On a more serious note, I think that any such nonsensical award should have unknown criteria. What does it really take to earn those awards listed from other divisions? I have no idea how to get "Apple Bottom Jeans," and any such TF2 award should follow this criteria. Sorry Noise but I think your notion behind the "Late" award for reposting a topic is farmable. Let's face it, some people *cough* Darth *cough* do farm awards. Honestly, the system relies upon it. That's why we award commendable actions. We want players to be active in Vent, thus the "Ventrilo Regular" award. So creating an award for some poor sap who reposts a topic will only encourage that behavior.
To be clear, and to give full credit to Noise for this idea, I like the overall concept of having a "fun" award. But let's make it something vague, unfarmable, and definitely unique to TF2. Yes, I'm talking about hats. I personally like the title "At least I got my hat". "At least I have a hat" works as well, as does "Your face is a hat". And we can leave the criteria up to Leadership/AT/EC.