That would get at least one of us banned....lol.
If we wanted to avoid the potential flame wars, we could always just drop the headphone aspect entirely and just post random pictures of obvious FAIL moments. Or maybe, if we wanted to stick with audio, people doing dumb things with headphones or headphone-related equipment.
It'd have to be obvious what's happening in the picture at avatar-size, though, so that kind of limits what can be done with this kind of idea.
Failbruary, I was as first thinking pictures of triple-amped portable rigs, but Argyris is right, the size of the avatar image could be an issue.