I was reading through the thread on those who submitted their worst jobs so I've decided to come up with your "worst boss".
I had a boss not so long ago that was such a stinker for discipline, that it actually caused me to be stressed out and worried. You would never know what mood he was going to be in that day and you are never sure whether you were doing a good enough job. As my job is mainly a secretary that mostly types (whether working in a legal environment or not) at times, when work piles up, tensions tend to get high. However, my old boss was one of a kind, if I spelt a word wrong he would call me into the office and ask why I spelt it wrong. He would send me an email everytime I got something wrong - no matter how minute and ask me to see him. There was even one time when I was reprimanded by one of the other solicitors via email about a cheque that was sent to the wrong place. The email was copied into my boss's email and when my boss arrived for work and saw the email, reprimanded me as well! I think once would have been enough. I was asked to type a file note for a file but had forgotten to print it off for that day. Well when the next day arrived my boss asked in a calm manner whether I had done the file note, I confirmed that I had and then he shouted out "WHERE IS IT?" - nasty man.
I can't believe that I put up with this for 4 years! When I finally got another job I was so relieved it was unbelievable and I feel much happier in myself for leaving too.