I’ve played RPGs for about 34 years, so considering all the people I’ve played with over the years, it’s hard to pick and choose a few people out so many great gamers. They’ve all brought different perspectives and skills to the table.
However, of people I have never played with, I would love to play with Ken Hite, who I knew back in my freelancer days but never had a chance to play with. As the master of the Cthulhu mythos, a great historian and an amazing game designer, playing with him would be blast.
As well, although he’s no longer with us, it would be great fun to play with Robin Williams, the king of comedy, the master of improvisation and an avid role-player. It would be an experience I imagine that one would never forget.
And finally (since three is the ideal number of players), our GM would be D. Vincent Baker, the originator of Apocalypse World and the creator of a new way of playing games. I think it would be a fun game.