The management team in my company is really weird. As a result of my mom being a manager, I get to see a lot of the strangeness firsthand.
Last week it was photoshopped images of Vladimir Putin on various things. Bearshark, meteor, space unicorn, ritz cracker, crane, etc.
In the processing department (where my mom's a manager) there's occasionally "Unfiltered Friday" emails that go around. Images from the internet that express frustration in amusing ways. One of the most recent ones was the picture of a tote bag that read "God must love stupid people, he made so many of them".
At my last job, another girl and I were the Phantom Editors. We'd always have pens on us, and any official or semi-official note that got posted in an employees only area (break room, clock-in room) would be viciously edited and corrected. With commentary. Even if the managers knew who was doing it (I'm not sure if they did or not), they never told us to stop. It was amusing for everyone.