I have had a lot of interesting, hilarious, and downright awful things happen playing the stupid amount of hours I have with this game.
My most recent was realizing that a certain 'Doge' was refusing to leave. He would hang about my base, steal food, and then wander out into the map, only to come back and steal more food. Once I noticed the behavior, I kept watching him, and he'd wander out and about, and come back to eat my stocks. I arrested him, and he quickly joined ('such base, much potato') and proved to be a killing machine. Made him a hunter and he kept my colony well stocked in meat, and was a straight up killer when raiders dropped.
Maybe not funny, but both his name and seeing this 'hangabout' behavior for the first time, it's definitely a memorable experience for me.