Most of the really "interesting" stuff that I ran across during my career in security was during the six years that I worked at a really high end hotel. Myriad weirdness was seen and snickered about, and it's genuinely hard to narrow it down to a single event.

One of the single most random events were a pair of women in their early 20's that rode an elevator for a while, stopping at various floors and accumulating random bits of furniture from the elevator foyers and nearby room service carts. By the time all was said and done, they had set up a table and chairs *in* the elevator, complete with a vase of flowers and a plate of h'ordeurves. Then they left.

One of the teachers was behaving very inappropriately towards his female students. We at the school newspaper wrote a story about it. It was censored by the principal. The journalism teacher argued that our paper was a forum for student expression and could not be censored by the school. The principal disagreed. There was a big hubbub about it and in the end the story didn't run. The teacher in question was also the town sheriff, so that might have had something to do with it.