I just remembered one I liked years ago. It was on an old wooden cutter that looked almost like it had been converted from one of those skinny wooden fishboats from way back - the 20's or thereabouts. It had an extremely robust and determined "Bulldog" look to it and was named "Interline Forwarder".
For those who don't know, that is a person or organization that looks after the logistics of moving freight between modes of transportation - from ships to trucks and so forth.
The background of the name meant nothing I could see in terms of a sailboat but it somehow reflected the personality of the boat very well.
Another name, on THE ugliest boat I ever saw - the closest description I can give is that it looked like a single catamaran hull, upside down. It was a humpbacked, hogged sheer, bright yellow freak named "Zog".