The 25 Greatest Pirate Movies Of All Time


and no, it isn’t all Johnny Depp and Errol Flynn.
If you have been reading this site for the last few months you have no doubt noticed that one of the movies I am most excited about in 2012 is opening this weekend — The Pirates – Band of Misfits. I think it looks hysterically funny and will be just the right movie for me and my 8 year old son to see and enjoy. With its release mere days away I figured what better time than to do a list of the greatest pirate movies of all time. That should be fun a relatively easy to come up with, right? Well, it turns out it was definitely fun, but not all that easy.
Hollywood has a long history with pirate movies to be sure, it just so happens that most of them stink. We forget because of the success of Captain Jack but I looked over lists and lists of people top 10, 20 or 100 pirate movies and you know what was on 50% of those lists – Pirates (2005), an adult film. And no one was putting it on their lists ironically. I think we can all agree that if porn can match the highest quality of a genre, the quality of most of the genre isn’t very high (to be fair, I have not seen this particular adult feature, so maybe it is the Citizen Kane of the adult film industry and I am being too hard on it, but I doubt it). Having said that, there were some gems I had forgotten and some classics I was excited to look at again. With out further ado here is the list, and we shall see on April 27th if the new pirate will stack up with what we have here (I know, I should have done some cliche pirate line, but I just couldn’t make myself).

25. Cutthroat Island (1995) Level IV – The Renny Harlin/Geena Davis collaboration 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. 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) Level V – 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. Pirates of the Caribbean: On Stranger Tides (2011) Level V – I remember listening to the Geekshow Podcast when this movie came out and one of the panelists made the perfect point about it. He said the thing about the pirates movies is that they are true family films in that you can bring everyone from 8 year olds to college kids, boys and girls, and they will all want to see it. That may not sound like a big deal, but those are hard movies to find.
22. Nate and Hayes (1983) Level V – He’s a scoundrel… A hero… A lover of danger and the last of the adventurers… This is the story of Bully Hayes! That’s the movie’s tagline. And if that doesn’t get you excited, how about this? It stars a young Tommy Lee Jones! He’s like a Texas pirate, how cool is that?
21. Treasure Planet (2002) Level VI – 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.
20. Pirates (1986) Level VI – 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 pretty 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.
19. Peter Pan (2003) Level IV – You may have missed this Peter Pan because it was buried by Lord of the Rings: The Return of the King and Cheaper by the Dozen (it may seem shocking to say Cheaper by the Dozen buried something, but it was a huge hit). This is the most beautifully filmed Pan and while it may not make you forget the Peter of your youth, if you were a youth when it came out this may well have become your Pan.
18. Treasure Island (1950) Level VI – 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. The Pirates of Penzance (1983) Level V – 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.
16. Yellowbeard (1983) Level VI – But, if you want to watch a pirate movie made in 1983 you should really 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. Swiss Family Robinson (1960) Level V – I really should have 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!).
14. Star Wars Episode IV: A New Hope (1977) Level VIII – Han Solo is a pirate AND the Millennium Falcon is a pirate ship. Obviously, Star Wars is not a purely pirate movie (which is why it isn’t higher on the 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!
13. The Island (1980) Level VI – 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.
12. Pirate of the Caribbean: At World’s End (2007) Level V – 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.
11. Peter Pan (1953) Level VI – 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 isn’t my favorite, but that doesn’t mean I still don’t look at it as a classic.
10. Waterworld (1995) Level VII – 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) Level VI – 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. Blackbeard’s Ghost (1968) Level VI – As I said, I loved Disney’s animated run that lasted 30 years, 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 and Dean Jones is as ever the perfect straight man. Hard to find now, but if you can it is definitely worth it.
7. The Sea Hawk (1940) Level VI – 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.
6. Serenity (2005) Level VII – To be honest, this is as much or more about Firefly the series (which, if it were a movie, would be a Level VIII or IX) as it is about Serenity, the movie Josh Whedon made as a continuation of the series. What 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. Look, if you haven’t seen the series watch it first (I think it is airing on the science channel on Sunday nights) 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.
5. The Goonies (1985) Level IX – 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.
4. Captain Blood (1935) Level VIII – 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) Level IX – 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. The Crimson Pirate (1952) Level VIII – 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. The 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.
1. Pirates of the Caribbean: The Curse of the Black Pearl (2003) Level VIII – 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.
I hope this got you excited for The Pirates: Band of Misfits (I put the trailer below if you haven’t seen it), or maybe a little excited to check out some of those lost pirate movies you haven’t seen in years and I apologize for not putting the adult pirates movie on my list. Maybe if I did a top 50.
Anyway, that’s my list, I could be wrong of course because, what do I know? I’m fat.

The 25 Greatest Pirate Movies Of All Time


and no, it isn’t all Johnny Depp and Errol Flynn.
If you have been reading this site for the last few months you have no doubt noticed that one of the movies I am most excited about in 2012 is opening this weekend — The Pirates – Band of Misfits. I think it looks hysterically funny and will be just the right movie for me and my 8 year old son to see and enjoy. With its release mere days away I figured what better time than to do a list of the greatest pirate movies of all time. That should be fun a relatively easy to come up with, right? Well, it turns out it was definitely fun, but not all that easy.
Hollywood has a long history with pirate movies to be sure, it just so happens that most of them stink. We forget because of the success of Captain Jack but I looked over lists and lists of people top 10, 20 or 100 pirate movies and you know what was on 50% of those lists – Pirates (2005), an adult film. And no one was putting it on their lists ironically. I think we can all agree that if porn can match the highest quality of a genre, the quality of most of the genre isn’t very high (to be fair, I have not seen this particular adult feature, so maybe it is the Citizen Kane of the adult film industry and I am being too hard on it, but I doubt it). Having said that, there were some gems I had forgotten and some classics I was excited to look at again. With out further ado here is the list, and we shall see on April 27th if the new pirate will stack up with what we have here (I know, I should have done some cliche pirate line, but I just couldn’t make myself).

25. Cutthroat Island (1995) Level IV – The Renny Harlin/Geena Davis collaboration 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. 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) Level V – 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. Pirates of the Caribbean: On Stranger Tides (2011) Level V – I remember listening to the Geekshow Podcast when this movie came out and one of the panelists made the perfect point about it. He said the thing about the pirates movies is that they are true family films in that you can bring everyone from 8 year olds to college kids, boys and girls, and they will all want to see it. That may not sound like a big deal, but those are hard movies to find.
22. Nate and Hayes (1983) Level V – He’s a scoundrel… A hero… A lover of danger and the last of the adventurers… This is the story of Bully Hayes! That’s the movie’s tagline. And if that doesn’t get you excited, how about this? It stars a young Tommy Lee Jones! He’s like a Texas pirate, how cool is that?
21. Treasure Planet (2002) Level VI – 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.
20. Pirates (1986) Level VI – 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 pretty 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.
19. Peter Pan (2003) Level IV – You may have missed this Peter Pan because it was buried by Lord of the Rings: The Return of the King and Cheaper by the Dozen (it may seem shocking to say Cheaper by the Dozen buried something, but it was a huge hit). This is the most beautifully filmed Pan and while it may not make you forget the Peter of your youth, if you were a youth when it came out this may well have become your Pan.
18. Treasure Island (1950) Level VI – 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. The Pirates of Penzance (1983) Level V – 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.
16. Yellowbeard (1983) Level VI – But, if you want to watch a pirate movie made in 1983 you should really 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. Swiss Family Robinson (1960) Level V – I really should have 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!).
14. Star Wars Episode IV: A New Hope (1977) Level VIII – Han Solo is a pirate AND the Millennium Falcon is a pirate ship. Obviously, Star Wars is not a purely pirate movie (which is why it isn’t higher on the 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!
13. The Island (1980) Level VI – 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.
12. Pirate of the Caribbean: At World’s End (2007) Level V – 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.
11. Peter Pan (1953) Level VI – 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 isn’t my favorite, but that doesn’t mean I still don’t look at it as a classic.
10. Waterworld (1995) Level VII – 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) Level VI – 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. Blackbeard’s Ghost (1968) Level VI – As I said, I loved Disney’s animated run that lasted 30 years, 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 and Dean Jones is as ever the perfect straight man. Hard to find now, but if you can it is definitely worth it.
7. The Sea Hawk (1940) Level VI – 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.
6. Serenity (2005) Level VII – To be honest, this is as much or more about Firefly the series (which, if it were a movie, would be a Level VIII or IX) as it is about Serenity, the movie Josh Whedon made as a continuation of the series. What 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. Look, if you haven’t seen the series watch it first (I think it is airing on the science channel on Sunday nights) 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.
5. The Goonies (1985) Level IX – 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.
4. Captain Blood (1935) Level VIII – 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) Level IX – 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. The Crimson Pirate (1952) Level VIII – 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. The 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.
1. Pirates of the Caribbean: The Curse of the Black Pearl (2003) Level VIII – 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.
I hope this got you excited for The Pirates: Band of Misfits (I put the trailer below if you haven’t seen it), or maybe a little excited to check out some of those lost pirate movies you haven’t seen in years and I apologize for not putting the adult pirates movie on my list. Maybe if I did a top 50.
Anyway, that’s my list, I could be wrong of course because, what do I know? I’m fat.