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Avast me maties! It’s Talk Like a Pirate Day (TLAPD) once again on September 19th! Since 1995, this global holiday is about strapping on your buckler and hoisting the colors in the endless quest for a little booty. How can you participate? We’ve curated a fine share of movies to watch so you can be ready for your office meeting at four bells.
Treasure Island (1950)

Not only is this a fun Disney movie, it is also the origin of the pirate accent, so there is no better way to prepare for September 19th than to watch Treasure Island (book by Robert Louis Stevenson) on TLAPD eve! The movie stars Robert Newton, who chews up the scenery as Long John Silver, exaggerating his West Country (English) accent into pirate-speak. Is it historically accurate? Not in the least, but it is so much fun that it caught on, and we still imitate his accent to this day. The movie also does a nice job with real sailing lingo tossed in here and there, but overall, it’s just a fun movie if you’ve never seen it. The original book has spawned many retellings, including one from the muppets (with Michael Caine and Tim Curry) that is very fun.
- Amazon Prime Video (Video on Demand)
- Bobby Driscoll, Robert Newton, Basil Sydney (Actors)
- Byron Haskin (Director) - Lawrence Edward Watkin (Writer) - Perce Pearce (Producer)
Pirates of the Caribbean (2003-2017)

Yes, there are five Pirates of the Caribbean movies spanning 14 years. I’m pretty sure I’ve seen them all, but can’t remember which is which. The first one obviously introduces us to the main characters and we get different bad guys in each movie. Anchored by Captain Jack Sparrow (Johnny Depp) and rival Captain Barbarossa (Geoffrey Rush), we’ve seen everyone from Orlando Bloom, Keira Knightley, Jonathan Price, Chow Yun-fat, Penélope Cruz to a dozen others in this AAA Disney series. Don’t forget the absolutely rousing theme music and scores by the legendary Hans Zimmer! So break out your daily ration of rum and squeeze in a little citrus, ye scurvy dogs!
- Amazon Prime Video (Video on Demand)
- Johnny Depp, Geoffrey Rush, Orlando Bloom (Actors)
- Gore Verbinski (Director) - Ted Elliott (Writer) - Jerry Bruckheimer (Producer)
Master and Commander: Far Side of the World (2003)

I’ll take some liberty with including this one as a “pirate” movie, but hear me out. The plot takes place during the Napoleonic Wars and the HMS Surprise is hunting the Acheron, a French privateer, which is a ship that is authorized by a government during wartime to raid ships for commercial wealth and capture ships as prizes. It sure sounds like pirates hunting for booty to me. The film has the finest movie-length capital ship sea battle ever made. Crank your sound system to 11 and get ready to flinch as splinters explode from your screen. Starring Russell Crowe as Captain “Luck” Jack Aubrey and Paul Bettany as the ship’s surgeon (and naturalist) Stephen Maturin, the movie cost $150 million to make and used real replica sailing ships on the open ocean (the Surprise is in San Diego to this day). Based on Patrick O’Brian’s Aubrey-Maturin novels (19.5 of them), there’s plenty of sailing jargon to take in for TLAPD. So get ye to the foc’s’le and see if you can get Killick to make you some toasted cheese. (Just be careful shouting “Get to the foc’s’le!” because it is, indeed, pronounced fuk-sill.)
- Amazon Prime Video (Video on Demand)
- Russell Crowe, Paul Bettany, Billy Boyd (Actors)
- Alan B. Curtiss (Director) - Peter Weir (Writer) - Meyer Gottlieb (Producer)
Captain Blood (1935)

What respectable list of pirate movies wouldn’t include an Errol Flynn flick? Captain Blood is an early pirate film, but it is stacked with talent, from Basil Rathbone to Olivia de Havilland to a score by legendary Hollywood composer Erich Korngold. The plot is fairly complex, Flynn is witty, there’s a lot of swashbuckling swordplay, and even a really good romantic subplot. Who said pirates couldn’t be gentlemen around the wenches?
- Amazon Prime Video (Video on Demand)
- Errol Flynn, Olivia de Havilland, Basil Rathbone (Actors)
- Michael Curtiz (Director) - Casey Robinson (Writer) - Hal B. Wallis (Producer)
The Pirates! Band of Misfits (2012)

This is a kid-friendly stop-motion animated film that features Hugh Grant, David Tennant, Imelda Staunton, Martin Freeman, Jeremy Piven, and Salma Hayek. This misfit crew of wannabe pirates is largely unsuccessful in capturing any booty so they can win the Pirate of the Year award, but they do manage to capture the HMS Beagle, with Mister Charles Darwin himself on board. Shenanigans ensue. It is a very, very silly movie. Co-produced with Aardman Animations, the main characters are all traditional stop-motion puppets, but the backgrounds use a lot of CGI, which blends seamlessly together. And yes, this is the source of the rim-shot chimpanzee GIF meme.

- Amazon Prime Video (Video on Demand)
- Hugh Grant, Martin Freeman, Imelda Staunton (Actors)
- Peter Lord (Director) - Julie Lockhart (Producer)
Honorable Mentions
The TV series Black Sails (2014-2017) is a very adult show, but is based on historical characters (historical fiction) and is very entertaining, if a tad dark. The series wraps up nicely with a solid ending. Serenity and Firefly (2002-2005) are essentially pirate movies in space, right? They’ve got their own English/Chinese creole that pops out, but it isn’t exactly pirate-speak. Peter Pan (1953)? The Goonies (1985)? The Princess Bride (1987)?

