Mine has to be the encounter at Hardware Town, I just had to https://www.youtube.com/watch?v=bizTZ3AZX_k Funny as hell. I love the way he says shut up, like "sssutupp"

The guys who did this scene need a medal or something, there's precious few encounters like this.

When I realized I could keep the Drinkin' Buddy bot and send him to my settlement instead of turning him in. No XP from the mission, but FREE BEER! Better stat beer, free, resellable, a lot of it.

YES!!! When I saw that option, I said to myself, there's no way I'm going to give that thing up. Especially since I already had a recipe.

Only thing, the darn mission won't clear. Guess I'll have to go to the guy and tell him raiders shot the thing up.

BTW, enjoyed how my first reaction is, 'Know how long since I've had a cold beer.'

During the MM quest line at the battle for the castle, I had my settlers turn on me at the end. I must of shot or naded one of them in the mayhem. I reloaded a save and went thru the battle again and right at the end I toss a nade at a group of Synths as one of my settlers is running towards them and it injuries him not kill him. We finish off the last few synths and all the settlers turn red and start attacking me again. Not the MM in the castle mind you just the settlers.

Thankfully I hadn't upgraded very many of their weapons and I just sat there for a moment with their .38's bouncing off my PA. I finally thought to myself, you ungrateful M'F'ers. I then pull out my minigun and mow there ass down. The last few backed down and ran off into the castle. When it was all said and done my once 20 strong settlement at the Castle only had 6 left. I had some overcrowding problems at some other settlements that was quickly resolved after that fateful day.