I like the mysterious elements of Tolkien, so Allatar and Pallando to ask about their time in Middle Earth, a Balrog to ask how many of his kind there were while having a look to see if he had any wings, Fimbrethil to ask what happened to the Entwives, one each of the Ironfists, Stiffbeards, Blacklocks and Stonefoots and any long-lived Avari who remained in the East to find out more about their culture and the history and geography of Rhun. I would include Radagast and Tom Bombadil but I doubt I would get much coherent information from either.
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