It's also a sign that your culture is able to deliver a fun feature, just for the sake of it. I've worked several places where things are so fragile nobody would dare make any change that wasn't strictly necessary. That's not a good sign.
Bearing risk in mind, there's probably a reason that it's acceptable to implement the DVD logo on the front-end client but poor taste to humorously update HTTP headers, for instance.
(That said, I tend to stay in the camp of "any path that can be hit, I'll eventually have to support.")