Tear Jerker / Pirates of the Caribbean: Dead Man's Chest

• 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.
  "Hello, beastie."
• "Abandon ship. Into the longboat."
  • 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."
  • "Abandon ship. Abandon ship or abandon hope."
  • Also, the final looks of grief and horror from the crew as they watch the Kraken drag the Pearl under.
• "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.
• Davy 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.
  • The ending is worse when he he opens the chest only to see his heart is gone. He even lets out a sniff before he screams to the heavens.
  • His expression when Jack is telling him of Will and Elizabeth's situation. Perhaps he’s remembering when he was in love.
• 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 be doing. Bear in mind, this is the first time Bootstrap has seen Will since he was a child, so seeing him end up aboard the living hell known as the Flying Dutchman must compound the torture.
  • The dialogue after Will gets tossed into the hold once the flogging is done:
    Bootstrap: Will! [tries to help Will up, but Will shoves him away]
    Will: I DON'T NEED YOUR HELP!
    Bootstrap: The Bosun prides himself on cleaving flesh from bone. With every swing.
    Will: So I'm to understand what you did was an act of compassion?!
    Bootstrap: Yes.
• In the extended Liar's Dice scene, Will winds up winning the first round against Davy Jones to free his father from the Dutchman, but that ends up being a case of All for Nothing when Bootstrap willingly loses the second round. As Will mentioned, it was not about winning or losing the game. It was all about finding out where Davy Jones kept the key to the Dead Man's Chest.
• Seeing Norrington in Tortuga, a drunken broken shell of the man he used to be.
• In a sense, the Kraken's attack on the Edinburgh Trader. Sure, 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 crushed, torn apart and devoured by the Kraken for just being in the wrong place at the wrong time is just plain tragic.
• Bootstrap's reaction to the fact William helped Jack get the Pearl back, even though he doesn't know the context.

  "William? He ended up a pirate after all."