I worked at a startup where I was largely left alone to get my work done, and things went along pretty well until the founder decided that I needed a manager and put me under the management of a loud, brash guy who did a lot of posturing and played a lot of power games but didn't seem to do much in the way of managing anybody. My work was unrelated to his area of expertise so fortunately we had very little to do with one another, but periodically he would come by to "check in," which generally consisted of standing outside my cubicle and insulting me and laughing at his own wit.
Our funding situation was touch-and-go, so it didn't surprise me too much when I got a call from him one day when I was working off-site. He said "I'm really sorry to have to tell you this, but our funding fell through and they're shutting us down. You can come in tomorrow and pack up your stuff." I reeled for a minute, asking the usual "How did this happen?" questions, and eventually he started laughing and shouted "April fools!" It was, in fact, the first day of April. Without thinking, I said "You're a dick," which only made him laugh harder.
A couple weeks later there was a round of layoffs, and he was replaced by a really nice guy who knew exactly what he was doing and was a great manager. A couple weeks after that, our funding fell through and they shut the company down.
I'm not entirely sure who had the last laugh...