This guy is smart enough to set booby traps for those less-deserving crooks who dare take his share of the treasure he so "manfully" earned. (and by so doing, he helps save the goonies.)
Captain James Hook
Only one hand and this guy still manages to hold his own against a boy who can fly.
Dread Pirate Roberts
Okay, so the original Roberts retired to Patagonia to live like a king, so it's really Westley that I admire, but come on. He sails, climbs the Cliffs of Insanity, fences, beats giants, and outwits evil geniuses. (not to mention coming back to life a couple times.) All this in addition to plunder and mayhem on the high seas, and in a mask, no less? Awesome.
Captain Jack Sparrow
I couldn't leave him out. Why? He's always one step ahead of his enemies (and frequently his friends), managing to confuse others with his bizarre behavior, but then coming out on top so he can "raid, pillage, plunder, and otherwise pilfer [his] weasly black guts out." You'd think that kind of purpose in life would make him the bad guy, but somehow ... it doesn't.
So ... smart, athletic, fashion-savvy, and just plain cool? Yeah, I want to be a pirate. Just have to cure that sea-sickness problem.
"Avast there, mateys! Ye're sailing with Long John Blackbeard Peg-leg Patch-eye Hook!" -Ray Stevens, The Pirate Song