Three Chic Geeks

For the nerdy and proud. Warning: spontaneous geekgasms may occur.

Arrr Favorite Pirates of All Time


large old paper or parchment background texture

Yarrrr! Happy Talk Like A Pirate Day, matey! We lasses here at 3 Chic Geeks  be celebratin’ this fine day by drinking grog and paying tribute to ye olde pirates. Whether they be fictional or historical, here lie our favorite pirates of yore.

1. Grace O’Malley

We’re not sure who started the “women are bad luck” on ships nonsense, but clearly they had never heard of Grace O’Malley (Irish: Gráinne Ní Mháille). Not only was she the leader of the the Ó Mháille clan in her own right, she was also the most famous female pirate to have ever lived. This here was a woman who led men and even allegedly verbally sparred with another great woman in her time – Queen Elizabeth I. She has rightfully become a staple in Irish folklore and is often referred to as the Pirate Queen.


2. Hook (Peter Pan/OUaT)

Whether you enjoy the original story, the animated Disney film, or one of the many incarnations since, Captain Hook is the most iconic fictional pirate of all time. And, in recent years, he’s been pretty darn sexy as well. We wouldn’t mind getting recruited for his ship.

3. Jack Sparrow

And what list would be complete without the pirate who made pirates cool again? Captain Jack Sparrow is the pirate we all aspire to be these days… well, sort of. We could do without all of the shenanigans and promising of our soul to Davy Jones. Today is the day to break out the Pirates of the Caribbean trilogy and relive all of Sparrow’s glory. What’s that you say? A fourth film? Oh, no no. You must be mistaken. There are only three, savvy?

4. Blackbeard

Edward Teach is quite possibly the most famous pirate to have actually existed. This has less to do with him being a particularly ruthless pirate as it did with him knowing how to create a fearsome image. In fact, it is said that Teach did not encourage the use of force, contrary to modern views of pirates. Teach was eventually killed in battle by Robert Maynard, though his legacy continues to live on to this day.

5. Ching Shih

Listen, this woman right here was a BAMF and there’s no two ways about it. Ching Shih was one of the most feared pirates of her time and well-respected by her crew… or, at least well-feared. You see, this woman governed her ship with a strict code. Rules included not dispensing one’s own orders (you would be killed), not stealing from the treasury (you would be flogged for a first offense, and thereafter killed), not cheating on one’s wife if you took one and not violating female prisoners (you would be killed! And if it was consensual, you would both be killed!). You have to admire a woman who raised her status in the world by being as ruthless as the men. She’s also one of the only pirates to have retired from piracy rather than being killed. You go Ching Shih!

6. Dread Pirate Roberts

The Princess Bride may not be a strictly pirate film, but it still features one of our favorite pirates of all time. Westley disappears and reappears as the Dread Pirate Roberts, a witty and talented rogue with a charming smile to boot. Plus, he returns to rescue his one true love from a terrible marriage. D’aww.

7. John “Calico Jack” Rackham

Calico Jack Rackham was a Cuban-English pirate who sailed in the Caribbean during the end of the golden age of piracy. Today, he is remembered for having had not one, but two female crew members. He also created the modern Jolly Roger, and that’s pretty dang cool. Rackham was captured in 1720 and hanged after only a short two-year stint as a pirate.

8. Anne Bonny and Mary Read

Anne Bonny and Mary Read are two of the most remembered female pirates and were members of Calico Jack’s crew. Anne Bonny came from a relatively wealthy family though she was disowned when she married a small-time pirate. She soon became disenchanted with her husband and began an affair with Calico Jack. Her husband attempted to have her punished and Jack offered to buy her freedom. However, Bonny refused to be bought and sold like a possession and ended up running off with Calico Jack.

It is said that Mary Read joined Jack’s crew while disguised as a man. Bonny became increasingly attracted to Read who was then forced to reveal her true identity. Jack grew jealous of Bonny and Read’s friendship until he too was informed of the truth. Read went on to become a valuable crew member.

When Jack and his crew were caught, the two women escaped hanging by claiming to be pregnant. Read died of a fever related to her pregnancy, while Anne Bonny seemingly vanished. It’s said that her freedom was likely arranged by her wealthy father.

9. Mal Reynolds

We had to include at least ONE space pirate on our list, and the spot went to none other than Captain Mal. While the crew of the Serenity may not seem like pirates, in truth most historical pirates were smugglers and privateers. Here’s to Captain Mal, one of the kindest (space) pirates to have ever existed.

10. Isabela (Dragon Age)

Once sold into a loveless marriage by her own mother, Isabela had her husband murdered, stole his ship, and became one of the most feared pirates in the Eastern Seas. Known for her rogue status, sharp wit, and her promiscuous nature, Isabela is a piratess who can easily run with the boys. And probably out-sail them.

Arrrr! Who be yer favorite pirate scallywag of all time? And are ye celebrating Talk Like a Pirate Day? Well don’t just sit there, you landlubbers! Tell us in the comments!


Author: Critique Geek

Writer and dreamer with a BA in Sarcasm. All-around nerd and lover of geeky things.

12 thoughts on “Arrr Favorite Pirates of All Time

  1. Oh, Captain Jack Sparrow is definitely my favorite. 😀

  2. How could you forget Steve the Pirate from Dodgeball?!? Added bonus, he’s played by Alan Tudyk who’s in Firefly with another favorite pirate. Yay!

  3. Can I just say that I LOVE the fact that Grace is number one?! Somehow she seems to slip through the cracks so easily despite being the fact that she’s a totally BADASS so the fact that she’s even on this list at all is amazing and also that she’s NUMBER ONE is incredible so just thank you

  4. Wot, no Long John Silver? The best of the best. ;As writ’: I don’t think he’s ever really been done justice on screen. (Come to think of it, I never want to see justice done to John.)

  5. My sweet Westley! Glad he made the list 🙂

  6. Jack Sparrow’s my favorite, savvy? My definition of sass is stepping off a sinking ship onto the dock.

  7. The Blackbeard museum in the Outer Banks, Ocracoke Island to be exact, is pretty cool. It’s small but it’s neat being there at Teach’s Hollow.

  8. Ah, I have a special place in my heart for The Pirate Captain in the Pirates! books and the film Pirates! band of Misfits. He’s just delightful. Also Hugh Grant.

  9. Oh, gosh…how can I choose a favorite??? (This is the Fandom Wars all over again!)

  10. Grace O’Malley of course!

  11. The Dread Pirate Roberts was actually a real pirate, as well. The character in Princess Bride was named after the Dread Pirate Robert Searles who sacked Saint Augustine.

  12. Much as I like Mal, I’m not sure it’s fair to include space pirates without counting Han Solo.
    But regardless, Grace O’Malley wins.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s