The Top 10 Best Pirate Movies

July 17, 2020July 11, 2020 Patrick Sessoms Carey Elwes, Dustin Hoffman, Errol Flynn, islands, muppets, musical, Navy, ocean, pirates, Robbin Williams, sea, ship, steal, survival, swords, swordsmen, thief, thieves, Tim Curry, Tom Hanks

5. Captain Blood

He’ll cut his enemies down and then patch them up again.

What did I just say about Errol Flynn? If it was a pirate movie before the 50s, he was probably the star of it. This time he plays an Irish doctor named Peter Blood, who has a serious issue with England after the King sells him into slavery. With the proper motivation in place, Blood leads a rebellion, seizes control of a Spanish Man-o-War, and sets off to get his plunder on. Of course, being an Errol Flynn flick, Captain Blood has to find a lady to win over before the credits roll, and he sets his sights on the one who bought him in the first place, which is kind of a weird form of revenge in its own. As a former doctor, Captain Blood has a brain on his shoulders and manages to use that to defy the odds as he sets off across the seven seas. Still, I couldn’t help thinking that his actual title should have been Dr. Captain Blood or Captain Blood M.D,.

4. Muppet Treasure Island

There have been a few cinematic adaptations of the classic novel over the years (over 50!). But the one I’m putting on this list of the best pirate movies is the muppet version. Not only does it feature all your favorite muppets from Kermit to Miss Piggy and all the ones in between, but it also has Tim Curry in the role of the notorious Long John Silver, who, surprisingly, is not the founder of the fast seafood food chain. The film follows a group of misfits in a race to find a lost buried treasure before old Long John can get his hands on it and offers plenty of hilarious moments along the way. I can honestly say that Muppet Treasure Island is one of the most enjoyable movies on this list and perfect for a family to enjoy together. So, if you haven’t watched it yet, gather up your little ones and check it out. It’s important to teach kids about pirates at a young age, after all.

3. Hook

The legendary boy who would never grow up went and got himself a job, mortgage, 2.5 kids, and a dog. Living the American dream now, Peter Pan (played by Robin Williams) has all but forgotten Neverland. That is until his old nemesis comes a-knocking. With his children kidnapped, Peter is forced to return to Neverland and confront Captain James Hook (Dustin Hoffman). The thing is that middle age has not been kind to Peter, and he’s got to learn how to do the whole lost boy thing all over again. Time is of the essence as Hook tries to get his, um, hook into Peter’s son and turn him to the dark side (pirates are a lot like Sith Lords I guess). Despite being one of the best pirate movies of all time, I can’t help thinking that it would have been easier if Peter had used the same solution as Captain Phillips…

2. The Princess Bride

All in a day’s work for the Dread Pirate Roberts.

In my opinion, The Princess Bride is one of the greatest films of all time. It’s a magical fairy tale that features “Fencing, fighting, torture, revenge, giants, monsters, chases, escapes, true love, miracles…” and, of course, pirates. Rather, it features one pirate who is crucial to the entire story. Before returning to rescue his true love, Princess Buttercup (Robin Wright), Westly (Carey Elwes) had to learn the skills to pay the bills and was taken under the tutelage of the Dread Pirate Roberts. Whatever Roberts did, it worked out because Westly became one of the greatest swordsmen in movie history and ended up earning the title of the Dread Pirate Roberts when his predecessor retired. Clad all in black with a matching mask (which is apparently terribly comfortable), Westly proved to be the best pirate captain on this list.

1. Pirates of the Caribbean: The Curse of the Black Pearl

While Westly might be arguably a better captain than Jack Sparrow, The Princess Bride is severely lacking in the “pirate department” when compared to Pirates of the Caribbean. Besides, as much as I love The Princess Bride, I can’t argue that Pirates isn’t a worldwide box office sensation. Depp plays the infamous Captain Jack Sparrow, an unconventional scoundrel with a bad reputation among The Royal Navy and pirates alike. When a ship of immortal undead pirates shows up looking for trouble, it turns out an unconventional scoundrel is exactly what’s needed. Now, the sequels in the franchise weren’t much to write home about, but the original is definitely worthy of the top spot on this list of pirate movies. The upcoming sequel featuring Margot Robbie might mutiny and steal it though. We’ll just have to wait and see.

Honorable Mention: The Goonies

This is what happens when you leave your child without adult supervision all day.

HEY YOU GUYS! Sorry, we couldn’t resist. While there might not be any actual pirates in this movie, we get to see lots of skeletons and a pretty sweet pirate ship in this classic 80s flick. Besides, any excuse to bring up The Goonies is fine by me. Besides, it just gives me a chance to say “One-Eyed” Willie without getting a bunch of dirty looks (if you don’t get the reference, you clearly need to rewatch this incredible film).

Animated Shout-Out: Treasure Planet

Second star to the right and straight on till- Wait, wrong movie.

I know I banned space pirates early on in this list, but Treasure Planet is a solid candidate for exception to that rule. It’s a retelling of Treasure Island set in the far future where people, robots, and aliens use techno-ships to sail the seven… Spaces? Any way, Treasure Planet has beautiful animation featuring some amazing design choices that have made it a cult favorite among artists in particular. Because of that, I’m giving this animated flick a shout out.

Dishonorable Mention: Waterworld

This is why we need to be concerned about the ice caps melting.

There’s not much of an argument for the merits of Kevin Costner’s epic flop especially since it featured a mutant Costner drinking his own pee and a Pirate King (Dennis Hopper) with an armada of jet skis. Waterworld is one of the most legendary disasters in cinema history and since it does feature pirates in it, I thought I should shame it on this list. The only good thing is it can be used as a perfect example for why we should be worried about global warming, since none of us want to live in a world like this.

For my money, those are the best 10 pirate movies of all time. There are plenty of other great ones out there, and if you think this list is missing any of them, leave me a comment below. As always, I’ll be updating this list as new pirate movies make their way to the big screen. So, be sure to check back from time to time in order to see how the rankings might change!

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