My first thought after reading this was, what would be the most uncomfortable game of DND I could muster? Here it goes:
DM- David Green, the CEO of Hobby Lobby
rogue- Sarah Palin- she wrote a book about it after all.
paladin- Jay Cutler- he would be very demeaning about the whole thing and then not care once the game started.
Wizard- Joel Osteen. I just feel like he would have a really hard time casting magic.
Barbarian- Mahmoud Ahmadinejad, president of Iran. Being a true life barbarian, we all know he would take it WAY too far.