[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/how_to_train_disneyscreencapscom_9993.jpg]]
[[caption-width-right:350:"I did this."]]
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[[folder:Book series]]
* "There were dragons when I was a boy..."
* Every one of Stoick's reactions to Hiccup's DisneyDeath or kidnappings or simply getting into danger more than a modern child ought to:
** He gives a BigNo when the Green Death eats his son in front of him, and is relieved when later on after Hiccup is sneezed out thanks to Toothless and sees that his unconscious child is breathing.
** In ''How to Be a Pirate,'' Hiccup first gets chased down by Skullions, and he only survives because Stoick protects him from the onslaught. Before, Stoick had been obsessed with getting Grimbeard's treasure, but Hiccup being in danger snaps him out of it. Then after that, just as Hiccup is moping that Snotlout found the [[spoiler: fake]] treasure, he and Stoick nearly get [[spoiler: eaten by Alvin the Treacherous]]. When Hiccup [[spoiler: seems to drown following the battle on the Lucky Thirteen]], Stoick tosses away the gold earrings he had gotten from the treasure chest.
* Hiccup's breakdown at the end of ''How to Cheat a Dragon's Curse'' might count. The boy has just spent the whole book getting run through the wringer as he tries to get an antidote (a potato) for his dying best friend. Then, [[HopeSpot just as he is nearing home]], [[YankTheDogsChain a sea dragon breaks the ice and steals it]]. The others are cheering Hiccup for being TheChosenOne who would get rid of the dragon. Hiccup has this reaction:
-->"I don't want to be chief of the Hairy Hooligan tribe! I didn't want to lift Norbert's stupid curse! I wanted to cheat the curse on ''Fishlegs''! All I want is my friend..."
-->He sobbed.
-->"All I want is my friend. Fishlegs trusted me. He thought I would make everything alright."
* The tears only work up harder when it turns out [[spoiler: Hiccup actually has the disease, and there is no potato in sight. Stoick is all but ready to charge out to sea and wrestle the potato from the Doomfang, and Old Wrinkly has to tell Stoick that it's IMPOSSIBLE to seek a cure, after saying that things are IMPROBABLE in the books. Stoick may not be the brightest Viking, but he loves his son.]]
* Hiccup Horrendous Haddock II's story, as revealed in ''How to Break a Dragon's Heart'': abandoned for being a runt, captured by his father Grimbeard the Ghastly when he and his dragon-brother Furious are discovered, forced to witness a world of human and dragon slaves that his father created. When he tries to have the dragons demonstrate peacefully for his freedom, his father kills him, thinking it's an act of rebellion. Grimbeard realizes too late that the real traitor was his other son Thugheart, and Hiccup II [[DiedInYourArmsTonight dies in his arms]]. This tragedy is a CynicismCatalyst for Furious, who vows to wipe out all humans once freed from his chains in How to Break a Dragon's Heart, and a HeelRealization and DespairEventHorizon for Grimbeard. [[spoiler: Becomes FridgeHorror when you learn that Grimbeard had the power to free all dragon slaves and become a better king with the Dragon Jewel, but he just chose to ride off into sea after dismantling his kingdom and exiling Thugheart; the whole book series could've been avoided if Grimbeard had taken responsibility for enslaving dragons and humans. In addition, you never hear how Grimbeard's surviving son Chucklehead handled the TraumaCongaLine after witnessing his family kill each other and then made the heir of boggy Berk by default.]]
* Camicazi [[spoiler: turning her back on Hiccup]] with the rest of the Vikings in ''How to Steal a Dragon's Sword''. She's supposed to be one of his TrueCompanions, but unlike Fishlegs she gives in to shock, tradition, and [[spoiler: the witch's persuasive tones]]. Afterwards, she considers it MyGreatestFailure, apologizes with TearsOfRemorse to [[spoiler: Hiccup]] when she comes across him in ''How to Seize A Dragon's Jewel'' and promises UndyingLoyalty. Even more heartbreaking is that [[spoiler: Hiccup lies that he never lost faith in her]] and she is EasilyForgiven. Talk about CharacterDevelopment for an EnsembleDarkhorse!
* Hiccup's situation in ''How to Seize a Dragon's Jewel''; [[spoiler: having spent so long isolated from human contact (or when there was human contact, they were trying to kill him) with only a small group of dragons for company, he's almost forgotten how to even speak Norse. Then [[FromBadToWorse his mother tries to kill him]], and the story starts. ]]
* The Windwalker looks positively devastated when he realizes he cannot come with Hiccup, Toothless and the Wodensfang into Fort Sinister because he's too big.
* Hiccup, Camicazi and the escape artists helping Eggingarde to escape in ''How to Seize a Dragon's Jewel'' and her subsequent reunion with Bear Mama. The readers aren't told anymore of what happens after the escape artists leave with her, but the little illustration of her smiling with her mother is enough to make any person smile/tear up a little.
* Hiccup CallingTheOldManOut to his mother when [[spoiler: she kidnaps him the second time and delivers him to Alvin and the witch.]] Even though it turns out [[spoiler: she does it to admit that he is the true King and rally supporters]], she doesn't speak at all to him even though a few words might have assuaged his fears. Hiccup ''does'' have a point in that she never answered his letters and has never been there for him, and Valhallarama ignoring him just proves his point.
* Seeing the aftermath of [[spoiler: Snotlout betraying Hiccup]], where all the Dragonmarkers curse out [[spoiler: Snotlout and turn their backs on him]] and the witch delivers a TheReasonYouSuckSpeech. Only Hiccup doesn't participate, knowing what it's like to go through that.
* Valhallarama becomes an IronWoobie in ''How to Betray a Dragon's Hero'', after the witch and Alvin have "proof" that [[spoiler: Hiccup has died]] and imply that Valhallarama's neglectful parenting was to blame. Valhallarama, unable to do any fighting on the Island on Tomorrow, then reveals that she has hoped to repair her relationship with Hiccup, since her fruitless quest kept her away from home for so long, once she got him crowned king. Makes one wonder how she felt when Hiccup yelled at her in the previous book for never being home and [[spoiler:for appearing to betray him]]. Slightly softened in that ''How to Twist a Dragon's Tale'' previously revealed that Valhallarama had a good relationship with Hiccup up to the day of her death, meaning they they reconciled at some point.
* [[spoiler: Snotlout's RedemptionEqualsDeath moment]] in ''How to Betray a Dragon's Hero'' was beautifully written, regardless of how you felt about the character.
** And no one knows about it [[spoiler: except Hiccup]] because there were just two boys, alone on a boat, going into the Wind of Woden. On the Island of Tomorrow, [[spoiler: Gobber tells the Dragonmarkers about Snotlout betraying Hiccup to the witch]]. [[spoiler: Snotlout's own father]] disowns him then and there.
* The fact that the aforementioned event plus [[spoiler:surviving a shipwreck causes Hiccup to lose his memory. He's been through so much, but it takes an enormous TraumaCongaLine for his mind to erase his whole life. Even more heartbreaking is that he doesn't suffer AmnesiacDissonance; with some summary from the Wodensfang Hiccup still acts like Hiccup and sails toward the island of Tomorrow to get crowned King before Alvin can.]]
* The Druid Guardian apologizing to Hiccup and commenting on his politeness before [[spoiler:setting the Guardians of Tomorrow on him for not having the Lost Things and trespassing.]] Camicazi on seeing this releases a BigNo.
* Furious's [[spoiler: RedemptionEqualsDeath moment]] in turn. Namely he gets a HeelRealization when [[spoiler: Hiccup tosses the real Dragon Jewel away, to show ThePowerOfTrust and he ends up TakingTheBullet for Hiccup when the witch tries to kill the boy. Although Furious could get the cure of the Vorpent Venom, since Hiccup found it in the fourth book, he decides to go into the sea and die alone, leaving Luna as the heir.]]
* Before the series started, Hiccup was kidnapped by the Murderous tribe. He wrote a letter to his mother asking for help, and languished in a dungeon for months His mother wrote back, "[[DareToBeBadass You are a hero.]] [[NoSympathy Rescue yourself.]]" Even though [[JerkassHAsAPoint it was useful advice]] and Hiccup ''did'' [[OffscreenMomentOfAwesome escape on his own]], without Toothless or Fishlegs or Camicazi, Valhallarama admits that she's terrible at being affectionate with her words. To make matters worse, she reiterates this advice to Hiccup before [[spoiler:he has to face Furious, with only Toothless for help.]]
* When Hiccup prepares to [[spoiler:face Furious in what might be a DuelToTheDeath]], Stoick confesses that he wishes he could go in his son's place, especially since [[spoiler: he thought Hiccup was dead at the end of the previous book]]. He then agrees to let his son go, despite his guilt. This is a stark contrast to Valhallarama's reaction.
* [[spoiler: Furious' reaction to seeing [[HeroicSacrifice Toothless jump in front of Hiccup]]. Furious failed because he jumped too late, but Toothless, a dragon like the size of an ant to Furious, still tried to protect Hiccup. This really goes to show the [[TrueCompanions friendship between Hiccups and their dragons.]]]]
* Despite the above, Hiccup as an adult managed to mend his relationship with his mother. He mentions that [[spoiler: she became a grandmother]] but retained her sense of adventure and questing.
* What Hiccup ultimately does [[spoiler:as king with the dragons and people don't change enough to promise peace with the winged beast: when he nears the end of his life, he has bards like Fishlegs spread rumors that the dragons are just imaginary creatures, and has Luna take the dragons into hiding. He ends up causing the end of an age of dragons, but by saving them from humans rather than wiping them out.]]
* Elderly Hiccup's epilogues at the end of every book are always poignant, but bittersweet and sad at the same time.
* By the end of the final book, Hiccup's monologues begin to mention that [[spoiler: even his memories of the dragons and even ''Toothless'' are beginning to fade away into the myth]]. So not only is he [[spoiler: dealing with dragons slowly vanishing before his eyes]], he is also [[spoiler: approaching the point where his life and age call into question the validity of what memories he retains.]]
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[[folder:Film Franchise]]
* ''TearJerker/{{How to Train Your Dragon|2010}}''
* ''TearJerker/GiftOfTheNightFury''
* ''TearJerker/DragonsRidersOfBerk''
* ''TearJerker/HowToTrainYourDragon2''
* ''TearJerker/HowToTrainYourDragonTheHiddenWorld''
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