Who wouldn't want to be a pirate. You get to go where you want, take what you want, shoot what you want and be a grungy layabout. Then, if you're a pirate, you instantly get tons of street cred. Pirates are the curs of the sea, and they don't take any lip from anyone. Plus, pirate = rum, and lots of it.
Of course, there are downsides to being a pirate. There's voodoo, being chased by the East India Trading Company, getting all manner of fish eyeing you up for food, and the constant threat of sea madness. Although, those things do all have a certain romantic attraction to them as well.
It's something to debate. But when it comes right down to it, I say Pirate...yes!