I've got a bug in my ear. "Celebrity DM" Chris Perkins was asked an interesting question: "If you could DM anybody, living, dead, or fictitious, who would you choose? He chose Lovecraft, Obama, Oprah, his interviewer, and Gary Gygax. Sadly, he chose not to elaborate. Intrigued, I decided I'd make my own list, with explanations and apologia. Throughout, I'm choosing them based not on who they are individually as much as who they could be as a roleplaying group. Therefore, any overlap should be strictly synergistic.
I choose Dante because I want someone who pays attention to political maneuverings, and also because I want someone who can completely immerse himself in the game, who could take the threads I'm offering and run with them. Dante demonstrates his ability in the Commedia to incorporate earlier ideas and spin them as his own, something so wholly necessary in roleplaying games that two others on this list will have that feature.
I pick Shakespeare not primarily because of his writing ability or his creation of many characters, though those things are quite helpful. I'd love to play in a game he DMed more than any other person on this list, but that's not what counts here. Many say that what made Shakespeare such a great playwright was that he was first an actor; his plays are still widely loved by actors for the freedom they cede to the performers, the variety of interpretations they allow. I want a player in my game who can fully embody a character, to make it his own--not simply play somebody else's character, but create it on the fly. And, of course, I think he'd like to hang out with Dante, too.
Queen Victoria ruled for 63 years as monarch of the United Kingdom and Empress of India, arguably the most powerful person of her day. At the same time she oversaw politics and wars, she managed her family and, when necessary, ceded power to the people. Every group of players needs a leader: someone to organize and strategize. I pick Victoria over either of the Elizabeths for a reason: Elizabeth I was a political actor primarily, even though she fought the Armada she will be remembered primarily for her politics; I've already got Dante for that. Additionally, she was in many ways a tyrant--not someone I want to sit across the DM screen from. For all of Elizabeth II's diplomacy, she doesn't wield enough actual power to be a strong leader. Persuasion and logic, sure, but not muscle. I imagine she would enjoy meeting and spending time with Dante and Shakespeare, to boot.
Yes, I know that I'm losing any gusto I have on this one. It's my list, so back off. After such incredible luminaries of the past, my fourth player needs to be Doctorow. For one, he seems like a person I'd just like to hang out with (Shakespeare would be another--but not necessarily Dante or Victoria), but that's only a secondary reason to be on this list. Doctorow is both a writer and a programmer. The writing he's done has been primarily from taking older concepts and spinning them off into completely new ideas. Additionally, he's collaborated with other authors more than occasionally, and is quite vocal in his praise of other authors. He even teaches at the Clarion SF school, showing his dedication to helping others. This should make him great for not only creating and maintaining his own character but also for working with the others in this group. Add to that his programming background, and he could help explain the rules to the others, a thing of no mean importance. As an activist and a contrarian he could also balance Dante and Victoria if power struggles or, with his seemingly limitless cheeriness, hurt feelings. Finally, he's he only person I've mentioned so far who has actually role-played (in the modern sense). I imagine he'd like to meet Shakespeare and Victoria, and also Dante. His directness might rub Victoria the wrong way at first, but if they're on equal footing socially, she'd get the hang of it; she was strong willed, but adaptable.
4. Tie: Genghis Khan or my brother Will
Okay, sure. Have I lost all my street cred? Out of anyone in the world, and I can't choose between Genghis Khan and my own brother? For one: we need someone focused in both tactics and strategy, and could also get along with the people. He also was capable of organizing and getting along with others, which is an important skill. As for my brother, for one, he's my brother, so that's nice: someone I can depend on—not to obey me as DM but someone who's already a known quantity. Furthermore, Will has expertise I've seen in understanding new systems quickly and easily, and often showing off how awesome he could be, both in the rules and in his characterization, as if his single modus operandi was "just be awesome." How would they work with the others? Genghis Khan would get along tolerably well with Dante (a former soldier) and Victoria (a head of state) Of course, depending on which age Victoria would be, he might also hit on her, but she's a girl in a game group, so that's practically a trope, and she could certainly handle rebuffing him. Will, great at just walking up to people and being cool, would get along with everyone, especially as a historian: the guy was a double-major in history and philosophy with an English minor. He would probably embarrass himself less around Doctorow than I would, honestly.
Of course, there are a few people I'd simply refuse to DM, not for personal reasons, but for gaming reasons.
I would never play in a game with I would never play in a game with Machiavelli. Never. Even with apologists who say that he wasn't horribly ruthless and evil, I think that "not evil" still isn't good enough. When roleplaying, I don't want to have to metagame for control, I just want to play. If Machiavelli were to show up at my table, I'd rather walk away than play with him.
Neither would I ever game with Enrico Dandolo. While I respect his canniness, he seems like a person who, in a roleplaying setting, will do what's best for his character—not just in spite of party interests, but spitefully in direct opposition to party interests. He seems like one of those players who'd say, "Well, it's just in my character's nature to sell everyone out to the necromancer." Certainly not.