Day 16 - Historical person you'd like in your group? What game?
This is a lot like the "Dream Team" of past players. It's a case of chicken and egg. Do you pick the game first, then find a historical person to match that game? Do you pick a historical person first, and then find a game to match them?
I'd love to play a historical miniatures battlegame against Napoleon or Genghis Khan. I'd love to engage in an elaborate costume LARP with Lord Byron (or even someone taken from us more recently, like Alan Rickman), or maybe a boffer LARP with Errol Flynn. I'd love to see how HP Lovecraft would see the way his mythos is portrayed in modern day RPGs.
There are so many possible answers to this question.
The way most of my groups tend to play, I could easily see someone like the comedian Robin Williams easily fitting into the loosely reined chaos, and I would be interested to see how far the envelope would be pushed, and whether it would end up breaking. I'd imagine we'd play something like HoL.
Day 17 - What fictional character would best fit in your group?
Perhaps the Librarian from the Unseen University (Discworld), especially if we were playing something that involved lots of tables and referencing, like Rolemaster.
Maybe, Inigo Montoya (The Princess Bride) in a swashbuckling Boffer LARP, because it would be awesome to improve the group's collective swordplay skills, and witty banter is always a plus.
If I was running a game with investigation in it, I want someone like the world greatest detective Bruce Wayne / Batman added to the group (or possibly Sherlock Homes, but depending on the incarnation of Holmes it could be a odd fit), because the current mob can't even pick up on the most blatant trail of clues that I leave them.