Although pillaging, plundering, and going for months without showering are generally frowned upon in our society, it’s still fun to imagine what life as a pirate would be like. Who wouldn’t want to sail the seven seas with a band of misfits in search of buried treasure? Minus the questionable hygiene part, the idea of going full-on Jack Sparrow is pretty exciting.
Although real-life piracy is a no-no, pirates have been celebrated in fiction, television, and film for generations. From Long John Silver to James Hook, we’ve seen swashbuckling stories told and re-told in just about every way imaginable. It’s not all Pirates of the Caribbean, either. Starz’s Black Sails ran for four seasons to rave reviews. Peter Pan has been remade 5000 times, including as a stage play and musical. Pirates even have their own operettas!
Why “arr” we so obsessed with boat-dwelling, treasure-hunting thieves? We’re still trying to figure that one out. In the meantime, here are the best films that capture the essence of what it is to be a marauder of the seas.
Steven Spielberg handed 90s kids a film made of solid gold with Hook. In addition to making the film an in-depth character study of its title villain, Spielberg turned the classic tale of Peter Pan on its head by making Peter someone who did grow up—only to have to grow back down in order to rescue his captured children. Dustin Hoffman’s Hook is not a cartoon cutout here, but a man with feelings and ticks who, yes, is not above throwing his crew members into the Boo Box if they upset him. He’s so set on revenge that he travels all the way to grown-up Peter’s house (via flying ship?) to kidnap his kids. How’s that for epic piracy?
Treasure Island (1950)
Often considered the best pirate film of all time, Treasure Island was already a global phenomenon before its release thanks to Robert Louis Stevenson’s bestselling book. It was the first live-action film to be produced by Walt Disney Productions and remains the preferred adaptation to this day. The story follows Jim Hawkins, Captain Smollett, Squire Trelawney, and Long John Silver as they set out to find buried gold on none other than Treasure Island. Featuring an iconic performance from Robert Newton as Silver that has since set the bar for pirate voices everywhere, the 1950 adaptation also stars Bobby Driscoll as Hawkins, who just a few short years later would go on to voice Peter Pan.
Peter Pan (1953)
It’s not Peter Pan without pirates, especially the vengeful and menacing Captain Hook. Here he gets the full Disney treatment, making him more of a comic villain than in other adaptations but with his customary quest for revenge against Peter for chopping off his hand and feeding it to a crocodile. Hans Conried’s foppish Hook plays well against Bobby Driscoll’s free-spirited Pan, with the rest of the pirate crew rendered comically as well to make them more appropriate for younger audiences. This is one of the most famous versions of Peter Pan ever made thanks to Disney, shedding some of the original story’s darker themes and replaces them with colorful animation and memorable songs.
The Pirates of Penzance
Perhaps even more animated than Disney’s Peter Pan (despite being a live-action film) is Wilford Leach’s The Pirates of Penzance, adapted in 1983 from the Gilbert and Sullivan stage show. These pirates are singing, high-kicking goofballs whose choreographed swordplay is as tight as the tempos of their theatrical musical numbers. The story revolves around Frederic, a pirate apprentice who falls in love with the daughter of a Major-General only to learn that his duties as a pirate might conflict with his new romance. Penzance is beloved for its hilarious show tunes, mainly the famous “Modern Major General” number sung by the General himself. This film adaptation stars Kevin Kline as the Pirate King and Angela Lansbury as Frederic’s nurse, Ruth.
The Goonies might not feature a band of traditional pirates, but it does revolve around a group of friends on the hunt for the famous “One-Eyed” Willy’s hidden loot. They have to find it if they want to save their town from being bulldozed by a group of contractors looking to turn their neighborhood into a golf course. Directed by Richard Donner with a story from Steven Spielberg and a screenplay by Harry Potter’s Chris Columbus, The Goonies has become a fan-favorite for its thrilling action sequences and colorful cast of characters. It gave kids everywhere a reason to believe that adventure and excitement could be found right in their own hometowns if they were only brave enough to go looking for it.
The Princess Bride
A family story that merges pirates, giants, and princesses into one fantastical world, The Princess Bride is one of the most beloved films to come out of the 80s. Based on the book by William Goldman and featuring a screenplay by Goldman himself, the film centers around a farm girl named Buttercup who is in love with her dashing fellow farmhand Westley despite being betrothed to an evil prince. After Westley leaves to seek his fortune so he and Buttercup can wed, his ship is attacked by the Dread Pirate Roberts and he is presumed dead. Five years later, Buttercup is kidnapped by outlaws, and soon it’s up to the Dread Pirate Roberts (who might look a little familiar behind his black mask) to save her. The Princess Bride is an exciting ride from start to finish, filled with quotes as unforgettable as the characters who say them. The real treasures are the acting, the sword fights, and that most classic of lines, “I am Inigo Montoya. You killed my father. Prepare to die.”
It may not have all the bells and whistles of contemporary pirate films, but The Buccaneer tells an engaging fictionalized account of privateer Jean Lafitte’s assistance in the Battle of New Orleans. Yul Brenner stars as Lafitte, who must decide between helping Andrew Jackson and the Americans or side with the invading British. Here’s a rapscallion who at least tries to make a positive difference, even if it’s all to win the heart of the Governor of Louisiana’s daughter. The Buccaneer is the rare tale that features a pirate aiding the very men who are usually chasing him down, making it a treat for history and cinema buffs alike.
Swiss Family Robinson
This may not seem like a typical pirate film, but pirates play an important role in it and arrive at a pivotal moment in the plot. After the Robinson family is shipwrecked on a deserted tropical island, they must find a way to survive and make the strange new land their home. Not only do they find clever ways to live in the jungle, but they must ultimately defend themselves against the band of evil pirates that attacked their ship in the first place. Their brilliant Parent Trap-like defenses will make you howl with laughter and revel in their ingenuity. The rest of Swiss Family Robinson is equally enjoyable thanks to its dynamic cast and idyllic setting. In fact, the story is so beloved that Disney is revamping it into a new series for Disney Plus.
No pirate list is complete without Errol Flynn. He’s not only famous for his portrayal of Robin Hood, but also Captain Blood, “history’s most daring pirate,” philanderer, and reckless adventurer. Sweeping scores and sword fights galore await in this black-and-white adaptation of Rafael Sabatini’s 1922 novel. Captain Blood follows the title character’s journey as a young doctor who is falsely accused of treason, sold into slavery in Jamaica, and later becomes the most feared pirate in the Caribbean. Some aspects of the film haven’t aged well, like the over-the-top acting and Blood’s treatment of Arabella Bishop (played by Olivia de Havilland), but the film was among the earliest pirate stories to sensationalize the genre, leading to a sequel and inspiring countless other pirate films.
Muppet Treasure Island
Treasure Island but with Muppets? Yes please. All of your favorite Jim Henson characters can be found in this 1996 family comedy, with Kermit the Frog as Captain Abraham Smollett, Fozzie Bear as Squire Trelawney, and Miss Piggy as Benjamina Gunn. The real star of the film is Tim Curry as Long John Silver, who of course will stop at nothing to get to the island’s hidden treasure before the Muppets do. Muppet Treasure Island lends its own creative flair to Robert Louis Stevenson’s tale as well as its signature humor, musical numbers, and violence from Miss Piggy. It’s the perfect initiation into swashbuckling cinema for young children and an enjoyable treat for parents as well.
Modern-day pirates are alive and well in this edge-of-your-seat biographical drama. Documenting the real-life hijacking of the Maersk Alabama by Somali pirates, Captain Phillips is a high-octane ride that follows Tom Hanks’ Richard Phillips as he tries to stay alive, protect his crew, and get them all to safety before the pirates kill them. Given the contemporary nature of the hijacking and its heart-pounding plot, the pirates in this film are actually terrifying, led by newcomer Barkhad Abdi as Muse. His bone-chilling line “I am the captain now” became an instant classic, and the last five minutes of the film alone were enough to earn Hanks a Golden Globe nomination for Best Actor. Strap in—you’ll burn actual calories watching this one.
As if Disney hasn’t already produced enough renditions of Treasure Island, it offered another inventive take on the classic with 2002’s Treasure Planet. The story is essentially the same, but this time the pirate ships fly through outer space, John Silver is a cyborg, the treasure map is a glowing orb that casts three-dimensional laser coordinates into the air, and the crew’s destination is a planet instead of an island. Featuring the voice talents of Joseph Gordon-Levitt, David Hyde Pierce, Emma Thompson, and Brian Murray as Silver, Treasure Planet is a spectacular reimagining with clever updates that are perfect for young audiences experiencing this story for the first time.
Pirates of the Caribbean: The Curse of the Black Pearl
Easily the most prominent and thrilling pirate film of our time, Pirates of the Caribbean: The Curse of the Black Pearl introduced us to a new cast of characters inspired by Disney’s famed amusement park ride. More than just a recycled swashbuckling tale, the film bestows upon its evil pirates a curse that forces them to return every piece of Aztec gold they’ve stolen or else remain undead forever. Naturally, the plan isn’t easy to carry out with Jack Sparrow running around, brought to life by the incomparable Johnny Depp.
The film re-launched Depp as a chameleonic actor of comic genius and made instant stars of Keira Knightley and Orlando Bloom. While the rest of the films in the franchise weren’t as good as the original, The Curse of the Black Pearl remains the ultimate pirate adventure with plenty of twists and turns, a heart-pounding score, and an ending that makes you want to take the entire ride all over again.