Captain Jack’s Top Ten Best Moments

With the fifth film in the Pirates of the Caribbean franchise premiering in just a few weeks, we’re reliving the first time we saw Captain Jack Sparrow drunkenly saunter along the pier in Port Royal. In celebration of Dead Men Tell No Tales, we are celebrating our favorite swashbuckler, Jack Sparrow–from his one liners, pathetic (aka: impressive) escape attempts, and the occasional BA moments that prove that he actually is the best pirate we’ve ever heard of–by ranking his top ten greatest moments in the franchise.

10. Jack’s less than stellar escape from cannibals
In Dead Man’s Chest, Will Turner and the gang find themselves searching the Caribbean to find Jack before Davy Jones, captain of the Flying Dutchman, finds him first. They find Jack on an island inhabited by cannibals who revere Jack as a god. All seems nice and cushy until Jack and the others realize that the cannibals are planning on having a BBQ and Jack is the main course. In typical Jack fashion, what begins as simply maniacally running for his life, ends in an unbelievable escape that survives being pummeled by fruit, spinning 360° in the air, falling through half a dozen wooden rope bridges, and almost becoming a pirate shish kebab.

Pirates of the Caribbean Trilogy Set

9. Politics
The way of the pirate life is slowly ending in At World’s End with Lord Cutler Beckett, chairman of the East India Trading Company, hanging anyone suspected of piracy. As a way to fight back, the pirate lords meet at Shipwreck Cove to decide the fate of the pirates and Calypso, a goddess that could be their only chance at beating Beckett. But, according to the Keeper of the Pirate Code, Captain Teague (aka: Jack’s father), only the Pirate King can decide the fate of Calypso. The pirate lords from all over the world fight and argue over who should be elected as their king and in the midst of the chaos, nominee for the coveted position of power, Elizabeth Swann, cries out, “This is madness!” and Jack’s simple, nonchalant response is, “This is politics.”

8. He might be compensating for something
One of the never ending jokes throughout the entire Pirates series is the competition between Captain Jack Sparrow and Captain Barbossa. Their rivalry began in The Curse of the Black Pearl and ran through Dead Man’s Chest, At World’s End, and even On Stranger Tides. Always debating who is the technical captain of the Black Pearl, the rivalry goes from shouting orders, navigating the ship, and of course, showing everyone who has the bigger spyglass…

Stream Pirates of the Caribbean: Curse of the Black Pearl Now

7. He may have deserved that
With a pirate’s life, there comes some staples: sand, rum, and a bit of… debauchery… Jack has had his fair share, enjoying himself whenever he arrives in Tortuga. Scarlet, Giselle, Ana-Maria, and even a mermaid just to name a few of the hearts he’s broken and the ladies who have slapped Captain Jack clear across the face. He deserves it… no matter what he may claim.

Pirates of the Caribbean tee shirts for me and women

6. Brilliance or madness? 
When Will Turner frees Captain Jack and asks for his help in getting his one true love back in The Curse of the Black Pearl, we see the first of Jack’s many brilliant, albeit ridiculous plans. Commandeering a rowboat, the unlikely duo uses it to successfully walk along the ocean floor to a nearby ship that they hope to use on their voyage. As Will Turner points out, “This is either brilliance or madness.” Funny how those two go hand in hand when we’re talking about Captain Jack.

Pirates of the Caribbean Four Movie Set

5. Epic spinning wheel sword fight
One thing that the Pirates franchise has is fabulous sword fight scenes. The most original of these can be found in Dead Man’s Chest between Jack, Will, and Norrington. While on Isla Cruces, the trio finds the chest of Davy Jones which holds his heart, but, unfortunately, each man wants  the heart for their own personal goals–Jack wants to call off the Kraken, Will wants to save his father who is trapped on the Dutchman, and Norrington wants to use it to gain a place back in the British Royal Navy–and so (of course) a sword fight breaks out. The epic three-way sword fight carries across the beach, into the jungle, and all over the island as our three heroes roll along a mill’s wheel. It’s both exciting and ridiculous at the same time… just like Captain Jack.

4. A grand entrance
Pirates have quite the reputation of being cold-hearted, murderous, power hungry villains always drunk on rum, but Jack’s first appearance is anything but intimidating and impressive. The soundtrack swoops into a crescendo and we see Jack staring intently at the horizon, the warm Caribbean breeze whipping through his dreaded hair… only to realize that he is sailing in a (literally) sinking ship. Always finding a way out of a sticky situation, Captain Jack sails on, clinging (nonchalantly) to the mast before lazily stepping off his ship and onto the pier of Port Royal. If that isn’t an entrance worthy of Jack Sparrow, I don’t know what is!

3. The East India Trading Company doesn’t stand a chance!
In At World’s End, after a series of parleys, deals, and lies, Jack finds himself on the Endeavor in the presence of probably the film’s biggest villain: Lord Beckett. As a way to save his own skin, he makes a deal with Beckett: spare him now and he will help him get to the pirate lords at Shipwreck Cove. As they shake hands, Barbossa and Sao Feng attack the Endeavor, offering Jack the chance to escape. Using a cannon to propel himself through the air, he safely lands on his feet “without a single drop of rum.”

Funko POP Vinyl Captain Jack Sparrow Action Figure

2. I’ve got a jar of dirt!
Captain Jack’s key to freedom is the heart of Davy Jones which he hides in a jar of dirt in Dead Man’s Chest (of course, no one tells him that the thump thump is actually not in the jar of dirt but with Norrington). When the Flying Dutchman appears before him and his crew, Jack parades around the deck singing, “I’ve got a jar of dirt! I’ve got a jar of dirt! And guess what’s inside it?!” This scene is hilarious and shows just how much of a wild card Sparrow can be… what makes it even better is that, according to fellow actors, it was completely improvised.

Pirates of the Caribbean Cursed Aztec Coin Skull Medallion at a Ridiculously Low Price

1.  Why is the rum always gone?
We all know that pirates and rum go hand in hand and no one should ever dare to take a captain’s rum away from him. But Elizabeth Swann does just that in The Curse of the Black Pearl and it has almost defined the film franchise ever since. Sparrow cries out, “Why is the rum gone?!” as Elizabeth uses it to build a bonfire on the tiny island they find themselves marooned on. And in subsequent films, Jack doesn’t forget it. Seeing Elizabeth for the first time in Dead Man’s Chest, he encourages Mr. Gibbs to hide the rum. I’ve been known to yell a few times, “Why is the rum gone?” and fans of the film consider that the quintessential moment of the franchise. Drink up me hearties, yo ho, indeed!  

And our official (unofficial) favorite Captain Jack moment happened only a few weeks ago, when Johnny Depp surprised Guests at Disneyland when he appeared as Captain Jack on the Pirates of the Caribbean attraction.

Captain Jack and his gang will be returning to the big screen in only a few weeks. Pirates of the Caribbean: Dead Men Tell No Tales hits theaters on May 26th.

Did your favorite Jack moment make it on our list? Or were you expecting Captain Jack Harkness? Let’s get chatting in the comments!

Amanda Woomer-Limpert is one of the Geekiverse’s newest writers and a former Disney Cast Member. She’s traveled through the Caribbean many times sipping on rum so she considers herself a pirate (obviously).  

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About Amanda Woomer-Limpert 39 Articles
A former Disney Cast Member slightly obsessed with cats, beards, Star Wars, and all things Disney!

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