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What is the best thing about pirate movies? If you answered being able to make jokes about plundering booty then you are very juvenile. And also correct. Another great thing about pirate movies is that a little part inside of everyone wants to live a pirate’s life. The swashbuckling ways of the sea make for grand adventures, and there is no comedic relief quite like that of a goofy drunk pirate. When you throw finding buried treasure into the equation it becomes a no-brainer that a pirate’s life is the life for me. Just for the record, those Somalians aren’t real pirates. Only bona fide Pirates like Captain Jack Sparrow are included on this list.

Pirates of the Caribbean: The Curse of the Black Pearl


Speaking of Captain Jack Sparrow, Johnny Depp reminded us how awesome being a pirate could be. While Captain Jack Sparrow was a big part of what made Pirates of the Caribbean amazing, it was also the great story. Once you mix in a haunted ship, a skeletal crew, and a flamboyant pirate captain, the resulting movie is sure to entertain all audiences. The fact that Keira Knightley wears a corset throughout a good portion of the movie just makes it that much better.

Peter Pan


Captain Hook is one of the most memorable pirates of all time. While most of us would prefer being one of the Lost Boys over Captain Hook, he was a very entertaining figure. His interactions with First Mate Mr. Smee are hilarious, but even funnier are Captain Hook’s reactions whenever the crocodile who ate his hand comes near. The tick-tocks of the alarm clock in the crocodile’s stomach are as terrifying to Captain Hook as the Jaws music is to the rest of us.

Treasure Island


Treasure Island is the original pirate story and features the infamous pirate Long John Silver. What made Treasure Island such an enjoyable movie was the fact that the main character was just a kid. It doesn’t get much more relatable than that. Young Jim Hawkins joins up with Long John Silver’s crew of swarthy pirates, and initially everything is hunky dory. Little Hawkins soon learns that being a pirate isn’t all eyepatches and peg legs, and has to deal with the ruthlessness of Long John Silver. This is true adventure on the high seas.

Captain Blood


Captain Blood is an awesome pirate movie for several reasons. First off, the movie is called Captain Blood. That is freaking awesome. Second, Captain Blood is played by Errol Flynn, more widely known as Robin Hood. This casting choice was perfect, as Captain Blood was essentially a pirate version of Robin Hood. Some folks don’t like their pirates to have morals, but it worked in this case Captain Blood remained a bad ass. Even though it was made in 1935, Captain Blood remains entertaining today.

Pirates of the Caribbean: Dead Man’s Chest


The return of Captain Jack Sparrow wasn’t as good as his debut, but it was still a very entertaining movie. Much of this was because Keira Knightley was just as hot as ever, and Johnny Depp was just as eccentric. I guess Orlando Bloom was pretty good too. The story just wasn’t as good as The Curse of the Black Pearl. Of course that can be said about 4 out of the 5 movies on this list. In case you had forgotten, haunted ship + zombie pirates + Keira Knightley cleavage = AWESOME. That is just simple math. Still, Dead Man’s Chest is quite a good movie in its own right.

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Posted by Jordan On September - 2 - 2010

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