This is a story from a job I had a few years ago. It was one of the most bizarre experiences I've had in the world of work, although unfortunately at the time I was too inexperienced to realise that most jobs weren't like this and my boss' behaviour wasn't exactly typical.
It seemed like a decent job, working as a web developer and general tech dogsbody for a local company. The company was pretty small, maybe twenty people in total. I was interviewed by my boss who seemed a nice sort of guy, if a little lacking in social skills. My first day passed uneventfully, and I was checking my email on my phone on my way home when I received an email from my boss, asking me how everything was "coming along". I was a bit confused about what he was referring to, but I replied that everything was OK and I'd update him when I got into work the following morning.
A long stream of emails between him and myself followed. He quizzed me on almost every aspect of my day, from how many breaks I'd taken, to what I'd done with my time, to what I thought of the current codebase and whether I'd thought of a solution for bug X, to a request to install some software on his PC for him in the morning. I must sent about fourty replies to him that evening. I stopped replying at around 8:00PM, having sent him an email that I was going out with my family for dinner. I was pretty freaked out by the barrage of emails that I had received and the fact that my boss seemed to think that my work day didn't finish when I left for home.
When I was leaving for work the next morning I opened my email on my phone and found twelve new messages in my inbox from my boss. The first one was another question, and all the emails after that were him progressively getting more frantically unbalanced as he asked me whether I was "there", why I wasn't replying, what was I doooing, why haven't I finished lunch yet, crescendoing with an, "Have you run away? If you are going to continue being this uncommunicative we will have to find another developer". I was halfway to work when I got a phone call from my boss. "Where have you been?!", says he, "I was up all night fretting! You can't just disappear like that!" I was pretty disturbed by this point, and also pretty scared that I was going to lose my first "real" job. I tried explaining that, you know, I'd gone out, and then I'd come home and gone to bed, and it's unreasonable to expect me to reply to emails all night. He tells me that they "value communication" in their company and that I need to "restructure" my home time to accomodate the "needs" of the company. In the future, he said, I was to "check out" with him when I was going to bed for the night, and to "check in" when I got up in the morning.
Needless to say, I only stuck it out there for a few months. There's a lot more bizarre stuff that followed, and I'm pretty sure my boss had some kind of paranoia-inducing disorder, as he freaked out whenever I left for my lunch and demanded updates on what I was doing every twenty minutes or so. In the few months that I worked there he spent more time at my desk 'checking up' on me than he did at his own doing work. The most weird part is that he didn't do it in an assholeish "I am your boss and you must report to me on everything!!!" sort of way, he did it in a sort of "scared you're going to 'run away'" sort of way. He actually asked me quite a few times if I was planning to run away. Bizzare. (apologies that this bit is in bold, I accidentally pressed something to turn it on and for some reason when I click the B button the bold doesn't turn off. A WTF in itself.)