I spend all weekend thinking about this challenge and I did come up with a few people I would love to sit down and have a drink with
Oscar Wilde would be my first choice. Over a glass of wine I would ask him what possessed him to marry and then coming out of the closet by writing The Picture of Dorian Gray. Its implied homoerotic theme was considered very immoral by the Victorians and he must have known how it would be received.
Sir Francis Drake would probably have a beer with me. To sail to unknown parts of the world being part slave trader, part pirate he must have many a tail to tell. I would love to know what drove him to set sail for the new world.
Marilyn Monroe I would invite for a martini. A women envied by many, loved by even more and died way too young in such a tragic manner . I would love to know if there was more to her then that supposedly dumb blond exterior most people got to see. Of course her alleged affair with John F. Kennedy and how she died would be part of the conversation