Luckily, I have not had any jobs that most people would consider awful. My first job was at a local 5 &10 (in other words, for those who don’t know what that is, it’s a discount store like a smaller Walmart). It only paid $3.50 per hour, which was a few cents more than minimum wage at the time (I was 16) and so I would work all day for take home of $18. It was boring but it was not awful, for the most part.
When I was in college, I worked part time for an attorney. He specialized in elder law and SEC types of things. He was very smart and I learned a lot from him. I was his typist and I was the only person he had working for him at the time. I wanted a job that was about 20 hours a week but he really needed more like full time or almost full time. On some occasions, I couldn’t leave until something was finished (lots of revisions as he would re-think and revise often) and on nights when I had a test or paper due the next day, there would sometimes be an argument.
Both of those jobs were not awful but in my scheme of things, they were tough. I guess as far as tough goes, the hardest was CPS worker. Details are too mundane unless someone really wants to know, then I’ll tell you, but it was tough. It paid well, though so that is a mitigating factor.