I've had a couple of weird/crazy bosses, and beyond the "buy my wife something for our anniversary, here's the AmEx", the most obnoxious one was this: It was a secretarial job for a very, very tiny vitamin company. The boss was such an obnoxious weenus that during my interview, he gave himself a nosebleed getting worked up about how the items on his desk blotter were to be arranged for him each day. PENCIL HERE PEN HERE BLOTTER LINED UP EVENLY *nose begins to drip blood as eyes bulge and blood pressure gets high* (Cocaine? Who knows. Probably.) I took the job with misgivings but it paid well for the time. Found out a week later that they'd gone through eleven secretaries in the past year. So bossman and his doctor buddy go skiing in Colorado somewhere. They have a rental car, like you do when you go out of state. Turns out, they both got drunk one night, and the doctor buddy (who was not on the car rental policy), ends up somehow scraping the vehicle from nose to tail on a parking structure pillar. I'm instructed to call the car rental company and tell them that the valet parking kid did it. "Do whatever you have to do to convince them. The car was all messed up when we got it." Me: But...didn't Dr. XYZ do it? You told me Dr. XYZ was "a little loaded" and that he's the one who sideswiped... Him: YEAH SO WHAT, I'M NOT GONNA PAY FOR DAMAGES ON A MERCEDES, DO YOU KNOW HOW EXPENSIVE THAT WOULD BE AND MY INSURANCE WON'T COVER IT SINCE HE WAS DRIVING, SO JUST DO IT So I called the rental company, told them exactly what happened (drunk Dr. XYZ and all, and the attempt to shift blame to the valet kid), then went back in and told my boss that despite my best efforts, the rental company was intransigent about it and that they said they had "video" so shut up. I ended up quitting a few weeks later because the guy was absolutely insane. The office staff tried offering me a couple bucks more an hour (big tunes when you're making $13/hr back in the 90s) and I was like, nerp, gotta go, enjoy your cray. So what's the weirdest, most obnoxious, or illegal thing your boss has ever demanded you do?