Yo ho, all hands on deck! A brand new Pirates of the Caribbean adventure storms into theaters this month with Dead Man Tell No Tales, marking the return of everyone’s favorite thieves and scoundrels, including Will Turner, Elizabeth Swan, Captain Barbossa, and of course, the flamboyant swashbuckler himself, Captain Jack Sparrow. And while these buccaneers have raked in some serious booty over the years (the last adventure, On Stranger Tides, grossed more than $1 billion worldwide), they’ve also had their share of moments that have dumbfounded audiences everywhere.

Each new Pirates movie seems to be more convoluted than the last. While the tone of the first movie is rather tame, every sequel becomes bigger, wackier, and more confusing. The zany nonsense has intensified so much, that we thought we would look back at some of the kookiest moments that have happened to Captain Jack and the rest of the Pirates crew. These next 15 scenes that have raised eyebrows and dropped jaws, either for their overt violence, gross-out factor, or sheer ridiculousness. They’re the moments that have completely walked off the plank of disbelief, and have left viewers thinking “what did I just watch?!”

Here are the 15 Most WTF Moments in the Pirates of the Caribbean Movies.

15. Pirates in Drag (Curse of the Black Pearl)

Pirates of the Caribbean in drag Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

Kicking off our list is a rather strange moment from the first Pirates movie, Curse of the Black Pearl. While it has supernatural elements, the film is still (somewhat) grounded in reality. The main plot involves the dastardly Captain Barbosa as he leads his crew of ghostly pirates on a quest to win back their mortality, although the path getting there gets kind of weird.

After discovering that a British fleet is making their approach to their location, Barbosa and his ghoulish followers stage a surprise attack to catch the impending invasion off guard. Their strategy: sending two of their most incompetent pirates, Pintel and Ragetti, out on a dingy dressed in frilly dresses and bonnets.

There’s nothing more disturbing than a pair of rough-looking pirates in drag, especially undead pirates in drag. Somehow, Pintel and Ragetti are able to pass as ladies in peril, boarding one of the British ships and slaughtering most of the crew, a fate that’s at least better than laying eyes on these two beauties more than once.

14. Give Him a Hand (Curse of the Black Pearl)

Pirates of the Caribbean Skeleton Arm Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

We learn in the first movie that the crew of the Black Pearl is cursed by Aztec gold, becoming walking skeletons when under the moonlight. This might sound like a drag, but the Aztec curse does have its share of advantages, like becoming immortal. Unfortunately, the ghostly pirates lose that immortality just when they need it the most towards the end of the movie.

During the massacre on the British armada, Jack and Will are able to put in an end to the curse by tricking Barbosa in a sword fight. That’s bad news for the newly mortal pirates, who are quickly cut down by the opposing British army as their skeleton bodies turn back into flesh and blood. One of the more disturbing parts of the sequence is when Governor Swan places one of the pirates’ boney arms in a drawer. Realizing that the curse has been lifted, the frazzled Governor looks back into the drawer and sees the horrific sight of a severed human arm, flesh and all. Ew.

13. Jack’s Toe Necklace (Dead Man’s Chest)

Pirates of the Caribbean toe necklace Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

As long as we’re on the subject of severed limbs, this moment from Dead Man’s Chest is borderline sickening. Determined to run from his debt to Davy Jones, Jack Sparrow and the rest of his crew wind up on an island where Jack is deemed as chief by the local natives. Unfortunately for him, the natives are a bit on the cannibalistic side.

As if it wasn’t bad enough that they plan to cook and eat Jack, the tribe gives the eccentric pirate something that even he is creeped out by: a necklace threaded with cut off human toes. Confused and bewildered, Jack awkwardly takes the gift and puts it around his head as to avoid some unwanted confrontation.

Then, in typical Jack fashion, the pirate takes one of the toes and nervously bites off the toenail. Considering he’s about to be burned alive and eaten, it’s understandable that Jack isn’t really thinking as nibbles on some dead guy’s toe. Still, this is a pretty gross moment.

12. Human Bone Cages (Dead Man’s Chest)

Pirates of the Caribbean bone cage Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

While Jack is busy biting off human toenails, Will and the rest of the crew have a gross-out moment of their own. After landing on the island looking for Jack, Will wakes up in a bizarre looking cage hanging several hundred feet in the air; not the safest place you want to find yourself on an unfamiliar island.

Recognizing Gibbs and only a handful of the Black Pearl’s crew in with the cage with him, Will asks Gibbs where the rest of the Pearl’s crewmates are. In a dead-pan delivery, Gibbs responds by telling Will that the cages they’re in “weren’t built until they got here.” In a state of shock, Will realizes that he’s standing in a cage made from the human bones of the former crew. Gross as it may be, the survivors manage to come up with a plan to escape their disgusting prisons by flinging themselves towards a cliff and then scaling the side, which works out for half the crew, while the other cage plummets to their doom.

11. Fish Out of Water (Dead Man’s Chest)

Pirates of the Caribbean Davy Jones Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

Considering it’s a Disney franchise, Pirates of the Caribbean has had its fair share of disturbing deaths. Over the course of the four movies, characters have been shot out of canons, eaten alive, and cut up into tiny pieces. However, this swashbuckling sequence is definitely one of the more gruesome kills of the series, and possibly the grossest.

After Will finds himself in the presence of Davy Jones’ crew for the first time, he quickly draws his sword to engage them in combat. He soon finds this is easier said than done, as the crew of the Flying Dutchman is made up of half-human, half-fish monstrosities, including a pirate with the body of a hammerhead shark.

Not one to be intimidated, Turner quickly slices through his opponent’s stomach. To Will’s and the audience’s horror, several live fish spew out of the hammerhead’s newly opened stomach pouch. It’s a genuinely disgusting moment that might have felt right at home in a David Cronenberg flick, but not for a family-friendly Disney adventure.

10. Bootstrap Bill Whipping His Own Son (Dead Man’s Chest)

Pirates of the Caribbean Bootstrap Bill Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

We learn in Curse of the Black Pearl that Will Turner’s father, “Bootstrap” Bill, met his untimely demise by having has his bootstraps tied to a cannonball and fired into the murky ocean depths. This didn’t stop him from making an appearance in Dead Man’s Chest however as a member of Davy Jones’ ghastly crew. Unfortunately, his long-awaited reunion with his son wasn’t quite the heartwarming experience.

After discovering that the two are related, Davy Jones does the unthinkable and demands Bill whip his son in order to torment him. Though he’s at first reluctant, Bill ultimately gives in to Jones’ cruel demands. With tears in his eyes, Boostrap cracks the whip against his son’s back, creating one giant, painful laceration after another.

The twisted scene is a little hard to watch, even for the more seasoned moviegoer. We know it’s not as harsh as the whipping scene in 12 Years a Slave, but Bootstrap Bill’s tearful flogging of his own flesh and blood is still pretty brutal.

9. Jack Gets Eaten (Dead Man’s Chest)

Pirates of the Caribbean the kraken Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

Though Orlando Bloom and Keira Knightley found breakout success in the Pirates of the Caribbean franchise, it’s Johnny Depp’s Captain Jack Sparrow that absolutely stole the show. Flamboyant, charming, and instantly likable despite his morally bankrupt personality, Jack was everyone’s favorite pirate of the Seven Seas, until he was abruptly eaten by a kraken at the end of Dead Man’s Chest.

Throughout the second installment, Jack is on the run from Davy Jones’ personal sea monster, the kraken. After realizing that the vicious beast was never going to stop until it devoured its target, Elizabeth chains Jack to his ship to meet his doom. Viewers were stunned when the unthinkable happened and Jack plunged into the kraken’s spiky toothed mouth, sword first.

Of course, audiences knew it was just a matter of time before Jack made his triumphant return in At World’s End. Still, Sparrow’s gruesome fate was a bizarre way to end Dead Man’s Chest, which mostly just felt like a setup story for the eventual sequel.

8. A Child is Hanged (At World’s End)

Pirates of the Caribbean child being hanged Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

Every great movie needs a great opening, a hook to grab the audience’s attention right off the bat. Raiders of the Lost Ark starts with an adventurous introduction to Indiana Jones, Star Wars opens with a raid aboard a spaceship, and we get our first glimpse of the Joker in The Dark Knight’s thrilling bank heist. Each of these openings is memorable in its own way, but the intro scene of At World’s End is unforgettable for all the wrong reasons.

For some reason, someone thought it was a good idea to begin Disney’s third swashbuckling adventure with an extended sequence that shows various pirates and their families being hanged to death. It’s a depressing five-minute montage that shows one group after another meeting their untimely demise. It culminates with a small child who steps up to the platform below the noose. As if things couldn’t get bleaker, the boy begins to weakly sing a shanty until he’s put on top a barrel, noose placed around his neck, and dropped into the gallows below. Cue opening credits.

7. An Entire Crew of Jack Sparrows (At World’s End)

Pirates of the Caribbean Jack Sparrows Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

What’s better than one Jack Sparrow? Why, a hundred Jack Sparrows of course! At least, that’s what the team behind At World’s End thought. Though it might sound good in theory, in reality, an entire crew of Captain Jacks gets kind of annoying rather quickly.

After Jack’s untimely demise at the end of Dead Man’s Chest, he’s literally brought to the ends of the world, unable to die but not quite alive either. Stuck in a bizarre limbo with no one else to talk to, Captain Jack’s sanity kind of walks off the deep end. In some weird mechanism to entertain or keep his mind occupied, Jack’s psyche has split into multiple fragments, comprising a whole crew of Sparrows working aboard a ship beached on land. There are Jacks swinging from the rafters, Jacks scrubbing the deck, Jacks keeping an eye out for god knows what in the crow’s nest, and a Jack that even shoots another for something as trivial as a peanut. It turns out that even Jack can’t stand hanging around himself for too long.

6. Sao Feng’s Creepy Obsession (At World’s End)

Chow Yun fat in Pirates of the Caribbean Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

The third chapter of the original Pirates trilogy pulled out all the stops when it came to capping off the franchise, at least for the time being. There’s sea monsters, gods, supernatural specters, and a whole crop of brand new characters introduced within the franchise. One of these new comers was Sao Feng, played by Chow Yun-fat, the Hong Kong based Pirate Lord who kind of has a thing for the god Calypto. Like, an unhealthy, obsession kind of thing.

After crossing path with Elizabeth Swan, Feng convinces himself that this is his goddess in disguise, and goes to some pretty creepy lengths in order to live out his fantasy. He goes so far as to dress Elizabeth in traditional clothing, have her brought to him, and continue to make some uncomfortable, unwanted advances. When they’re fact-to-face, Feng calls Elizabeth by the name Calypso, and even mentions that he’s going to take her “fury.” We’ll leave it up to you to fill in the blanks of what this delusional pirate really means by that.

5. A Giant Pirate! (At World’s End)

Pirates of the Caribbean giant Calypso Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

Among other things, the Pirates movies have become known for becoming bigger and more unusual with each new entry. While the first movie was your classic ghost story, the sequels have gotten more outlandish, more fantastical. At World’s End is about as bombastic as it gets, with krakens, ghouls, ghosts, other dimensions, and one of the weirdest moments of the entire franchise: a 60ft tall pirate.

Common sense and the rules of logic fall off the plank in the third act of the movie, which results in a hodgepodge of different groups duking it out for the claim of the Seven Seas. Fighting on her own side is Tia Dalma, who is revealed to be the goddess Calypso (if only Sao Feng knew sooner). After finding out that Davy Jones had previously betrayed her, the goddess grows more than 60 feet high and starts bashing up pirates left and right. If that wasn’t enough to leave you stupefied, she then transforms into thousands of small crabs to engulf both the Black Pearl and the Flying Dutchman in a chaotic maelstrom. It doesn’t get weirder than this.

4. Death By Tentacles (At World’s End)

Pirates of the Caribbean bone Mercer dies Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

The Pirates of the Caribbean movies has never been short of violent and gruesome deaths. Throughout the series, characters have been hanged, stabbed, decapitated, burnt, and even eaten alive by sea monsters. But if we had to choose who got it the worst, it would definitely have to be Ian Mercer, who is horrifically killed by the many tentacles of Davy Jones.

Having the power over Davy Jones, Mercer becomes the commander of the Flying Dutchman during World’s End’s climactic battle. During the ship’s fight with the Black Pearl, a stray cannonball is fired into the helm of the Dutchmen, incapacitating Mercer’s troops. Jones takes advantage of the moment, and gives Mercer one of the most uncomfortable movie deaths we’ve ever seen. Jones plunges his slimy tentacles into every orifice in Mercer’s face, until the tyrant is left suffocated and lifeless. What a way to go.

3. Captain Keith Richards (At World’s End)

Pirates of the Caribbean Keith Richards Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

It’s no secret that Johnny Depp based the infamous Jack Sparrow on real life personas, notably Rolling Stones guitarist Keith Richards. The leisurely stroll, the dry wit, and even the obsession with booze (“Why is the rum gone?!”) are all trademarks of Richards that Depp managed to effortlessly capture with Captain Jack.

Perhaps this is why audiences were so stunned when the man behind the inspiration made a cameo appearance in At World’s End as none other than Jack’s father, Captain Teague. Equipped with his own crazy get-up, twisted beard, and acoustic guitar, Richard’s Teague is the stuff legends are made out of, earning him the fear and respect of all the other Pirate Lords of the Seven Seas.

Richards had such a blast playing the swashbuckling buccaneer that he decided to reprise the role for 2011’s On Stranger Tides. Though it hasn’t been confirmed yet if the Rolling Stones guitarist will pop up in Dead Men Tell No Tales, the fifth entry will feature another English rock icon: Paul McCartney from The Beatles!

2. Blackbeard Chooses Poorly (On Stranger Tides)

Pirates of the Caribbean Blackbeard Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

Remember the ending scene in Indian Jones and the Last Crusade when the villain drinks out of the wrong goblet? Remember how he grows long hair, becomes super old, and withers into dust? Well, now just imagine that same scene, but instead of just getting super old, the villain’s flesh is peeled off by a whirl pool until he’s nothing but bones.

That’s more or less the brutal death that awaited Blackbeard at the end of On Stranger Tides. After finally finding the fountain of youth, the villain takes a big gulp of the elixir at the expense of the life of his own daughter. However, Jack tricks Blackbeard into drinking from the wrong chalice. After he curses Jack, using his last breath, the pirate is engulfed in a rapid whirlpool that picks apart the villain’s skin until he’s nothing but a skeleton that collapses to the ground. It’s a heinous way to go, but honestly, Blackbeard’s fate was sealed the minute he decided it would be a good idea to trust Jack Sparrow. Much like the villain in Crusade, he chose poorly.

1. Killer Mermaids! (On Stranger Tides)

Pirates of the Caribbean mermaids Pirates Of The Caribbean: 15 Most Unbelievably WTF Moments In The Franchise (So Far)

Though the Pirates of the Caribbean movies started out as a simple ghost story (you best start believin’ – you’re in one), they quickly went head first into the fantasy realm, including giant sea monsters, ancient gods, and pirates made from squid-like tentacles. Among the various legends the series touch upon were that of mermaids, the underwater enchantresses of the deep sea. However, these aquatic beauties weren’t as friendly as you might think.

Introduced in On Stranger Tides, the mermaids in the Pirates universe are seductive sirens that aren’t exactly as bubbly as Ariel from The Little Mermaid. As a group of wary pirates paddle across the ocean, they’re visited by a mermaid that appears friendly at first, almost inviting. That is, until her seductive sea shanty lures her prey into the water. In a moment that catches the viewer off guard, the song stops, and the beautiful mermaid takes out her fangs, ready to chomp on her unsuspecting pirate victims. It’s a horrific moment that’s straight out of a Wes Craven picture, and sure to make you think twice the next time you see a half-human, half-fish person in the flesh.

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