I originally posted about this on Reddit, but figured I'd post it here too. A friend of mine was visiting and wanted to play D&D with me. I figured this was the first time to espouse the virtues of old school play and run some Into the Odd. We rolled on the race table from Two Goblins in a Trenchcoat, since I figured people would get a kick out of that, and I gave them each an extra d6 HP to start with. I started off with a brief "OSR means rulings not rules, and don't try to fight things" intro and off we went.
Adventure 1
I ran Quintessential Dungeon, slightly altered to include some "OSR-style challenges" from Goblin Punch, and with some random encounters.
-The Characters:
Silence: a dim-witted skeleton filled with bees
Jilly: a prosthyletizing orc.
Highlights:
-The gang got past a group of goblins by bribing them with one of Silence's skeleton arms.
-The two of them went crazy in the room with enchanted food and had a bunch of potion effects; Silence got super strength, Jilly grew an extra arm, and then they switched bodies.
-The gang almost got killed by a group of animated clothing, the only foe they actually tried to beat in a fair fight. Jilly went unconscious (strangled by a shirt) but Silence managed to kill the last of the clothes as her HP was ticking down to zero.
-The gang found an enchanted fairy circle with two children inside, who begged them to enter it and fight the fairies keeping them prisoner. They figured out its trick (anything in the circle is enchanted and will do anything to get more people in) by sending in their dog. They lured the kids to the edge, then bludgeoned one into unconsciousness and dragged her body back to town to get the reward money. They gave up on the other kid and the dog.
-They came across a gang of orcs taking a hobbit prisoner. They promised to ally with the orcs to fight a dragon, saying that Silence was a magical skeleton and anything that harmed her would drop dead. They tried to grab gold from the dragon's hoard and leave the orcs to die, but Jilly got caught in dragonfire and was incinerated. The hobbit, a magician named Stilton, became the player's new party member.
-Stilton and Silence managed to find all the gems and escape with the treasure!
Adventure 2
This time was with a dungeon, randomly generated on the fly from tables in Into the Odd and Maze Rats. The dungeon was a series of weird eldritch tunnels they found in a library.
The characters:
Godwin, an ex-cultist ironclad elf
Balthazar, a ratcatcher rookling skilled at picking locks.
They were accompanied by their 2 hounds and Balthazar's packmule (they rolled a lot of animals in their starting gear)
-They found a lake full of acid that melted anything non-metal. They later found some steel twine they tied to a fish hook to fish up the treasure: an amulet that made you grow octopus arms and a potion of super strength.
-They found a brain in a jar on a pillar, which revealed itself to be Clovis, a janitor who had been turned into a brain to answer questions 200 years ago. All he wanted was to see the sea where he grew up again. To my surprise the characters actually pried his jar off and carried him around on a mule for the rest of the adventure. He ended up being a helpful ally, giving them hints about weaknesses of various enemies.
-They found a cult of old men guarding an arcanum, the Babble Book that lets you talk to anything. Using some fire, they scared off the old men and got the book.
-They met a mercenary who they hired to come with them, making an absolutely massive party.
-They came to some pods that combined anything put in them.They put in their two dogs to make a terrible mutant dog that was confused and afraid. Balthazar combined himself with Clovis so the once-janitor could again feel and see the world, and promised to take him to the sea shore, but developed face-blindness due to complications with the transfer.
-They found a hallway made of flesh, which they used the Babble Book to talk to. It turned out to be the decaying body of an ancient Sun God, who only wanted to see the sun again. They used a flare gun, Balthazar's starting oddity, to make a hole in the ceiling. The Sun God thanked them.
-They found the rest of the cult of old men. Their massive party easily beat them up and took their treasure, then escaped to the surface!
All in all both sessions went really well! I was impressed by how quickly the group started trying to think outside the box to get around things and resorting to trickery or plans to get past enemies. I was also impressed with how well randomly generating a dungeon on the fly worked in the 2nd session- the tables provided in Into the Odd and Maze Rats are great, and it was fun when not even I knew what would happen next.