but it shows the level of class that he has.
I do see it that way too. I don't think it was meant to be mean spirited or insulting though.