Funniest pirate I came across was in Newcastle, he stopped my AT in a LR gunboat and demanded $10, I said u mean $1 mill, no he said just $10 I need beer money, so I paid and off he went to the nearest bar.
At the other extreme 2 pirates in NB wanted something like 3 mill each, I said you will have to kill me for that, so they did, luckily I had my new Kevlar escape pod (or I would not be telling this story).