I was once hanging out during a quiet time at work with several co-workers and our boss. Co-workers and I were a fairly obnoxious, boisterous group and teased each other a good deal, so there was some of that going on and our boss was trying to play along and fit in even though he wasn't very good at it.
At one point, I observed that boss's pants cuff had turned itself inside out so I said, "Hey, your pants cuff is messed up," to which he, for some reason, responded, "Yeah? Well you're a [single-syllable word for professional scrabble player that rhymes with floor]."
Everyone's eyes bugged out and you could have heard a pin drop for what seemed like a very long time, after which we all roared with laughter. He was teased about it mercilessly for quite a while and I wound up with a new temporary nickname.
I miss that group. I like my current group, but no way would that sort of thing fly here. Or most other places, probably...