[alook]

At a startup I worked at, one of my cofounders was an incredibly skilled designer, and he took a lot of pride in the design of our homepage. He spent a lot of time in particular finding the right fonts, and would often complain when he saw other company homepages with inappropriate font choices.

One April fools' day, we thought it'd be funny to make him think that we'd changed the company homepage to have a comic sans font. Of course it'd be going too far to actually change the website publicly, so we decided to set up a DNS proxy inside the company office.

We took our company homepage, recompiled a static site with comic sans, and hosted it on an internal server. Then we set up a DNS proxy that resolved our company homepage for requests coming from inside the office to our comic sans static site, but otherwise the internet worked normally.

We made sure that everyone else in the company would feign outrage when he came in and checked the website, so the joke lasted for a couple hours before he thought to check the website from his mobile phone. Later, he appreciated the joke and figured he should have connected the dots sooner and realized that it was April Fools' day.

[paulryanrogers]

We did something similar and the boss was quite upset. He said it disturbed sales demos and cost time and money. Which was surprising since he was otherwise a very chill boss who enjoyed all manner of fun and skunk works at the office.