I've had some doozies for bosses, which have led me to a firm belief in the Peter Principle.
I worked at a large private university in the library system. My boss was about 50 at the time (younger than me now), but dressed and acted like a much older woman. (I thought she was 70 when I first met her.) I was 25 at the time. The first day of work she pointed her finger at me and yelled, "Don't think you're going to take my job, young lady!" I was taken aback and blurted out the truth as I saw it, "How could I possibly take your job? I'm not qualified for it! Plus my job is a lot of pr that you don't do. Apples and oranges." She calmed down a little. but she always seemed threatened by me or frankly, any younger woman. She liked men, especially older men -- she was sweet as pie to them. But amongst her behaviors:
1. She would run laps around our reading room when she got angry. In front of patrons. She often got angry.
2. She once told an employee that it was too bad abortions weren't retroactive.
3. She would berate me for wearing certain colors because "Librarians wear forest green, tan, black, grey and navy blue. NO OTHER COLORS. Also you must always wear a suit, no separates, no dresses." I went to her boss and asked if these were work rules or not. He told me that she was nuts and to ignore her rules. He also told me that one of the reasons I'd been hired was that they wanted a younger face and attitude for the library and the way I dressed -- which was professional but appropriate for my age -- was definitely helping boost the library's image amongst students.
4. She would say that gay people should be shot. One of our coworkers was gay (and closeted). Nightmare. We would always tell her to stop and she would flounce off.
5. She once commented that she liked to go to the symphony and the opera, but had no one to go with. A few days later, I was talking with an elderly gentlemen who was a widower and mentioned that he and his late wife had lifetime season passes for two tickets to the opera and symphony, but he didn't have anyone to go with. Aha! I thought. I can make my boss happy. She loves older men, she loves the opera and symphony, perfect match, right? So the next day at work, I tell her about this opportunity and before I've finished, she starts screaming at me, "I DON'T WANT TO HAVE SEX! Why must you always talk about SEX!" At that point, the entire area fell silent. I said calmly, "I was not the one talking about sex. I was offering you an opportunity to do something you said you wanted to do -- go to the symphony and orchestra with someone--" She started screaming again, "No, it's all about SEX!" I looked at her and said, "No, not to ME." And walked away.