i would have to say that by far the best pirate was barthalomew roberts, of wales. otherwise known as black bart.
the other querstion that i often ponder is weather i would have rather been a pirate in the carribbean, based out of somewhere like antigua or jamaca, or weather the indian ocean pirate base of madagascar is what i would prefer. you also have to question what time period would have been best for piracy. i hold with the common view that the early 18th centrury (1719 or thereabouts) would have been prime. anytime before that, and you were basically a mercenary, or a privateer. still connected to a state government in all likleyhood.  after the close fo the war of spanish secession, however, is when pirates really became their own entity, running up the black colors, and declaring war on all the world. that is really why the time period from 1710-1725 is known as the golden age of piracy.
another aspect of piracy that i like is the vigilate nature of it. i mean, what vindication they must have felt as they boarded prize vessels, and took the fate of the captain in their hands, according to the testimonies of the captured crew.
yes, it would have been a pirates life for me.
Mercy's eyes are blue
When she places them in front of you
Nothing holds a roman candle to
The solemn warmth you feel inside