The subject matter of this album includes(but is not limited to) being a drunken sailor, theft, digging for gold, appreciation for the female form, and attacking Santa Claus.
I'm wondering whether this is due to someone seeing too many pirate movies, if this guy is a follower of the Flying Spaghetti Monster, if his sense of humor is like mine (hmmmm....rap and pirates, these are two things that shouldn't go together under any circumstances - let's see what happens), if he's intentionally drawin comparisons between "gangstas" and pirates (two types of criminal that get romanticized for no good reason), or some combination of all of the above.
Ah, fuck it, why am I analyzing something that's funny. It's funny, let's leave it at that.