The movies have always enjoyed showing a sympathetic view of pirates, although before CGI it was really hard and expensive to do sea movies. Further, the movies have had to tone down the violence, scuzziness, rapine, and general bullying of the pirates---not to mention their weirdness. George MacDonald Fraser (of Flashman fame) in his 1988 tour de force The Hollywood History of the World, wrote:
At first glance, Hollywood and pirates would seem to be made for each other, but in fact they are not.... there is the plain fact that pirates---the real pirates of history---the Blackbeards and Morgans and Kidds and Calico Jacks---are too bizarre, too larger-than-life, too unreal for even the cinema. That they were real is irrelevant; their truth is too strange for fiction, and pantomime and Peter Pan have turned the grim reality into a comic figure which usually defies attempts to fashion it for conventional drama, or even melodrama.Since he wrote we've had Jack Sparrow and his salty brethren, but such cartoony pirates are hardly different from Captain Hook. Ah, but they all long for the freedom of the Seven Seas.
The open sea has long been a symbol of freedom, but we know that actually being on the open sea requires a lot of discipline. It's freaking dangerous out there. So merchant sailors and navies have always had a reputation for strict discipline. Ah, but pirates! They were like democracy on the high seas, right? With compacts and contracts and settling things like men when necessary.
Well, maybe not so much. The thing about lawlessness is that it usually gets filled with something, and it's not usually something friendly. But worse, the pirates were not living the life that's free; they were living the life of a parasite, sucking life from their victims. Without the suckers running honest sailing ships there could be no pirates.
The people who started this holiday are well aware of all this, and know that their day is not focused on historical pirates, but fictional and hysterical pirates, all in good fun. And I think you should don your piratey apparel and go celebrate. Have some grog, sign up with the Dread Pirate Cruller, get your pirate name (mine is "Monkey Mate" Bob Barbossa), and annoy the bilge out of your coworkers.
But think about this: Next year, let's gear up to celebrate a real American hero, not a bunch of jerk pirates like the ones who were the victims of America's first naval butt-whupping. I'm talking about a guy with as distinctive a speech pattern as any pirate, a guy who exemplifies pluck and fellowship, but one who only ever engages in cartoon violence. Yes, folks, remember: June 2, 2015 is the Second Annual Talk Like Slip Mahoney Day. Mark your calendars! (Sorry: YER calendars!)