Two that left me snickering;
The first was at RAAF Edinburgh in Ozzyland a decade or more ago at night with a P3 Orion conducting night circuit training. On downwind the pilot advised the controller "for information we will be conducting a "lights off approach", whilst lining up on finals, the controller promptly turned off all the approach and landing lights....a surprised (and probably subsequently ticked off P3 pilot) overshot and the rest was probably more entertaining at the bar afterwards!! If it wasn't obvious...he actually meant his own landing lights!
The other was more recently here in the middle east when the many round the world ballooning adventures were being conducted in the last year or two. When one of the balloons crossed into the airspace (quite successfully following the airway I might add!), a controller drew the attention of another controller to the event and particularly the balloons spritely groundspeed of 160 knots or more....to which the controller asked (quite seriously I might add!) "I wonder if he has got a head wind or a tail wind?"
