10. Dodgeball (2004)
I know, I know. I'm starting off with a cheat. But the only reason that Dodgeball is this low on the list is that it isn't really about pirates. It's just about one, awesome pirate named Steve played by Wash from Firefly. That's good enough to bump it above most "real" pirate flicks. Garrr!
9. Blackbeard's Ghost (1968)
I've got no objectivity when it comes to Peter Ustinov's Blackbeard trying to help Dean Jones and a bunch of old ladies save an ancient, pirate-themed inn from being destroyed by crooked landlords. This was one of my favorite childhood movies, but it does hold up fairly well. There's lots of goofy slapstick and Ustinov is thoroughly charming. And Disney doesn't spare any expense on the awesome, old, pirate inn.
8. Abbott and Costello Meet Captain Kidd (1952)
Dude, it's Abbott and Costello. That's all you really need to know. And Charles Laughton is surprisingly hilarious reprising his role from the much less fun Captain Kidd. Anyone who can hold his own against Lou Costello deserves some recognition. It's too bad it's not available on DVD.
7. Tie: Disney's Peter Pan (1953)/Peter Pan (2003)
If I really had to pick between the two I'd choose Disney's version because it's awesome and it defines Peter Pan for so many people. But man, you can't ignore Jason Isaacs as Captain Hook. You just can't.
6. Treasure Planet (2002)
I don't care what everyone says about this being the movie that killed traditional animation at Disney for a while. It wasn't because Treasure Planet was bad, it was because Disney had been releasing too much stuff and folks were just getting tired of it. Treasure Planet is actually an awesome, well-designed, faithful adaptation of Treasure Island. Or as faithful as it can be and still be set in outer space. It got a raw deal is all I'm saying.
5. The Phantom (1996)
This might be another cheat, but the Singh Brotherhood are undeniably pirates - and very piratey pirates at that - so I'm counting it (even if it is impossible to find pictures of the pirates online). This is another movie that gets a bum rap by people who have no souls. It's better than every Indiana Jones movie except Raiders of the Lost Ark. I seriously don't get the negative reputation.
4. The Princess Bride (1987)
At last one we can all agree on. Cary Elwes held onto the title of World's Coolest Pirate for a nice, long time and there's no dishonor in having it taken away by Johnny Freakin Depp.
3. Treasure Island (1950)
Classic. Robert Newton's Long John Silver defined the word "pirate" for everyone who came after him.
2. Captain Blood (1935)
Of course, Errol Flynn defined "pirate" for everyone who came before Newton. Newton may be more influential over the popular perception of pirates, but Flynn's a lot more fun (and that's saying something, because Newton is fun). Plus, Flynn gets to smooch Olivia de Haviland.
1. Pirates of the Caribbean trilogy (2003-2007)
They took everything I ever loved about pirates and sea adventures and rolled it all into three awesome films. Sure, it would've been cool if they'd added another hour to At World's End and shown some other stuff I wanted to see, but they more than made up for it, all things considered.