The Sea Hawk

1940 version directed by Michael Cutiz and starring Erroll Flynn, Brenda Marshall, Claude Raines, Donald Crisp, and Alan Hale.

Rousing pirate film with just the right mix: swashbuckling adventure, ship battles, swordplay, and romance.

Curtiz and Flynn were almost always a good mix and this is one to be enjoyed me hearties.

http://www.imdb.com/title/tt0033028/

The Crimson Pirate

I've heared that Burt Lancaster was a circus performer before making it as an actor. If that's true, the evidence is apparant in his athletic film roles.

Yes...another pirate movie! ARRRGH! But I love 'em. Bucle me a swash anytime.

This 1952 film stars Lancaster, Nick Cravat, and Christopher Lee and was directed by Robert Siodmak. And I'll tell you, I think it holds up well against any other pirate movie for thrills, adventure, humor, and personality.

Suitable for any age, this one's fun. Put on an eyepatch and include it in your pirate marathon.
http://www.imdb.com/title/tt0044517/

Captain Blood

Yo ho ho...it's the Pirate's life for me!

Yes, i loved Johhny Depp as Captain Jack Sparrow. But when I think of pirate movies, the first one that comes to mind is the one I have loved since my childhood: Captain Blood.

Made in 1935 and directed by Michael Curtiz, it stars Basil Rathbone, Olivia de Haviland, and Errol Flynn in the film that not only made him an action star but gave him the vehicle to set the bar pretty high for swashbuckers. The Adventures of Robin Hood, perhaps his most notable role, didn't come along for another three years.

Flynn plays Peter Blood, an Irishman and a doctor. Being non-political, he treats an enemy of the crown and is arrested for his compassionate act. Shipped off to the West Idies, he is sold into slavery where he is bought by de Haviland. Becoming a pirate, he teams up with Basil Rathbone for a short time, but goes off on his own to win battles, his freedom, and the heart of his true love.

Look for great swordplay (Rathbone was an expert and actually taught many stars to fence), rousing battles at sea, broadside, boardings, and romance. This is a great action-adventure even after all these decades.

Skip the colorized version and stick to the original in glorious back and white.
http://www.imdb.com/title/tt0026174/