I would have to say go with Jack, but not just because he's hot. He's got the whole pirate, mystery thing going for him. Although if if I had lived in that time I would have probabley already been a pirate  .
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England forever! And Scotland for a wee bit longer!!
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Jack Sparrow: The only rules that really matter are these: what a man can do and what a man can't do. For instance, you can accept that your father was a pirate and a good man or you can't. But pirate is in your blood, boy, so you'll have to square with that some day. And me, for example, I can let you drown, but I can't bring this ship into Tortuga all by me onesies, savvy? So, can you sail under the command of a pirate, or can you not?
-Pirates of the Caribbean: Curse of the Black Pearl-
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