Lemme think of my favorite DMing moments…
Okay. First one was a long time ago, in which the PCs have started investigating a murder, and the murderers hire a gang of thugs to strike back. They handily defeat the thugs, find out at what bar the thugs were hired, disguise themselves, and go to the bar, obviously trolling for rough work.
Sure enough, the murderers show up to hire some more mooks, and with some fancy roleplay, the PCs manage to get themselves hired to assassinate themselves. They go along with the murderers to a rooftop, where they set up an ambush for themselves, at which poitn they realize they hadn’t really figured out what to do once they were there; finally one of the PCs says, “Ah, screw it,” and starts shooting their employers. Their plan took me completely by surprise, and it was a great rooftop fight.
Moment two: From the same game, one player’s out-of-town boyfriend was in-town, so I wrote up a quick guest-appearance character for him to play, a city guard; and as a bit of throwaway character motivation, I gave him a daughter with scary and deforming birth defects that was hidden away in his house. I never expected it to come up in play at all, but rather would be something to motivate him to be an assiduous city guard so he could earn more money to take care of his daughter.
Instead, he tremulously asked the PC cleric if he could take a look at her, and we ended up having a very touching scene that ended with a PC giving the daughter a prized magic item–a hat of disguise–that she could wear in order to mask the deformities.
Three: One PC is, unknown to him, infected by a wererat; the PCs have also angered a mind-controlling demon who realizes that the infection has occurred. So he follows the PCs, and on the night of the PC’s transformation commits bloody murders and sends people enough bizarre visions that they can’t figure out who’s turned into a wererat or what’s going on.
So a couple of them go outside and pull out a regular dagger and slash their palms with it, on the theory that the wererat will heal up from the damage (they’re wrong, but I don’t tell them that). One by one they pass the knife and cut themselves to see what happens. Then the last PC comes out, and they hand him the knife and stare suspiciously at him, waiting. And he’s all, “What the hell is wrong with you psychos?!” and they’re all, “DO IT, MAN! JUST DO IT!” It was some of the best paranoia I’ve ever gotten.
Daniel