A pirate is not a pirate is not a pirate. The pirate has been a long-standing staple of a lot of fiction, and as such has many different interpretations and styles, mostly stretching in a spectrum from realism and brutality to stylish fiction. In reality, of course, most pirates were brutal criminals who lived short and horrifying lives. (Very few pirates in reality lived to an old age; disease and bullets got most of ‘em.) But on the other end, we adore the romantic pirate of film and legend.
There are probably three distinct “types” of pirate we can really pin down, but it is a spectrum. A pirate in the middle may stretch toward either end, a pirate at either end may stretch to the middle. Every character is unique.
The Brutal Buccaneer: Driven by greed and sadism, the brutal buccaneer is the terror of the sea. He doesn’t fly the skull and crossbones because that would give his enemies too much chance to spot him. Instead, he flies the colors of whichever nation he’s closest to, in the hopes of lulling his opponents into passing close by. He keeps a loose reign on his crew in pillaging – And as such, being raided by him is a nightmarish experience characterised by sadistic violence, rape and murder. (This is actually a deliberate strategy, sadly enough, to keep morale high amongst his crew.) However, he may be quite calculating and brilliant in battle; nothing in the job description requires him to be stupid as well as brutal. The best real life pirates were cunning and sneaky. Examples: Blackbeard and pretty much every real life pirate you can name, Captain Barbosa.
Role-playing tips: The Brutal Buccaneer is a hard character to play for most people because it thrives on a basic amorality – The vast majority of people, to you, are there to be robbed in as many ways as you can think of. But if you want to give your character a few more interesting shades of grey (and we sincerely hope you do) then you should probably think in tribalistic terms with this character. These pirates could genuinely be very loyal to their men, could sincerely care for them and try to ‘do right’ by them. They knew all too well the possibility of mutiny and worked hard to avoid it, but these efforts tended to breed some genuine feeling as well. Decide early on whom your ‘tribe’ is. Probably your faction is too big, but your guild may be a good definition. Perhaps there’s a small clutch of friends in your circle. But anyone else is fair game – For anything.
The Cavalier Corsair: There’s only one person in this world who will look out for you, and that person’s been looking out for this guy with gusto for as long as he can remember. He’s a loner, probably owning a small ship at best (assuming he owns a ship) and finding it difficult to keep a steady crew. Like the Brutal Buccaneer, he’s a wanted man on the high seas, but unlike him, he’s not quite the subject of so many terrified rumors. The crew he does have he keeps a tight, powerful grip on, preventing them from the worst excesses. There’s simply no profit in uncontrolled savagery. And in the end, that’s the notion that keeps him going. Profit. As such, he generally seems fairly decent most of the time, he’s certainly understandable if nothing else. But that’s why it’s so much more shocking when he does perpetrate some act of unimaginable violence. While he’s happy if people misunderstand, he is more than capable of murder and more – But only if there’s a profit involved. Examples: Han Solo, Captain Jack Sparrow (and to some degree, Elizabeth Swan.)
Role-playing tips: I’m not a hundred-percent sure why, but this is the best role of the three for female pirates. There’s no reason a female pirate couldn’t be a Brutal Buccaneer, but we seem to have trouble imagining a woman that bloodthirsty. (As it was, though, there were a few real female pirates and, yes, they were that bloodthirsty.) And a woman couldn’t certainly be a romantic type as discussed below, but it somehow lacks edge. This is the perfect balance, and it really fits that old notion that “the female of the species is always deadlier than the male”.
Plus, women have this tendency to be more charming than men, and affecting a certain roguish charm is what this type of pirate is all about. Look at the examples – There are probably no two characters who more sum up the contemporary appeal of the pirate as those two. Since the dramatic impact of this character comes from being someone who you know you can’t trust, but nonetheless want to like, you need to manage to affect both a basic unreliability and an insouciant allure. Pet the Dog whenever you get the chance, be nice as often as possible while at the same time looking for chances to do some truly disreputable things for money. (This might be a fun character to fictionally ‘ninja’ loot with; ask for permission from everyone first, but then claim an object found in a dungeon and tell the party that only you saw it. Later, when you use it, they can explode at you for stealing it.)
The Polite Privateer: When you became a pirate, one gets the feeling you did it mostly to impress women. Certainly, you don’t seem to have much interest in actually hurting people or stealing things. If you’ve ever raided a ship, it’s almost certain that you didn’t kill a single sailor on either side in the process. You wouldn’t dream of letting your crew harm a woman, in fact, you’re likely to apologise to one for the rude shock. And that’s if you’ve done such things, you’re just as likely to have never done anything of the sort, and be something of a greenhorn to the whole piracy thing. You can use a sword well, and you do enjoy a grog, but you know, the whole villainy part of the equation just doesn’t appeal. Probably you make more money from smuggling than banditry, from non-violent crime than any other sort. Meanwhile, you’re either rakishly devilish, or naively charming. Examples: Errol Flynn’s many characters, The Dread Pirate Roberts/Westley from the Princess Bride, and Guybrush Threepwood.
Role-playing tips: Really, this guy isn’t really even a pirate. But he digs the image. They key here is to somehow project the required sense of danger and mystery when really, you’re not dangerous, and furthermore, you’re hanging around with the same guys all the time, destroying any sense of mystery too. Really, the key here is to swashbuckle. Practice your quippy one-liners whenever you’re not playing the game. You might even want to have a macro that announces you’ve clubbed your target over the head, knocking them unconscious for when you kill an enemy, especially a female enemy. Be either casually chivalrous or stutter like a teenager around women, depending upon which way you want to play it, but be sure to come to their aid pronto when they’re in trouble. Basically, be a nice guy trying not to seem a nice guy, and either succeed or fail in that endeavor as you find more amusing.