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- "There were dragons when I was a boy..."
- Every one of Stoick's reactions to Hiccup's Disney Death or kidnappings or simply getting into danger more than a modern child ought to:
- He gives a Big "NO!" 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 fake treasure, he and Stoick nearly get eaten by Alvin the Treacherous. When Hiccup 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, just as he is nearing home, a sea dragon breaks the ice and steals it. The others are cheering Hiccup for being The Chosen One 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 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 dies in his arms. This tragedy is a Cynicism Catalyst for Furious, who vows to wipe out all humans once freed from his chains in How to Break a Dragon's Heart, and a Heel Realization and Despair Event Horizon for Grimbeard. Becomes Fridge Horror 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 Trauma Conga Line after witnessing his family kill each other and then made the heir of boggy Berk by default.
- Camicazi 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 True Companions, but unlike Fishlegs she gives in to shock, tradition, and the witch's persuasive tones. Afterwards, she considers it My Greatest Failure, apologizes with Tears of Remorse to Hiccup when she comes across him in How to Seize A Dragon's Jewel and promises Undying Loyalty. Even more heartbreaking is that Hiccup lies that he never lost faith in her and she is Easily Forgiven. Talk about Character Development for an Ensemble Dark Horse!
- Hiccup's situation in How to Seize a Dragon's Jewel; 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 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 Calling the Old Man Out to his mother when she kidnaps him the second time and delivers him to Alvin and the witch. Even though it turns out 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 Snotlout betraying Hiccup, where all the Dragonmarkers curse out Snotlout and turn their backs on him and the witch delivers a "The Reason You Suck" Speech. Only Hiccup doesn't participate, knowing what it's like to go through that.
- Valhallarama becomes an Iron Woobie in How to Betray a Dragon's Hero, after the witch and Alvin have "proof" that 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 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.
- Snotlout's Redemption Equals Death 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 except Hiccup because there were just two boys, alone on a boat, going into the Wind of Woden. On the Island of Tomorrow, Gobber tells the Dragonmarkers about Snotlout betraying Hiccup to the witch. Snotlout's own father disowns him then and there.
- The fact that the aforementioned event plus surviving a shipwreck causes Hiccup to lose his memory. He's been through so much, but it takes an enormous Trauma Conga Line for his mind to erase his whole life. Even more heartbreaking is that he doesn't suffer Amnesiac Dissonance; 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 setting the Guardians of Tomorrow on him for not having the Lost Things and trespassing. Camicazi on seeing this releases a Big "NO!".
- Furious's Redemption Equals Death moment in turn. Namely he gets a Heel Realization when Hiccup tosses the real Dragon Jewel away, to show The Power of Trust and he ends up Taking the Bullet 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, "You are a hero. Rescue yourself." Even though it was useful advice and Hiccup did 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 he has to face Furious, with only Toothless for help.
- When Hiccup prepares to face Furious in what might be a Duel to the Death, Stoick confesses that he wishes he could go in his son's place, especially since 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.
- Furious' reaction to seeing 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 friendship between Hiccups and their dragons.
- Despite the above, Hiccup as an adult managed to mend his relationship with his mother. He mentions that she became a grandmother but retained her sense of adventure and questing.
- What Hiccup ultimately does 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 even his memories of the dragons and even Toothless are beginning to fade away into the myth. So not only is he dealing with dragons slowly vanishing before his eyes, he is also approaching the point where his life and age call into question the validity of what memories he retains.