The 25 Greatest Pirate Movies Of All Time

The marketing has been…let’s call it unclear. Is Pirates of the Caribbean: Dead Men Tell No Tales the last movie in the franchise, or the last movie for Captain Jack, or the last movie until they decide they want to make another movie because the Pirates of the Caribbean title is basically a license to print copious amounts of cash? Who know and frankly, at some point, do any of us really care? I’m not sure I do, but the release of Captain Jack’s latest adventure is a perfect excuse to release The 25 Greatest Pirate Movies Of All Time list (actually an update of the list I did originally in 2012, but for fun let’s pretend like this is a totally new and original idea).

…and no, the list isn’t all Johnny Depp and Errol Flynn…

Generally, the trick to making a movie list is making the hard cuts. There are too many great action movies, so making a X number of greatest action movies list requires you to decide between, say, First Blood and Death Wish (First Blood is the answer). Both good movies, both “deserve” to make the list, but you’ve got to make the cut-off somewhere. Hollywood has a long history with pirate movies, starting in 1908 with The Pirate’s Gold directed by D.W. Griffith himself (I know, that will only mean something to movie nerds), but it turns out most of them suck. Go hop around the inter-webs and check out some other “best Pirate movies” lists, you will find that Pirates (2005), an adult film starring Jesse Jane and Carmen Luvana, pops up frequently and no one is putting it on their lists ironically (quick aside, when I first did this list in 2012 and pointed out that this adult film had cracked many a pirate list I suddenly got followed by a handful of the performers from that film on Twitter, thankfully my wife found it funny and not suspicious). I think we can all agree that if porn can match the highest quality of a genre, maybe the depth of quality in that genre can be questioned. Having said that, I found 25 that absolutely belong. Some are stupid, because pirate movies have a tendency to ere toward stupid, but damn it if they’re not fun.

25. Cutthroat Island (1995)
 The Renny Harlin/Geena Davis collaborati

on is widely considered one of the biggest bombs of the 90’s. Frank Langella’s Dawg (the film’s bad guy) may be the most over-acted character in movie history and I still don’t know what accent Geena Davis is going for in this movie (kind of, vaguely, a little bit, British-esque). Renny Harlin, like Michael Bay and James Cameron, makes cool looking movies, and this is no exception. Its obvious and stupid and the acting is comically bad, but it is pretty and that counts for something.

24. The Ice Pirates (1984) – Purposely stupid this is a film with a couple of interesting tidbits. First, it has a young Angelica Houston and Ron Perlman in it. Second, you get to see Oakland Raider John Matuszak (often considered the craziest person to ever play in the NFL) in a major role. Third, Robert Urich gets to play for laughs (sure we laughed at SWAT and Spencer For Hire and Vegas but I don’t think we were supposed to). What more do you want from a movie about trying to steal ice?

23. The Pirates of Penzance (1983) – Kevin Kline as the singing, dancing Pirate King. Linda Ronstadt as the young Mabel (I think she was 40 when they made this, making her casting kind of funny). Angela Lansbury playing sexy (ish) for the last time. It takes Gilbert and Sullivan’s comic operetta and mixes some parts of their other works in (who knew their pirates wasn’t enough?). None of this description sounds that good, but somehow it all works.

22. Pirates! Band of Misfits (2012) – This movie was the inspiration for my first pirate movie list. After the trailer I was so excited it compelled me to research pirate movies … yes, I am aware that sounds weird. Anyway, Pirates! Band of Misfits did not live up to my absurdly high expectations, but that is the problem with high expectations, they tend to let you down. In viewing since, however, I have grown to like it more and more (as is often true of the Aardman Animation Studios movies like Chicken Run and Wallace and Gromit and Shaun of the Sheep). It is absurd, Hugh Grant is perfect in the voice role of the captain and whole thing is kind of delight (see previous statement about Aardman Animation Studios movies).

21. Pirate of the Caribbean: At World’s End (2007) – I think this movie had two things working against it. First, that its predecessor, Dead Man’s Chest, was a huge disappointment (it just lacked the magic of Black Pearl and turned a lot of people off). Second, it needed some editing, which is to say it was too long. Still, it has a lot of fun scenes, a lot of amusing maneuvering by Captain Jack and some really cool battles and sword fight sequences.

20. Treasure Planet (2002) – Disney’s animated version of treasure island set in space. I read someone who suggested that it was the failure of this movie (budget near $150 million with gross ending around $50 million) that convinced Disney to buy Pixar. Visually this is one of the better animated features you will ever see and the story is a classic tale that is adapted smartly. It may not be the best Treasure Island movie ever, but it is still pretty good.

19. Swiss Family Robinson (1960) – I  put this next to Treasure Island because they are two classic “I loved it when I was a kid” movies that maybe I can’t rate entirely accurately. Still, this is an unquestioned classic and the first of the “people who get stranded on islands and are somehow able to live and eat like kings while they are there” shows that may not be entirely accurate (clearly Tom Hanks is an idiot since he lost all that weight in Castaway and had to live in a cave, he wasn’t even able to befriend a monkey!).

18. Treasure Island (1950) – Young Jim Hawkins is caught up with the pirate Long John Silver in search of the buried treasure of buccaneer Captain Flint. This was THE Treasure Island for me — more than the book, more than any other adaptation. When I picture Long John Silver I picture Robert Newton’s Long John Silver. Frankly, when I picture a pirate I picture Robert Newton’s Long John Silver (as I am sure many people between the ages of 40 and 60 do).

17. Pirates (1986) – Walter Mathau as a crusty evil pirate in a Roman Polanski movie that took something like 12 years to finish because Polanski was running away from the warrant placed on him in the United States. Its a good movie, although few have seen it. Maybe Polanski should have put a little more merriment or a wink to the audience in there that would lighten the film a a wee bit, but it is still fun to watch Mathau play massively against type and it is perhaps the only self-serious pirate movie on the list (no Keith Richards impersonations here).

16. Yellowbeard (1983) – But, if you really want to watch a pirate movie made in the early to mid 1980’s you should check out Yellowbeard. An Australian paper described this movie as having “every funny person making movies today in one movie” and they were pretty close to right. Cheech and Chong at their height. Peter Boyle, Marty Feldman and Madeline Kahn (on the heels of their Mel Brooks collaborations). And while it is not officially a Python film it was co-written by and starring Graham Chapman and has cameos by Eric Idle and John Cleese. I’m not going to lie, this movie isn’t as good as all of that would make you hope it would be (it even has James Mason in it), but it still has some really funny parts and is worth a late night viewing.

15. The Island (1980) – Apparently I’m on a 1980’s kick, my wasted high school and college years are making an impact. Michael Cain (a reporter) takes his son to the caribbean as he investigates missing ships in Peter Benchley’s story (he wrote Jaws and The Deep among other novels). Not surprisingly it turns out that modern day pirates are behind the disappearances. Its kind of funny how pirates of yore are anti-heroes and modes day pirates are thieves. Of course all pirates are thieves, by definition. But we like Captain Jack and believe me, you will not like David Warner’s John David Nau.

14. Peter Pan (1953) – I think this era of Disney is to me what Pixar will be to my son. When I ask him to name his favorite Pixar movie he can name one (although it is often the last one he saw), but when I start to rattle off the other Pixar movies he is always like “ooh, that one was really good too” and “oh yeah, I love that one” until you realize he likes all of them. That is how I am with Disney’s animated movies from 1937 (when Snow White came out) until Winnie the Pooh in the mid 70’s (go look at the list sometime, other than Make Mine Music and The Adventures of Ichabod and Mr. Toad they are all considered classics). Peter Pan may not be anywhere near my favorite, but that doesn’t mean I still don’t look at it as a classic.

13. Captain Phillips (2013) – As to prove my point about pirates of myth and pirates of today (see #15 The Island) we get the true story of Somali pirates hijacking a U.S. cargo ship in 2009. Hanks has had a run of movies (Captain Phillips, Bridge of Spies, Sully) that are based on true stores and are all really made well, he’s great, generally some terrific supporting role performances (Mark Rylance actually winning the Oscar for Bridge of Spies in 2016 and a nomination for Barkhad Abdi for Captain Phillips), but none of them have quiet captured audiences the way you’d think they would (or maybe just the way Hanks movies always seemed to in the 1990’s). Obviously, Captain Phillips is still a really good movie and absolutely worth a watch if you haven’t caught it before, but is it great? Is it a classic? Maybe not quite.

12. Serenity (2005) – Let’s be clear, we are just talking about the movie. Firefly, the TV series, would be a top 1 or 2 pirate movie of all time, no question, hands down. But, you know, its not a movie. Serenity is really good, an interesting expansion of the world and a fitting next chapter for the main characters, but I don’t think even the most die hard of die hard Firefly fans think the movie matched the series (maybe the expanded budget and the ability to expand the universe took the movie away from the pirate sensibilities that made the show so fun, but I’m writing a pirate list so of course that’s where my mind goes). One of the things that is terrific about both the film and the series is that, while most pirate tales focus on the captain as being the epitome of what a pirate should be, the entire crew here represents all the sides and shades of what it would mean to be a pirate in their universe; the good, the bad, the moral justification and the moral ramifications, it is all in there and wrapped up in a super fun package. Look, if you haven’t seen the series watch it first and if you have seen the series, well then you have seen the movie and I don’t need to explain anymore. There is a very good reason when you look up cult classic in the dictionary a picture of the crew of the serenity is what comes up.

11. Blackbeard’s Ghost (1968) – As I said, I loved Disney’s animated run that lasted 30 years (see Peter Pan at #14), but I may love their live action comedy of the 60’s and 70’s even more. The Shaggy Dog, The Absent Minded Professor, the Herbie movies, The Parent Trap, Kurt Russell’s twin bill of The Computer Who Wore Tennis Shoes and The World’s Strongest ManFlubber and more. When I was a kid this may have been my favorite of all of them. Peter Ustinov is having the time of his life in this goofy (in all the right ways) movie about a pirate ghost and Dean Jones is as ever the perfect straight man. Hard to find now, but if you can it is definitely worth it.

10. Waterworld (1995) Waterworld is absolutely a “remote stopper”. You know, the kind of movie that you almost always stop on when you are flipping through the channels trying to find something to watch. My favorite story about it is that the writers first brought the movie to Roger Corman, the king of B movies, who read it and said he couldn’t make it because it would take $10 million to make and it could never make that money back. Of course, Waterworld famously cost something like $200 million to make, with sets sinking and hurricanes delaying production (see my earlier note about the cost of making movies on water) and ended up being the beginning of the end for Costner being the biggest movie star in the world. Its silly and over the top, but it is funny and a good pirate movie.

9. The Buccaneer (1958) Now we are getting to some real pirate classics. Yul Brenner as Jean Lafitte trying to decide if he should help protect New Orleans from British invasion or if he should side with the British, who will likely win the day. Anthony Quinn directed this movie and is a remake of a 1938 version directed by Cecil B. Demille (who produced this version). In the end this is perhaps more of a war story than a classic pirate story, but Yul Brenner is great and Charlton Heston has a nice turn in a supporting role as Andrew Jackson. While some claim this to be based on a true story (Lafitte is/was a real person) I think to say this was highly fictionalized is an understatement if anything.

8. Star Wars Episode IV: A New Hope (1977) – I know what you are thinking,”CHEATER! You should have put the porn flick on this list!” Ok, maybe not the second part, but I can hearing you screaming that first bit, but here’s the thing … Han Solo is a pirate AND the Millennium Falcon is a pirate ship. Obviously, Star Wars is not a purely pirate movie (just like how obviously if it were being judged just based on being a movie it is #1 with a bullet on this list) but it belongs here… Honestly… I did not simply include it because I wanted to find more good movies to put on this list and I am deeply offended that anyone would say otherwise… Seriously! HE’S A PIRATE and HAN SHOT FIRST!

7. The Goonies (1985) – Who doesn’t love The Goonies? Its funny, exciting, holds up spectacularly well and is really touching. Kids looking for “One-Eyed” Willy’s treasure in a last ditch attempt to save their homes and the friendships they have made. Just great stuff. And you get a young Josh Brolin rockin’ the shorts over the sweat pants look, so what’s not to love?

6. The Sea Hawk (1940) – While Johnny Depp may represent pirates to people under 30 for anyone over 40 Errol Flynn was the hollywood personification of the swashbuckling pirate. Of course these pirates really aren’t pirates — they are Robin Hood of the seas. Outwardly bad, but really motivated by the noblest of motivations. This is also one of those funny movies where the least swarthy people in the world are cast to play Spanish (Brenda Marshall and Claude Rains). But I am poking holes where none should be poked. This is old time hollywood action at its best.

 5. The Crimson Pirate (1952) – I loved this movie when I was a kid and it used to play a lot on Saturdays and it was a part of ABC’s afternoon movies rotation (along with a ton of classics like The Great Escape and The Raven). Then, when cable came out and I got older it kind of became a lost movie. That sucked for me because for some reason I never learned the name of it. For years I would ask people “hey, do you know that pirate movie with the one guy who’s like the captain who does all the gymnastics stuff and then he has a mute first mate and they do pirate stuff and its really funny?” Turns out it was Burt Lancaster playing the pirate doing the gymnastics stuff. This is a movie played 100% for laughs and it gets them. I finally found it again when I was in my 20’s and I am thrilled to say, for me at least, it more than holds up. Now its considered a bit of a classic and isn’t impossible to find, so if you see it watch it and thank me later.

4. Captain Blood (1935) – This is really is Errol Flynn doing Robin Hood as a pirate, and doing it really well. Often named as the greatest pirate movie of all time this is about a doctor who is falsely convicted and imprisoned then sold as a slave. When Spanish ships attack the city he and his slave friends rebel, free themselves and become pirates. Olivia de Havilland plays the love interest which made this akin to a Brad Pitt/Angelina Jolie movie (not because of personal relationships but because of the relative fame of the two leads) in its day. This has been called the birthplace of hollywood swashbuckling and I promise If you like Errol Flynn’s The Adventures of Robin Hood, you will love Captain Blood.

3. The Princess Bride (1987) – You know what I find fascinating about The Princess Bride? How often I end up putting it on lists. It was part of my recent top 50 book to film adaptations list. I have had it on romantic comedy lists and best of the 80’s lists and now on a pirate list – and it deserves to be on all of them. It is that unique film that just works on nearly every level. The sword fighting is terrific, the comedy is wonderful and the parts that are meant to be touching really move you. Besides, I wouldn’t want the dread pirate Roberts to come get me, he never leaves any survivors. Here is the sword fight between Inigo Montoya and The Dread Pirate Roberts:

2. Pirates of the Caribbean: The Curse of the Black Pearl (2003) – Try to remember how surprised you were 9 years ago. Johnny Depp carrying a movie? A pirate movie based on a ride at Disneyland? Who saw this coming? Love or hate the sequels, Captain Jack Sparrow has already secured his place on the list of the greatest movie characters of all time. This movie is funny, unexpected, charming, exciting (even scary if you are young enough) and proved that pirate movies weren’t dead after all. Frankly, to me this was an easy choice.

1. Time Bandits (1981) – Let me be upfront, I LOVE Terry Gilliam movies (here’s the list of his films on IMDB). Let me be honest about something else, not everyone loves Terry Gilliam movies (I KNOW! That’s Insane!). Also, I love Monty Python, and while Time Bandits isn’t officially a Monty Python movie, it was written by two former Python members (Gilliam and Michael Palin) and it stars John Cleese as Robin Hood (among other people, notably Sean Connery). Here’s the thing, not everyone love Monty Python (*#$@!%#!). So, if you don’t like strange, cool movies with visual pallets that come alive and a story that will make you examine the child inside of you while at the same time being just fun and funny, then this is not the movie for you. Did I phrase that so you would feel a little bit bad if you aren’t all in on Time Bandits? Obviously, because Time Bandits is awesome!

Of course, I could be wrong. After all, what d I know, I’m fat?