Interesting thread!
If we could pick anyone living or dead, I'd pick Walter Benjamin. Most people haven't heard of him, but he's probably on of the greatest minds of the early 20th century, and died trying to escape Vichy france during WWII. I would have also LOVED to meet Edward R. Murrow.
As for living people... Bill Clinton, Jon Stewart, Dan Rather, Ted Koppel (for sure!).
I would like to meet George W. Bush, but not because I admire him. What I admire is his astuteness in the world of politics--basically how he has managed to convince everyone that he's "down to earth" and "one of them," when he's actually an old money blue-blood New Englander with an Ivy League education. Also, I'd like to know how he sleeps at night, but that's another story!