I have been binge watching star trek voyager over the last couple of days, and I had a funny thought.
“You know who would make a great dungeon master? Q!” (From the episode where Q helps Q commit suicide)
He could make you feel the story, hear the monsters, heck, see the monsters 
The I thought, “You know, Genie from Aladdin might be better, he wasn’t so cruel.”
So, if you could pick any person (Living, Dead, Fictional, Real) to host a night of D&D, who would you pick?
Joss Whedon.
Ooh, I didn’t even think of brilliant writers. That would definitely be a fun choice.
Skald the Rhymer. Except you’d have to replace the “20” on your die with “pecan pie”.
E. Gary Gygax or Ed Greenwood
Greenwood I can see. But Gygax? You’d wanna play with the dude who thought up the Potion Miscibility Table?
See, I’m jinxed in a thread like this. I’m the designated DM (well, GM in most of the games I run). It’s tattooed on my forehead or something. I’d sit down in front of Q or Gygax or Whedon and they’d say “Oops, sorry. Didn’t know you were coming tonight. Here’s your DM screen and mission notes.”
Anyway, I would NOT want Q or the genie running things. Part of what makes games enjoyable to me is the imaginative process. I don’t really want to be shown an entire rendered scene, because I want to imagine it with my own flourishes. In fact, some of the best moments in gaming happen when a player says “I grab an apple off the tree!” and I say “Off the wha- Oh, right. Yes, there’s an apple tree and you grab one.” It’s meant to be a cooperative game. (In fact, that’s one of the things that’s relegated me to forever-DM-dom.)
So who would I like to game with?
HP Lovecraft. I’d bring three characters just so I could savor each horrific death.
Joel and Ethan Coen.
Absolutely. I wouldn’t expect to survive the adventure. Gygax was overly fond of the “turn left and die for no particular reason” style dungeon, but he’s the guy that at least formalized the game.
And if the game just happened to take place in Colorado or Washington State, so much the better. 
J.R.R. Tolkien. It pretty much all goes back to him anyway.
Isn’t that basically what the holodeck is for?
Since my last name doesn’t start with “Pi” and end with “card,” Q would get bored with me after roughly three seconds and probably leave me to die in whatever fantasy world we were ‘playing’ in.
The Penny Arcade guys seem like they’d be a blast to play with.
Abed from *Community *and Moss from The IT Crowd were both shown to be pretty great DMs.
I remember when Gygax started writing articles for Dragon Magazine, after the introduction of 3rd Edition. It seemed like the times he remembered most fondly was smacking down players for taking pride in their characters. I don’t think I’d want him as my GM, not for very long.
I’ve played with Gygax as the DM at a convention. It was very straightforward. Attempts at imaginative solutions didn’t go far. That was, to be fair, also the fault of the majority of the other players.
My first thought was Lovecraft, but the a-hole probably would refuse me since I’m a bit brown for his tastes.
My next choice is M. Night Shyamalan. His later movies may suck but he has the mindset, IMO.
James Earl Jones
I can’t think of anybody I’d rather have as GM than Neal Stephenson. He can tell a story in a richly developed realistic world, he understands the roleplaying genre, and he takes a big interest in the study of historical weaponry and fighting techniques. Now, as a player, a self-styled expert in weapons can be obnoxious even if they have interesting things to say. But a GM can use such knowledge to enrich a fictional world.
Cool. What did you have to do to get a spot at his table? Just random luck, or what…
He probably put all of the applicants on a big percentile table and rolled.
I thought about Tolkien and decided no. Tolkien is the kind of GM who spends the first session reading four hours of painstakingly detailed backstory for the town you just passed through.
That might be a little unfair - all that backstory and notes made for excellent novels once it was properly edited down, but does a GM at the table have time to appropriately edit himself? I guess I’d have to see, but my guess is that he’s too much in love with minutia for him to translate novel writing into gaming.
I favored Lovecraft because he’s used to leaving things unexplained and to working in a short-story format.