History TearJerker / PiratesOfTheCaribbeanDeadMansChest

* 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.

** His expression when Jack is telling him of Will and Elizabeth's situation.

* Bootsrap's reaction to the fact William helped Jack get the ''Pearl'' back, even though he doesn't know the context.

* Bootsrap's reaction to the fact William helped Jack get ''Pearl'', even though he doesn't know the context.

* In a sense, the Kraken's attack on the Edinburgh Trader. Sure, [[MauveShirt Captain Bellamy and his men]] weren't the most prominent characters, but they had enough time to be presented as sympathetic characters, and they'd gone out of their way to pick up Will after his escape from the Dutchman. Seeing them being [[CruelAndUnusualDeath crushed, torn apart and devoured]] by the Kraken for just being in the wrong place at the wrong time is just plain tragic.

* Seeing Norrington in Tortuga, a drunken broken shell of the man he used to be.

* Seeing Norrington in Tortuga, a drunken broken shell of the man he used to be.
!Meta
* [[https://www.youtube.com/watch?v=n_LApFnTfP8 Someone added lyrics]] to the Davy Jones theme. If you thought this musical piece couldn't be any more heartbreaking...
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* Davy Jones forcing Bootstrap Bill Turner to FLOG HIS OWN SON, lest the sadistic bosun, Jimmy Legs, do it. Not wanting to see his son's flesh flayed from his back, he reluctantly 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, communicating to viewers that this is ''the last'' thing poor Bootstrap wants to do. 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.

* [[https://www.youtube.com/watch?v=n_LApFnTfP8 Someone added lyrics]] to the Davy Jones theme. If you thought this song couldn't be any more heartbreaking...

* Davy Jones forcing Bootstrap Bill Turner to FLOG HIS OWN SON, lest the sadistic bosun, Jimmy Legs, do it. Not wanting to see his son's flesh flayed from his back, he reluctantly 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.)

* Davy 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.)

* Seeing Norrington in Tortuga, a drunken broken shell of the man he use to be.

* Seeing Norrington in Torgula, a drunken broken shell of the man he use to be.

* 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.)

** It's sad to hear Jack resign himself to abandoning the ''Pearl'', the thing he loves more than anything in the world, with the words "She's only a ship, mate."

* The end - 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.
** It's sad to hear Jack resign himself to abandoning the Pearl, the thing he loves more than anything in the world, with the words "She's only a ship, mate"

* 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.)

---> '''Bootstrap:''' Will! ''(tries to help Will up, but Will shoves him away)''

** It's sad to hear Jack consign himself to abandoning the Pearl, the thing he loves more than anything in the world, with the words "She's only a ship, mate"