If I'm feeling like a black and blue steak, I've found that ordering "Pittsburgh" gets more mileage than black and blue.
I've found some bartenders give me an odd look when I order a manhattan: "Knob Creek Manhattan, straight up, half and half, extra bitters". Half and half refers to half sweet, half dry vermouth, which is my personal taste for a manhattan.
I get a fair amount of odd looks in the US when I order fries with mayo. I don't know why, I kinda figured that people had seen mayo on fries by now...
Cheers,
-Andrew