What's the greatest pirate movie of all time?

The Princess Bride

What kind of pirate?

Pirates of silicon valley is pretty good covering the apple/Microsoft early days

Otherwise goonies is a classic

Yellow Beard

Muppets treasure island

Ice Pirates

Cutthroat Island

Serenity or Captain Phillips, although I don't think that's what you're looking for.

https://youtu.be/U744X4O6gXE?feature=shared