Pirates of the Caribbean: The Curse of the Black Pearl. As with The Matrix it’s a pity that they never made any sequels.
If you like a pirate {and what right thinking person doesn’t?) then you should click this link to the Internet Archive to watch Captain Kidd with Charles Laughton having any amount of fun as magnificent bastard William Kidd.
People have said the pirates of the Caribbean trilogy. I want to specifically call out the first movie. It was a pure love letter to old pirate movies, and you get to see Jack sparrow actually be clever and serious, before he was flanderized into funny dirt jar man. The two sequels are fun, but each one took a notable drop in character writing for cheap gags.
It’s basically the same thing that happened to Homer Simpson. The original did dumb things but never intended for things to fail or to be evil. Of course it is easier to write cheap gags if you throw all of that out of the window.
My first thought was Pirate Latitudes, a book written by Michael Chricton, author of Jurassic Park. Never saw a movie adaptation but he is the Stephen King of sci fi, so maybe someday. Also my favorite book of his, despite what others may say