Top 10 Best Pirates of the Caribbean Franchise Moments

In the very first Pirates of the Caribbean adventure, Elizabeth Swann is kidnapped aboard the the Black Pearl, a ghostly ship sailed by Captain Barbossa and his crew of menacing, mangy pirates. Elizabeth reluctantly joins the Captain for dinner and quickly learns that these pirates are even more deadly in the moonlight. In fact, the pirates are walking skeletons, cursed by a lost treasure they plundered long ago. The crackling bones and ghastly skeletal visages make this scene the stuff of nightmares. Geoffrey Rush’s perfectly pirate-y performance adds a dash of devilish humor as he chugs a bottle of a wine and laughs with his crew. This wine drinking skeleton gag was actually inspired by a scene from the 1967 Disneyland ride that the movie was based on.

#9: Captain Jack Sparrow vs. Angelica “Pirates of the Caribbean: On Stranger Tides” (2011)

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The fourth Pirates adventure finds the infamous Captain Jack Sparrow in London, where he learns that he’s being impersonated by a certain someone. After a drink with his rockstar Dad at a rogue’s tavern, Jack finds the mysterious imposter. They tussle and topple over barrels of alcohol until the imposter is revealed to be Jack’s old flame, Angelica. This crossing of blades marks the return to the couple’s love/hate relationship. Although Jack has already faced ghost-pirates, cannibals, and sea monsters, Angelica knows all of Jack’s moves and proves to be a sly match for him. She also claims to be the daughter of the dreaded pirate, Blackbeard, causing Jack to keep a weathered eye on her motives.

#8: Will Turner & Elizabeth Swann’s Wedding “Pirates of the Caribbean: At World’s End” (2007)

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Getting married in the middle of a gigantic, thundering maelstrom might not sound very romantic. But, in a film where up is down and ships are sailed by mutated fish-pirates, this wedding ceremony actually turns out rather charming. When the battle against Davy Jones begins looking grim, Will and Elizabeth implore Captain Barbossa to marry them upon the chaotic deck of the Black Pearl. The pirate lovers perform some slippery multitasking, taking their vows while fighting off Davy Jones’s crew. Their original wedding in Port Royal was interrupted at the beginning of the second film, making this belated marriage all the more satisfying for audiences. Meanwhile, their battlefield kiss finally sealed the romance that had been brewing since the first film.

In this offbeat pirate adventure, Captain Jack is roaming the Caribbean in search of a mythical buried chest. But… leave it to Jack to unwittingly find himself sitting at the Chief’s throne before a tribe of crafty cannibals. While he fumbles around flinging coconuts as a human shish kebab, his crew takes a tumble down the mountain, trapped inside their mobile bone-cages. While these island hijinks are a bit cartoony, with Jack surviving a Wile E. Coyote fall into a deep chasm, they’re still a heck of a lot of fun!

If there’s one thing we know about Captain Jack, it’s that he almost always has a knack for escaping death by some manner of cleverness or improvisation. After saving Elizabeth Swann from drowning in Port Royal, Jack is met with little thanks from Commodore Norrington and Governor Swann. Sentenced to death for piracy, Jack conjures up an escape and makes it known that this would be a day long remembered. This was the first time we saw just how nimble and quick Jack could be. His daring, impromptu escape delighted audiences so that we’d be rooting for him through the whole film and more adventures to come. And we also begin to learn how fondly Jack feels about his hat.

#5: Fight for the Key “Pirates of the Caribbean: Dead Man’s Chest” (2006)

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Things get a little complicated when Jack and company arrive on Isla Cruces. Hoping to avoid death by Kraken, Jack is after the buried chest belonging to Davy Jones. The trouble is, everyone else wants it too. Will Turner arrives with the key and a three-way sword fight ensues between Will, Jack, and Norrington. This exhilarating sword fight features terrific stunt work and dizzying, fun imagery as the three key-coveters balance atop a rolling mill wheel. Clambering over the rolling wheel in a tropical jungle made this a difficult scene to film for the cast and crew, but the on-screen results were well worth it.

When these two larger than life pirate Captains have their showdown, they find themselves off the edge of the map in a moonlit cave inspired by scenery from the Disneyland ride. The ever so artful trickster that he is, Jack secretly palms a cursed coin, giving him leverage against an otherwise unbeatable foe. The treacherous Barbossa revels in swordplay and the vivacious musical score heightens the excitement. This highly imaginative sword fight has the two pirates bounding over heaps of treasure, leaping in and out of the moonlight, revealing their cursed skeletal figures. This supernatural twist, along with special effects ripe with creativity, makes this a truly memorable pirate sword fight.

#3: Will Turner Kills Davy Jones “Pirates of the Caribbean: At World’s End” (2007)

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Much of the suspense in At World’s End comes from the matter of who was going to kill Davy Jones. As Elizabeth’s father explains earlier in the film, whoever stabs the heart of Davy Jones, must take his place as Captain of the Flying Dutchman. This is a steep price to pay and not something to be taken lightly. During the battle with Davy Jones, Will’s life hangs by a thread and Jack gets his opportune moment to do the right thing. Will stabs the heart with a helping hand from Jack, proving that there’s more to Jack than just his wobbly walk and desire for immortality. Will and his father are saved, becoming part of the ship, part of the crew.

#2: Captain Jack Sparrow vs. Will Turner “Pirates of the Caribbean: The Curse of the Black Pearl” (2003)

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When young blacksmith Will Turner returns to his shop, he doesn’t expect to find an infamous pirate skulking about. It’s a good thing he’s been practicing his sword fighting skills because this is the day he crosses blades with Captain Jack Sparrow. Jack underestimates him at first, but Will knows a few tricks to hold his ground against the uninvited pirate. Will fights with a nobility and gusto that hearken back to the swashbuckling characters played by Errol Flynn. This scene is somewhat of a test for Will, as more perilous adventures on the high seas await him. Before we hoist our final pick, here are a few honorable mentions: Why Is the Rum Gone? “Pirates of the Caribbean: The Curse of the Black Pearl” (2003) Captain Jack Sparrow vs. Davy Jones “Pirates of the Caribbean: At World’s End” (2007) There Should Be a “Captain” in There Somewhere… “Pirates of the Caribbean: On Stranger Tides” (2011)

Arguably the coolest pirate in movie history, Captain Jack makes his grand entrance to Port Royal atop a sinking fishing boat. This was a perfectly humorous entrance for a very odd character, far different from pirate characters of the past. One of the reasons this scene works so well is that it tells us everything we need to know about this quirky pirate without the use of dialogue. Jack is a dashing, yet down on his luck pirate who’s about to make port in a town where pirates aren’t welcome. Just as his boat sinks to a halt at the dock, Jack takes his first step towards dazzling audiences with his quick wit, rebellious spirit, and adventurous charm.