The 10 Best Pirates Who Sailed the Cinematic Seas

From left: Captain Hook (Jason Isaacs), Yeo-wol (Son Ye-jin), Captain Dola, Captain Blood (Errol Flynn), and Dread Pirate Roberts (Cary Elwes). (Image: Universal Pictures,Image: Lotte Entertainment,Image: Studio Ghibli,Image: Warner Bros. Pictures Inc.,Image: 20th Century Studios)
From left: Captain Hook (Jason Isaacs), Yeo-wol (Son Ye-jin), Captain Dola, Captain Blood (Errol Flynn), and Dread Pirate Roberts (Cary Elwes). (Image: Universal Pictures,Image: Lotte Entertainment,Image: Studio Ghibli,Image: Warner Bros. Pictures Inc.,Image: 20th Century Studios)

It’s time to grab a shoulder of rum and sit down to hear the tale of a group of pirates, who sailed the open seas (and air) in search of fame, adventure, and of course a buttload of cash. These are our top 10 pirates we’ve seen on film so far. Enjoy, or walk the plank!

Still remains one of cinema's most-baller moves. (Image: 20th Century Studios)

Dread Pirate Roberts (The Princess Bride)

I do wish. Cary Elwes stole our hearts and wallets as the Dread Pirates Roberts in The Princess Bride. Also know as Westley, he was the latest in a long line of Dread Pirates, carrying on the name with pride… and a gorgeous mustache. He was a serious badass, too. There aren’t many pirates who can train themselves to survive being poisoned, but that’s just one of the many things that made this Dread Pirate Roberts a master of the pirates arts.

I don't think any of us will ever feel the joy Tim Curry had every day on set. (Image: Disney)

Long John Silver (Muppet Treasure Island)

There are many incarnations of Treasure Island’s Long John Silver, but Tim Curry takes the cake for all the wild abandon he brought to the role in Muppet Treasure Island. He commanded every scene he was in — not only by literally commanding his ship of pirates but also by being someone you couldn’t look away from.

This is one pirate captain we'd be happy to serve under. (Image: Studio Ghibli)

Captain Dola (Castle in the Sky)

Castle in the Sky is a sweet Hayao Miyazaki anime about a young boy and girl who bond while searching for the lost flying city of Laputa… but it’s also a wild romp with air pirate Captain Dola and her many, many sons. Dola was first introduced as an enemy, an air pirate trying to steal Sheeta’s necklace, which held the key to Laputa. Eventually, Captain Dola became friends with Sheeta and her friend Pazu, helping them on their quest and looking great while doing it. Though I wish Captain Dola would’ve done more to curb her adult sons’ obsessions with the very underage girl.

Toss a coin to your pirate. (Image: Disney)

Captain Barbossa (Pirates of the Caribbean series)

It doesn’t matter how bad the Pirates of the Caribbean movies got by the end (and they got pretty bad), Geoffrey Rush was always a delight as Captain Barbossa. He fully embraced the Pirate’s Life, with a ridiculous accent and over-the-top facial expressions. Who can forget that scene in Curse of the Black Pearl where he chases Elizabeth Swan around the ship shouting “argh!” over and over? Through it all, he managed to give the villainous Captain Barbossa some humanity — which helps explain why they kept finding excuses to bring him back. To movies that didn’t deserve him.

Oh. It's you. (Image: Disney)

Captain Jack Sparrow (only in The Curse of the Black Pearl)

When we first met Captain Jack Sparrow (Johnny Depp) in The Pirates of the Caribbean: The Curse of the Black Pearl, he was a revelation. Funny, fascinating, and totally unpredictable. He always left you wanting more. Part of the reason Jack Sparrow worked so well was because he wasn’t the main hero of the story. He was a side character who didn’t need to have the spotlight always on him — he was going to steal it whenever he was onscreen regardless. Subsequent films turned Cap’n Jack into the main character, which was to his (and our) detriment. There’s only so much Captain Jack Sparrow you can take.

Yeo-wol (Son Ye-jin) knows how to swashbuckle and soothe whales with the best of them. (Image: Lotte Entertainment)

Yeo-wol (The Pirates)

The Pirates is a 2014 South Korean film about a female pirate captain named Yeo-wol (Son Ye-jin) on the hunt for the Ming Emperor’s Seal of State, which was lost at sea. She teams up with some mountain bandits to recover the seal, engaging in some impressive fight sequences that combine swashbuckling with martial arts. The movie can be pretty silly, with a lot of slapstick, but Yeo-wol stands out as a cunning and clever pirate captain with a compassionate side for whales — which definitely helps, since a whale had swallowed the seal they were all searching for.

Hello boys. (Image: Disney,Image: Universal Pictures,Image: ABC,Image: TriStar Pictures)

Captain Hook (Various Works)

Captain Hooks everywhere, take your pick! Even Jude Law is going to take on the title in the Disney live-action remake of Peter Pan. Captain Hook is one of those characters that actors love sinking their teeth into. He’s arrogant, flamboyant, and devilishly charming. But he’s got a dark side. He’s the kind of villain who can be pompous in one scene and viciously cruel the next. And yes, I did include Hook from Once Upon a Time in here, even though it was a TV show and not a film. Because you can’t feature Captain Hook without at least mentioning Colin O’Donoghue. You just can’t.

Sean Astin knows a legend when he sees one. (Image: Warner Bros.)

One-Eyed Willy (The Goonies)

It takes an impressive pirate to be a main supporting character after he’s already deceased. One-Eyed Willy might have spent the entire run of The Goonies being a dead person who’d inspired Mikey (Sean Astin) and his friends to search for his long-lost treasure, but he’s just as important a character as everyone else. Mikey spent much of the movie believing that he was being guided by the skeletal buccaneer, having conversations with One-Eyed Willy as the kids navigated his many traps and puzzles. He even had a full-blown confrontation with the guy at the end of his journey, one that showed the power One-Eyed Willy still wielded… long after his death.

The quintessential movie pirate. (Image: Warner Bros. Pictures Inc.)

Captain Blood (Captain Blood)

None of the pirates on this list can hold a candle (or rapier) to Captain Blood. Captain Blood was designed to ride the coattails of the “swashbuckler trend” that had surged in the 1930s with Treasure Island and The Count of Monte Cristo. It cast then-unknown actor Errol Flynn and the rest is history. Flynn became a household name thanks to his performance as the dashing and debonair pirate captain, who won love and battles in equal measure. If you want to know what movie set the stage for the handsome swashbuckling stars of The Princess Bride, The Pirates of the Caribbean, and just about every other pirate film in modern cinematic history, all you have to do is look at Captain Blood.

Just look at the joy on her face. That's the face of a happy pirate. (Image: Carolco Pictures)

Morgan Adams (Cutthroat Island)

Look, Cutthroat Island might not have been the best movie, but Geena Davis is still a badass pirate.