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10 Fictional Pirates Who’ve Stolen Our Hearts

For centuries, pirates have held a romantic allure for the masses. Who doesn’t love the idea of seafaring outlaws who follow their own destiny, seeking treasure and glory? In real life, of course, piracy is not so much romantic as it is terrifying. But that doesn’t stop us from craving exciting tales of swashbuckling adventurers in swoopy blouses (think Adam Ant in the “Goody Two-Shoes Video”) and gold earrings.

Here are ten of our favorite fictional pirates:

  1. Dread Pirate Roberts, The Princess Bride

The Princess Bride Dread Pirate Roberts Cary Elwes

The Dread Pirate Roberts (Cary Elwes), also known as Westley the Farm Boy and The Man In Black, is the epitome of sophistication in his classic black outfit, a look that is both fierce and slimming – we approve. He climbs the Cliffs of Insanity, duels left-handed, and outwits clever villains who attempt to poison him with iocaine powder. He also scares the bejeezus out of Prince Humperdink by threatening to duel him to the pain. No wonder Princess Buttercup is in love.

  1. Captain Jack Sparrow, Pirates of the Caribbean

Pirates of the Caribbean Jack Sparrow Johnny Depp

Captain Jack Sparrow (Johnny Depp) is proof that you can rock a flawless smoky eye and be the legend of the seas at the same time. He is both charming and morally bankrupt, which makes him so much fun to watch. He’s perpetually tipsy, totally avaricious, and continually in search of rum and personal gain – the kind of trickster who will steal your ship and your heart.

  1. Tia Dalma, Pirates of the Caribbean: Dead Man’s Chest

Pirates of the Caribbean Tia Dalma Naomi Harris

Tia Dalma (Naomi Harris) isn’t just a badass lady pirate with amazing dreds. She is literally a goddess imprisoned in the body of a mortal woman. Before she was Tia Dalma, she was Calypso, daughter of Atlas, goddess of the sea. But even goddesses have their weaknesses, and hers was the young Davy Jones, who turned out to be a terrible boyfriend because he plotted with the Brethren to imprison her in a human body. Eventually, Calypso-in-human-form became Tia Dalma, a voodoo-practicing pirate who bided her time until she could seek revenge. We’re here for it.

  1. Captain Killian Hook, Once Upon a Time

Once Upon a Time Killian Hook Colin O'Donoghue

Before arriving in Storybrooke, Killian Hook (Colin O’Donoghue) was an officer in the Royal Navy. He turned to piracy after finding out his king was corrupt. He has a sweet ride named The Jolly Roger, and falls in love with difficult women. First, Milah, the wife of Rumplestiltskin, which turns into a whole thing, and later, Emma Swan, who takes “playing hard to get” to a whole new level. Nonetheless, we are proud sailors on the ship CaptainSwan. He’s a rogue with a heart of gold who would do anything to protect the ones he loves.

  1. Captain Hook, Peter Pan

Peter Pan Captain Hook Jason Isaacs

This iteration of Captain Hook (Jason Isaacs) is darker than you’d expect in a film based on a children’s story. He’s menacing and enticing at the same time, in a way that makes viewers a little uncomfortable, given that Wendy, who Hook wants as one of his own pirates, is still a child. Fans of the original story will recognize Captain Hook as the grownup whose inner child, a.k.a. Peter Pan, has disappeared, leaving him old and bitter. Here, Captain Hook is both tragic and compelling.

  1. Captain Flint, Black Sails

Black Sails Captain Flint Toby Stephens

In this series, which is a prequel to Robert Louis Stevenson’s Treasure Island, Captain Flint (Toby Stephens) is a disgraced naval officer turned pirate. He’s a fascinating character, as we learn that he was once deeply in love with Lord Thomas Hamilton while serving in the Royal Navy, and the discovery of their relationship is what set in motion the events leading to his piracy.

  1. Anne Bonny, Black Sails

Black Sails Anne Bonny Clara Paget

Anne Bonny (Clara Paget) is based on a real female pirate from Ireland who became one of the most well-known pirates of her time. In Black Sails, her character comes from an abusive marriage which she escapes when one day, in a tavern, a man sees her being hurt and slits her husband’s throat. She runs off with him and never looks back. She’s beautiful, tough, violent, and above all, a survivor.

  1. Han Solo, Star Wars

Star Wars Han Solo Harrison Ford

What’s sexier than a pirate? A space pirate. Han Solo (Harrison Ford) is a dashing scoundrel, smuggler, and later, a leader in the Rebel Alliance. He won the Millennium Falcon in a card game with Lando Calrissian, and it’s souped up system makes it a huge asset not just in transporting stolen goods but in fighting the evil Empire. Also, he looks good in vests, has a rakishly irreverent sense of humor, and we love him (he knows).

  1. Stephen Bonnet, Outlander

Outlander Stephen Bonnet Ed Speelers

Stephen Bonnet (Ed Speelers) is an Irish pirate first encountered by Claire and Jamie Fraser in the Charleston, South Carolina. He first appears in the Outlander books in Drums of Autumn, where Jamie, against his better judgment, helps him to escape the guards who want to return him to prison where he will be hanged. He seems to be without morals or compassion, but when Jamie and Claire’s daughter, Brianna, finds herself pregnant after some…transactional sex (we’d call that assault), he gives her a black diamond to take care of the child who might be his. He’s not really a character we can love, but he is complex and fascinating. He’ll appear in season 4 of Outlander this fall.

  1. Pablo, The Backyardigans

Backyardigans Pablo Pirate

Okay, so Pablo the blue penguin from The Backyardigans actually only played a pirate in one episode (“Super Team Awesome”) but still. He is a blue penguin who sings. And dresses up as a pirate. We love him. He’s amazing and we will fight anyone who says different.

Oh, and here’s that Adam Ant video!

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