Night Shade Books will be releasing Jeff & Ann Vandermeer's Fast Ships, Black Sails so I thought to highlight some pirates from my own personal history. Alas, as a kid, I wasn't really reading books but playing video games and watching anime so... (feel free to add your favorite pirates in the comments section)
1) The Lost Vikings - Arguably one of the first pirates were the vikings. Loot, pillage, and plunder! In the case of this addictive puzzle game created by the then-unknown company called Silicon & Synapse (how times would change as they're currently one of the most popular gaming companies of all time, Blizzard), you controlled one of three characters, each with a unique special ability (Olaf for example has a shield which can be used as a hang-glider or more typically, to act as a stepping stone for other characters.) Not exactly the video game that first comes to mind when you're talking about 16-bit consoles but this was actually an enjoyable game for the Lemmings crowd without being too derivative.
2) Space Pirate Captain Harlock - Whoever said pirates stuck to the Seven Seas? Space Pirate Captain Harlock is one of the more iconic manga/anime characters, especially for the older otaku generation. Numerous sequels and cameos down the line, Harlock is still an enduring franchise.
3) The Pirates of Dark Water - One of the better US cartoons produced during the early 90s, The Pirates of Dark Water combined great animation with competent storytelling wherein the previous episodes actually mattered. It was edgy for its time and didn't feature a Caucasian protagonist. Interesting characters include flying monkeys and a female pirate geomancer. Unfortunately, the high production values took its toll and the series remains unfinished.
4) One Piece - One of my current favorite manga series, the protagonists of One Piece best captures the spirit of pirates with its underlying philosophy of mastering one's own fate and being ready to lay one's life on the line. Aside from the wacky fantastical elements (Luffy, the pirate captain, is made of rubber for example), the super-powered characters are limited by the fact that they can't swim (a trade-off for their special abilities) which makes the pirate venture all the more interesting. Overall it reconciles heroism while still being a bad-ass pirate.
5) The Secret of Monkey Island - Another old-school video game, The Secret of Monkey Island was one of the games that used the SCUMM Engine, allowing players to interact in-game beyond the attack/hit/kill mechanic. Players participated in an interactive pirate-y adventure. The fact that the creator was inspired by Tim Powers's On Stranger Tides is a bonus.
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