The most memorable pirates in popular culture

Deciding to make a movie out of an amusement park ride? A bit of a risk. But it paid off big time for Disney. Pirates of the Caribbean: Curse of the Black Pearl was a huge hit and made Captain Jack Sparrow one of the all-time iconic pop culture pirates. Johnny Depp even got an Oscar nomination for the first movie. They’ve made several since, and Pirates of the Caribbean is now one of the highest-grossing movie franchises ever.

The 1922 novel Captain Blood by Rafael Sabatini spawned a few movies in the Golden Age of Hollywood. This adaptation from 1935 has quite the pedigree. In addition to being helmed by Casablanca director Michael Curtiz, it costars Errol Flynn, Olivia de Havilland, and Basil Rathbone. Three years later, they would star in The Adventures of Robin Hood together.

Treasure Island is a famous book you may have had to read in school. In terms of adaptations, we’d argue the most iconic of the bunch is the one from the Muppets. Hey, it has Tim Curry as famed literary pirate Long John Silver, after all.

The Pirates of Penzance is one of Gilbert and Sullivan’s most famous works — an opera that, if nothing else, gave Aaron Sorkin a variety of references to drop. Adaptations have been made literally dozens of times. There was also a movie done in 1983, which starred Kevin Kline as the Pirate King (and George Rose as the Major-General).

If you were a kid in 1985, you probably have a soft spot for The Goonies. Otherwise, you might find it overrated. Nevertheless, kids of the ‘80s have kept it in the national consciousness by talking endlessly about it. The movie is about the kids looking for the treasure of the One-Eyed Willy, and a lot of pirate stuff is key to the story.

In the fairytale riff that is The Princess Bride, everybody fears the Dread Pirate Roberts. When we meet him, it turns out that the current Dread Pirate is, in fact, our protagonist Westley. As you wish.

Throughout all the iterations of Peter Pan, you will find pirates. Specifically, one of pop culture’s pirate icons. We speak of Smee. Oh, also Captain Hook. In fact, the crocodile-fearing pirate is even the namesake of Steven Spielberg’s Hook, which is basically The Goonies for ‘90s kids.

Much of this pirate stuff we’ve covered so far has been on the lighter end. Black Sails is a little more serious but still an adventure show. It’s something of a prequel to Treasure Island, with Long John Silver being a character. They ended up mixing history in, though, as Edward Teach — a.k.a. Blackbeard — is a character in the third and fourth seasons.

The skull and crossbones flag is the iconic insignia of pirates. Naturally, there would eventually be a pirate show called Crossbones. This was a big swing from NBC, who gave us this show starring John Malkovich as Blackbeard. It didn’t prove successful enough, though, only lasting nine episodes.

Here is the one modern pirate story on the list and also the most realistic. Perhaps not coincidentally, it’s also the bleakest. Based on a true story, these pirates aren’t roguish swashbucklers. They are desperate men with automatic weapons. Tom Hanks gave quite the performance as the titular Captain Phillips. The film earned six Oscar nominations, including a Best Supporting Actor nod for Barkhad Abdi, who gave us the most remembered line: “I’m the captain now.”

Look, throughout the many iterations of Scooby-Doo, we’ve seen the gang face off with several ghost pirates. It feels like ghost pirates were the most-faced baddie. If Scoob and the crew were ever near the water, you could count on a ghost pirate. They even show up in one of the Lego Scooby-Doo movies. Yes, those exist.

Alfred Hitchcock made a pirate movie. It’s true. It’s based on a Daphne du Maurier novel, like Hitchcock’s Oscar-winning Rebecca. Notably, this was Hitchcock’s last British film before leaving to make movies in the United States.

How does every episode of SpongeBob begin? With the theme song. Who sings it? Painty the Pirate, an oil painting of a pirate. He even has an old-timey pirate voice. Let’s not forget Patchy the Pirate or the Flying Dutchman.

This is for the Englanders and Anglophiles in the audience. Captain Horatio Pugwash is a pirate character that began life in comic strips and books for kids. Since then, the captain has also received three TV series: one in the ‘50s, one in the ‘70s, and one in the ‘90s. That means three generations of kids growing up with Pugwash in their lives.

The Assassin’s Creed video game series sets its games all over the world and all over time. Black Flag takes place in the Caribbean during what was known as the “Golden Age of Piracy.” The main character in the game is Edward Kenway, a Welsh pirate who became a member of the Brotherhood of Assassins.

Cap’n Crunch has enemies. No, not just people who want to punish the roofs of their mouths. We’re talking about in-world villains. One is the pirate Jean LaFoote, who used to appear in ads for Cap’n Crunch. While we’re at it, let’s shout out former McDonaldland baddie Captain Crook.

Pirate movies had been huge in the ‘30s, ‘40s, and ‘50s. Then, they kind of disappeared. This is the rare old-school pirate movie between the ‘50s and Pirates of the Caribbean. Swashbuckler was not successful, but it had quite the cast. Robert Shaw stars, but there’s also James Earl Jones, Peter Boyle, and Anjelica Huston. 

In the ‘60s, Disney decided to make a pirate comedy. While many of those old live-action Disney films have largely been forgotten, Blackbeard’s Ghost was critically and commercially successful at the time. Disney regular Dean Jones was one of the stars, but so was Oscar-winner Peter Ustinov as the ghost of Blackbeard.

Henry Morgan was a Welsh pirate who became a privateer, basically a government-sanctioned pirate. The United Kingdom even knighted him at one point. This was after he went down to the Caribbean and raided Spanish settlements left and right. Morgan has popped up in pop culture here and there, but his name has made a massive splash in culture in one way. The rum brand Captain Morgan is named after him. He is arguably the name most synonymous with alcohol in the United States.