My choice would be Theodore Roosevelt because he was such a badass leader. Although I might be intimidated to dine with him.

Also, Richard Brandson, because he is such an energizing leader without being overpowering. Anyone who has heard him talk can see that he is very approachable and down to earth. Nonetheless, he seems to be masterful at motivating large groups of people to accomplish great things–hence all of his companies and sending people into space!

Sean Evans, the host of Hot Ones. He is great at interviews.
Joe Rogan, is also probably someone who would be fun to talk to.