Dustin Hoffman as Captain Hook holds Peter Pan (Robin Williams) hostage
(TriStar Pictures)

10 Swashbuckling Pirate Movies That Will Hook You at First Watch

There’s something so engrossing about pirate movies! Maybe it’s the costumes, or simply the concept of sailing the open seas, pillaging and whatnot. We’re not sure why pirate movies always hook us in, but we’re leaning in and picking our ten favorite pirate films of all time!

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Which one landed in our number one spot? Let’s find out, mateys!

10. Captain Phillips (2013)

Pirates point gun at Tom Hanks in Captain Phillips
(Sony Pictures Releasing)

We don’t usually think “true story” when we think of pirate movies, yet this biographical action-thriller is indeed based on real events. Captain Phillips is based on a memoir co-written by Captain Richard Phillips, an American merchant marine who was taken hostage by Somali pirates off the coast of Africa. The movie follows Captain Phillips (Hanks) at the helm of the Maersk Alabama cargo ship on April 8, 2009, as four pirates chase and eventually board the ship. Barkhad Abdi gives a standout performance as the head pirate, Abduwali Muse, who ultimately kidnaps the captain to use for ransom, resulting in a dramatic rescue by the U.S. Navy on April 12, 2009. Captain Phillips was a box office success, earning $220 million against a $55 million budget. The film also earned six Academy Awards nominations.

9. Treasure Island (1950)

Bobby Driscoll and Robert Newton in Treasure Island (1950)
(RKO Radio Pictures)

Robert Louis Stevenson’s 1883 novel Treasure Island has had more than its fair share of movie and television adaptations, but few are as delightful to watch as the original 1950 film directed by Byron Haskin. This movie is noteworthy for a few reasons; for starters, it’s the first fully live-action film Disney ever made. Secondly, it’s the first screen version of Treasure Island shot in full technicolor.

You know the story: a young boy named Bobby Driscoll (Jim Hawkins) meets an old pirate named Long John Silver (Robert Newton) and they set sail in search of buried treasure. This version has all of the swashbuckling action you want with a dash of that original Disney charm only old movies can claim.

8. Hook (1991)

Dustin Hoffman as Captain Hook holds Peter Pan (Robin Williams) hostage
(TriStar Pictures)

Steven Spielberg directed this movie inspired by J.M. Barrie’s classic Peter Pan story. The film follows Peter Banning (Robin Williams), an adult who has forgotten his younger years spent leading the Lost Boys as Peter Pan. Now a joyless, workaholic adult, Peter is forced to return to Neverland when his nemesis Captain Hook (Dustin Hoffman) kidnaps his children. Julia Roberts also stars as Tinker Bell, and Maggie Smith appears as Granny Wendy. The film was a bit of a flop at the box office, but it went on to become a cult classic with help from the internet.

7. Cutthroat Island (1995)

Geena Davis and Matthew Modine in Cutthroat Island
Metro-Goldwyn-Meyer

Depending on whom you ask, this is a rather controversial entry to the list! Cutthroat Island was so poorly received it set pirate movies back a decade in Hollywood. It’s listed in the Guinness World Records as the biggest box-office bomb ever, and it caused a production company called Carolco Pictures to close its doors for good. However, in recent years the movie has been slowly gaining popularity online, perhaps because it’s one of the only female-lead pirate movies in existence.

Geena Davis stars as Morgan Adams, a swashbuckling adventurer who inherits a treasure map and a pirate ship from her late father. Matthew Modine and Frank Langella co-star.

6. Muppet Treasure Island (1996)

The Muppet gang on the ship
(Buena Vista Pictures Distribution)

If you love The Muppet Christmas Carol (1992), and of course you do, then this Muppet version of Robert Louis Stevenson’s classic tale is a must-watch. This is the fifth movie that features the Muppets, and the second Muppets film produced by Walt Disney Pictures. All of your favorite furry Muppets are here in this classic re-telling, but some roles were played by live action actors. Tim Curry plays Long John Silver, newcomer Kevin Bishop plays Jim Hawkins, and the always Absolutely Fabulous Jennifer Saunders appears as Mrs. Sarah Bluveridge.

5. Captain Blood (1935)

Errol Flynn as Peter Blood and Olivia de Havilland as Arabella Bishop
(Warner Bros. Pictures, Inc.)

Errol Flynn was one of the original Hollywood swashbucklers, and Captain Blood is the film that put him on that map. Captain Blood is based on a novel of the same name by Rafael Sabatini. It’s about a doctor jailed on an island in the West Indies. He and the other prisoners escape the island and become pirates, and epic adventures follow. This was Olivia de Havilland’s fourth movie, and the role gained her and Flynn a great deal of clout in Tinsel Town.

4. Pirates of the Caribbean: Curse of the Black Pearl (2003)

Kiera Knightly and Orlando Bloom in "Pirates of the Caribbean"
(Walt Disney Studios Motion Pictures)

Hollywood executives wanted nothing to do with pirate pictures after Cutthroat Island tanked in the late 90s, but all of that changed when the first Pirates of the Caribbean movie crossed their desks. The script is based on the Pirates of the Caribbean ride at the Walt Disney theme parks. The story is about a pirate named Captain Jack Sparrow (Johnny Depp) and a lovesick blacksmith named Will Turner (Orlando Bloom). Turner is in love with Elizabeth Swann (Keira Knightley), who was kidnapped by the evil captain Hector Barbossa (Geoffrey Rush) aboard the Black Pearl. There’s also the little problem with a curse ….

3. The Pirates! Band of Misfits (2012)

animated pirates
(Sony Pictures Releasing)

Here’s a pirate movie that doesn’t take itself too seriously! If the stop-motion animation in this film looks familiar, it’s because production companies Columbia Pictures, Sony Pictures Animation, and Aardman Animations collaborated on this film a few years after producing Wallace and Gromit: The Curse of the Were-Rabbit (2005). The film is written by Gideon Defoe, who also wrote the book it’s based on, The Pirates! In an Adventure with Scientists. The action centers around a Pirate of the Year competition, and it features the voices of Hugh Grant, David Tennant, Imelda Staunton, Martin Freeman, Salma Hayek, and Jeremy Piven.

2. Peter Pan (1953)

Peter Pan faces off against Captain Hook
(RKO Radio Pictures)

J.M. Barrie first wrote Peter Pan, or the Boy Who Wouldn’t Grow Up as a play in 1904 and adapted it into a novel in 1911. It was later turned into a 1924 silent film before Walt Disney Productions produced this animated film version in 1953. The story is a familiar one: Wendy Darling (voiced by Kathryn Beaumont) and her two brothers meet Peter Pan (Bobby Driscoll) and travel to Never Land, where they stop growing older. Later, they square off against the evil Captain Hook (Hans Conried). The film was well-received, but modern viewers understandably have trouble looking beyond the terrible representation of Native Americans featured in the film.

1. The Princess Bride (1987)

Buttercup cowers behind Westley in The Princess Bride
(20th Century Fox)

You haven’t seen The Princess Bride? Inconceivable! This fantasy adventure was directed and co-produced by Rob Reiner (This Is Spinal Tap). It was adapted to film by the author of the book himself, William Goldman, who created the concept of a grandfather (Peter Falk) telling the story by reading his sick grandson (Fred Savage) a bedtime story. Like the book, the movie tells the tale of Princess Buttercup (Robin Wright ) and her love for farm boy Westley (Cary Elwes). When they’re separated, Buttercup is betrothed to the hateful Prince Humperdinck (Chris Sarandon), so Westley, who has assumed the identity of the Dread Pirate Roberts, must assemble a ragtag group of comrades to rescue her.

The movie was a moderate hit when it was released, but it gained cult status once it moved to home box office. Fair warning, however: There’s kissing in this movie!

Y’ar, mateys! Watching these films sure beats walking the plank, so what are ye’ waiting for?


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Author
Beverly Jenkins
Beverly Jenkins (she/her) is a contributing writer for The Mary Sue. She writes about pop culture, entertainment, and web memes, and has published a book or a funny day-to-day desk calendar about web humor every year for a decade. When not writing, she's listening to audiobooks or watching streaming movies under a pile of her very loved (spoiled) pets.