I tend to ask this one alot - it's a good way of getting to know someone. My one rule is that it isn't family or friends. Otherwise, I - like many others - would pick people whom I've lost over the years. You can pick any person - athlete, singer, composer, president, etc.
I would pick Bob Dylan, Ryan Adams, Bono, Johnny Cash, and... the last one's a wild card depending on my mood that day. I've been known to say people such as: June Carter Cash, Caitlin Cary, Jon Bon Jovi, Mats Sundin, John Travolta, The Edge, John Maynard Keynes (economist), John A Macdonald (first prime minister of Canada), Neil Diamond, Gary Allan, Nora Roberts, Tico Torres, etc.
I think Bob Dylan would be one of the most interesting people to talk to. You'd just have to get him to talk straight and actually open up. Though I've sure some of the half-truths and tales he could spin would be amazing in of themselves!
Ryan Adams... I was absolutely amazed by him for about a year up until he hurt my feelings in a big way last month. Would love to ask him why then after that was out of the way talk poetry, lyrics, life, art, literature, music, etc with him.
Bono has got to be one of the most interesting human beings - right up there with Bob Dylan. The man is such an enigma - it would be such an experience getting to sit down and talk with him. What would we talk about? Ireland (I long to go there), his charitable works (I support many of the same causes he does), decisions he made regarding music, life, literature, etc.
Johnny Cash... the man has quite the history. There are several contradictions I've read that I would love t have him clear up. It would be amazing to talk religion with him as he was a very learned man on the subject. He studied through many courses as well as did extensive home study. There is so much that I would love to discuss/debate with him. I'll always regret not having the chance to hear him perform.
I have various reasons for my other choices. One reason for some of them being to see them interact with one of the others on my list. I would have loved to see June and John's relationship in person - to see if it was really as easy and warm as I've heard and read. The Edge... he is such a talented guitarist and radiates such peace. He seems like such a lovely person. I would love to have a sit down with him and discuss philosophy, religion, literature, music, life, etc. I have different reasons for each...
So... who would your choices be?