As the titles states, any town names that either make you laugh or cry, just plain dire, or completely way out there.
I'm going to start with Hole, in Norway. Now before Vimes chips in, yeah I know it has a different meaning in your language, but here in Australia it would imply that is a **** place to live.
This one gets a mention. It has been done before, but it is pretty funny (and mods I'm not trying to avoid the filter in anyway ). But my all-time favourite, the name of a hill in New Zealand (*clears throat*):
Good luck pronouncing that last one correctly!