God. This reminds me of the first (and so far only) time I ever GMed.
So this was freshman year of college (about 3 years ago now). I watched some Matt Colville and decided to make a D&D 5e oneshot dungeon of my own. I knew it would be driven off the rails the second my players showed up with their two monks, Sandy Ravage (a half-orc) and Timmy Turnbuckle (a halfling), in a Wrestlemania inspired tag team.
The plot was simple. The duo were at a bar when a man came in and announced that his daughter was kidnapped by cultists looking for a virgin sacrifice, and that he was willing to pay anything to get his daughter back. Pretty bog standard stuff.
The two find out that the cultist base is an abandoned castle. When they get to the castle, the first thing they do is ask the guards what they're doing. Their response showcased how finely honed my improv skills are.
"We're guarding our secret base while the ones inside perform a virgin sacrifice to bring our dark lord into the world! But now that you know our secret, you must die!" *cue battle*
Several wrestling moves and two dead, loose-lipped guards later, and they're inside what appears to be a giant room with ornate decorations. This was where they learned that the head cultist's name was Jeff Flavors. This is important for later.
Besides that, there was nothing else of note other than a sphinx guarding what appeared to be a wall. Said sphinx demanded that the two of them answer this riddle:
"A lilypad doubles in size each day. In 28 days, the lilypad will cover the entire pond. In how many days will the pond be half covered?"
Timmy Turnbuckle's character guessed the answer to a riddle that took me several days to figure out, a feat which I'm still salty about to this day.
The next part I was particularly proud of when I was making the dungeon. Being a history major, I decided to take inspiration from Louis XIV's castle. There was a long hallway full of nothing but portraits of lords past. However, they eyes were cut out of the portraits, and there was a large indentation inside the portraits, meaning that a cultist would hide behind the portrait, watch them from the eye slots, and pop out and ambush them.
The problem was that, like an idiot, I had them ambush the party one at a time. So after the two monks took care of the first portrait, Sandy Ravage proceeded to stick his fist into every painting, the monks proceeding to beat the ever loving shit out of every innocent painting they came across, and a few zealots along the way.
Eventually, the two made it to a room with a horrible demon inside it. I believe it was the Hunger Maw from Volo's Guide to Monsters. This was the most normal part of the dungeon, with the two of them, in bad 5e encounter tradition, beating the ever loving crap out of a damage sponge while the monster tried to attack them.
Eventually, they entered the sacrificial chamber, where they saw some cultists and their head cultist trying to sacrifice a 6 year old girl to the demons. Upon hearing them burst through the door like the Kool-Aid Man, the head cultist turned to them and shouted, "How dare you disrupt our ritual! I, Jeffavorite Flavors, will strike you down!"
This is what I considered comedy. And no, nobody else laughed, despite the rest of the dungeon being treated like Mystery Science Arena 3000.
Anyway, they beat the boss with more painful wrestling moves, the girl was saved, and the tag team got some publicity. Though my dungeon was objectively awful, we all had a good laugh about it.