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Tear Jerker: Pirates of the Caribbean
Curse of the Black Pearl
Barbossa's poignant death at the end of the first movie with his last words of "I feel...! ...Cold."
Not only that, but his absolute joy at being able to feel anything...then he remembers what it is and what it means.
the scene after Jack has made his bag of treasure and says to drop him off at the Black Pearl. Cut to Jack staring pathetically at the place the Pearl used to be. His beloved ship, the one that was stolen from him in a massive betrayal of his trust (which kinda screwed him up inside), the ship he spent ten years scheming to win back, has just been stolen from him again by people like Annamaria and Gibbs. And you feel deep sympathy for him, followed quickly by horror at the realization that without the Pearl, Jack — this guy we've dug from frame one and come to root for and love, who just masterminded the fight against Barbossa and fought an epic battle to save the day — can't escape and is about to be hanged. And he knows it. Then he says of his crew, his friends who've just betrayed him, "They've done what's right by them; can't expect more than that." That was so sad, even Will got upset.
Dead Man's Chest
The end of Dead Man's Chest - specifically, Jack's death, and the subsequent mourning in Tia Dalma's shack. The first was awesome to watch, but truly bittersweet, and the second was plain heartwrenching.
"Do not ask me to endure the sight of my daughter walking to the gallows, do not." Swann then gets a minor Heroic BSOD when he sees his plans to get Elizabeth to safety have been dashed.
Davey Jones's whole backstory is heartbreaking. He's ruthless and undeniably evil, but he's still mourning the loss of his true love. He still cries about it.
Davey Jones forcing Bootstrap Bill Turner to FLOG HIS OWN SON, lest the sadistic Bosun do it. Not wanting to see his son's flesh flayed from his back, he does it, and every lash puts the father in at least as much agony as the son. You can clearly see tears dropping his eyes in the middle of a rainstorm. (Bear in mind, this is the first time Bootstrap has seen Will since he was a child, and seeing him end up aboard the living hell known as the Flying Dutchman must compound the torture.)
At World's End
The Heroic Sacrifice of James Norrington. Also watch the beach scene near the end of At World's End.
He didn't fear death.
Not to mention it was Bootstrap, Will's father who killed him.
The death of Davy Jones. "Calypso..."
"Part of the ship, part of the crew..."
The beginning of the movie, at the gallows. Especially when that little boy looks up at the sky...
It was about there that most decided this is not a Disney movie, no matter what people tell you.
The scene with Elizabeth and Bootstrap on the Dutchman, where Bootstrap basically reveals he's resigned himself to misery forever, as saving him would mean giving up on his true love, and he doesn't think Will would or should make that decision. So he asks Elizabeth to convince Will to give up on him so he won't have to choose, and that it's too late: he's already part of the ship. Then, to drive the point home, we discover the ship has warped his mind so much that five seconds later he doesn't remember ever having the conversation. The whole scene is incredibly painful, in just how much Bootstrap has given up to despair.
"He won't pick me. (Bitter chuckle) I wouldn't pick me."
Lets not forget the death of Governor Swann even though we don't see him die. We just see him floating about in the afterlife. Made all the sadder by Elizabeth's reaction. "Take the line! Father, take the line!" "I'm so proud of you [...] I'll give your love to your mother, shall I?"
"Elizabeth. Are you dead?" "...no..." "I think I am." "No, no you can't be!"
Elizabeth screaming for her father to come aboard the ship and nearly jumping overboard to get to him. Not even Jack knows what to say. Hell, the entire crew - even Barbossa, Pintel and Ragetti - don't say anything. They just...blankly stare. It's times like that when you forget they're pirates.
Or indeed, the big death of the film: Will. Okay, so he pops back up again pretty soon after, but it's a pretty emotional scene, and on top of that, it also secures Davy Jones' chances of redemption as exactly nil. Of course.
The soundtrack can be quite tear-jerking as well.
Linked with a Crowning Moment of Heartwarming when Will's death motivates Jack to act to save him by giving up what he had been battling for the entire film. If it makes Jack stop thinking of himself, it must be serious.
Double points for how Will Turner ends up getting stabbed by Norrington's sword, i.e. the very sword he forged at the beginning of the first film. The movie really takes the "betrayal" theme to all sorts of interesting places.
the moment right before the parasail sequence, with Jack having to wrench Elizabeth from Will as the crew of the Dutchman gather to cut out his heart. Not only does this have one of the most heartbreaking declarations of love — "Don't leave me! I won't leave you!" — but the accompanying music turns into the chanting of an all boys' choir, which is almost always sure to elicit tears.
Elizabeth's "What shall we die for?" speech near the end of At World's End
watching Will and Elizabeth part ways on the beach and then after the stinger where Will returns to his love and his son who he hasn't even met yet
As evil and ruthless as he was, Beckett's death for some reason. His final, slow and deliberate march across the deck as his ship burns up behind him was incredibly poignant.
Even though he wasn't what you would consider one of the good guys, look at it from his perspective even for a second. It makes it ten times more emotional.
The handrail exploding behind his hand, for some odd reason.
Possibly because it missed him By That Much?
He was a bastard, but still...and then the panicked, muted cries of the people behind him as they dove overboard and he just completely lost it. Granted, it might have been scarier if he went insane, but this was a lot sadder. And then when you realized how much the others were flipping out and he was just quietly, slowly strolling along while the whole ship blew up...
Officer, disbelieving voice: Orders, sir?!
[sees Beckett not responding] Officer: ABANDON SHIP!
The quiet moment between Jack and Barbossa as they stand over the dead kraken and realize just how much their world is changing.
The death of the Kraken itself. It's frequently cited as a Missed Moment Of Awesome, but that was probably intentional. No heart-pounding, epic battle; no moment of brilliance or gallantry by the heroes. Instead, Beckett gives an order, and some of the magic and mystery of the world is quietly put to death. Jack's line on the subject, after Barbossa says the world's getting smaller, is icing on the cake:
Jack: "World's still the same, mate. There's just...less in it."
Every part related to the ending of the pirate's world. Which makes their victory at the end all the more Awesome.
On Stranger Tides
Groves' death near the end of On Stranger Tides
"Someone make note of that man's bravery."
Also from On Stranger Tides, the whole of Philip and Syrena's subplot,
On Stranger Tides again, in the end when Jack leaves Angelica on an island. Take into consideration that Gibbs had Jack admit that he has feelings for Angelica (and note, "feelings" is what Jack could barely manage to say, when "love" was the word he intended to say). Throughout the film ever since he met her again, Jack's been doing his darndest to keep Angelica safe. Then comes when he saves her life, and now he has no choice but to put as much distance between them because she'll be wanting to get revenge for his hand in her father's death. Being Good Sucks indeed for ol' Cap'n Jack.
One legged Barbossa resulted in a bit of Fridge Grief. Old Hector's getting older, which means so is everyone else. The End of an Age threatened in AWE seems to be creeping ever closer.
Barbossa's voice and expressions of horror while telling Jack about how The Black Pearl had turned against them was surprisingly painful to watch. And it might've been someone's imagination, but when he said "So I did what needed done." his voice had an edge to it like he was near shedding tears.
Jack's expressions as he's listening count, as well.
Then there's the end, particularly for Angelica. The entire escapade saw her torn between her father and the man she loved. She went to hell and back trying to save her father's soul, and in the moment it counted, Blackbeard put her up on the proverbial altar to be sacrificed. Still, her love for him and her desire to see him redeemed led her to comply. Then, thanks to Jack, she gets a second chance at life... at the expense of her father's. She watches him utterly consumed, stripped to the bones by the waters of the fountain. Then she is marooned by her love/"betrayer," with little hope of rescue. Even if she recognizes that Jack did it all to save her, HEARTBROKEN LIKELY DOESN'T BEGIN TO COVER IT.