I think I'd probably try to stretch beyond modern icons for the most part. I'd choose historically significant people. I'd enjoy smoking and shooting the breeze with Aristotle. Michaelangelo. Wolfgang Amadeus Mozart. Thomas Jefferson. Charles Darwin. Sir Issac Newton. Queen Elizabeth I. Henri Matisse. Marie Antoinette. Johann Sebastian Bach. Franklin Delano Roosevelt. And, just for kicks, John F. Kennedy, Jacqueline Kennedy and their son, JFK, Jr. That'd be a heck of a group to smoke with.