the boss can detect headphones going on your head and music starting from 50 feet away and instantly be behind you with a burning question that doesn't make any sense.

I'm sure you realize that the question doesn't make any sense because they had to think of it on the spot, just to prove that you can't wear headphones in the office due to all the important ambient office talk you need to be a part of.

One of my best, most competent bosses once said to the team "I don't understand how you guys can work while listening to music, but as long as your output stays high, I'm not going to interfere."