!!YMMV for the Book series
* AngstWhatAngst: Hiccup [[OnceAnEpisode once a book]] nearly gets murdered, eaten, drowned, and at worst gets nightmares later in life as an old man. He remains chipper about triumphing over ordinary Viking life, at least until [[WhamEpisode Book 9]].
** Then subverted in Book 12, where Hiccup from the trauma [[spoiler: loses his memory]].
* EnsembleDarkhorse:
** Camicazi, for being a BadassAdorable, taking on several grown swordsmen on her own, and acknowledging that Hiccup is "not bad for being a boy". Some fans wish she had been added to the movie.
** People also like Thuggory, the [[OnlySaneMan only sane Viking teen]] who isn't Fishlegs from another land -- the Meathead Island -- who admires Hiccup's ability to talk to a murderous Green Death and rallies the other boys to go with Hiccup's plan. Then he [[spoiler: takes the Slavemark]] to support Hiccup and his friends follow.
* EvilIsSexy: Alvin before he lost his hair got this treatment in-universe. He was quite a charming with the ladies apparently.
* FunnyAneurysmMoment:
* HarsherInHindsight:
** Any mention of Grimbeard The Ghastly, as well as his son Hiccup Horrendous Haddock II, Hiccup III's ancestor.
*** The Dragon Whisperer's way
*** Grimbeard's last letter, regretting how "treasure" tore his tribe apart, hence why he hid it. In ''How To Break a Dragon's Heart'' we learn [[spoiler: thanks to the witch]] that Grimbeard also [[spoiler: allowed a jealous son named Thugheart]] tear his tribe apart because of envy for Hiccup II.
* IronWoobie: Valhallarama of the White Arms in ''How to Betray A Dragon's Hero."
* JerkassWoobie:
** Grimbeard the Ghastly.
** Snotlout for some in book 11, when we see him lose everything [[spoiler: and realizing that even if he kills Hiccup, no one will follow him. Hiccup, despite injured and at swordpoint, convinces Snotlout to drop the sword and join him instead.]]
* TheScrappy: Snotlout eventually earns this status in-universe after [[spoiler: he betrays Hiccup one time too many]].
* ToyShip: Camicazi and Hiccup are usually shipped together, since they can be BackToBackBadasses and get along well.
* UnintentionallySympathetic:
** The Hairy Scary Librarian. Sure, he is AxCrazy and hoarding all the books in the library for himself and killing anyone who tries to steal said books, but he gives the thieves fair warning to return the books before he slices them up, and gets [[spoiler: sent to the Amber Slavelands because Hiccup frames him for stealing a Murderous Stealth Dragon]]. And when the witch lies to him [[spoiler:about receiving freedom]], he switches sides quite easily [[spoiler: after settling his score with Hiccup]].
** Furious as well. With the TraumaCongaLine that ensued after he lost his older brother [[spoiler: Hiccup II, Hiccup III's ancestor]], you can't blame him for believing that HumansAreBastards. While he doesn't hate [[NothingPersonal Hiccup III personally]], he doesn't want dragons to become slaves again or destroyed by the Dragon Jewel, and in his future vision he sees that Hiccup will become the MikeNelsonDestroyerOfWorlds for dragons.
* UnintentionallyUnsympathetic: Grimbeard the Ghastly, Hiccup's ancestor. It's hard to feel compassion for a guy that had no qualms about [[spoiler: enslaving the dragons and people alike after the Wodensfang tried to talk sense into him, abandoning his infant son for being a runt and stealing him from his MamaBear wife, allowing his wife to wander into the wilderness and presumably die of starvation, and then kill said son when the latter was trying to hold a peaceful protest for enslaved dragons. Then instead of fixing the mess he created, he banished the living son that he knew was a traitor, leaving an idiot heir on the throne, and rode off into the sunset after setting booby traps for his treasure and Lost Things]] He dug his own grave the minute that he wouldn't take the [[spoiler: Dragonmark.]]
* WhatDoYouMeanItsForKids: Except that it is, despite the amount of violence and trauma.
* WorldOfWoobie: Ho boy.
** You've got Hiccup himself, who has to undergo a huge TraumaCongaLine to become the Last Great viking Hero.
** His ancestor Hiccup II also has to count, given he has a ShootTheShaggyDog story and quite a traumatic childhood.
** His friend Fishlegs who is an asthmatic orphan and fellow runt; when he tries to find his ancestors on the island of Berserk, the Berserkers [[spoiler: laugh at him]].
** Stoick the Vast is also a bigger Woobie here than he is in the movies because he is DumbMuscle who [[PapaWolf loves his son]] and does the best that he can as a (mostly) single parent, chief, while not comprehending that the world needs to change and that change has a price. Not to mention that with his son nearly dying once a book he goes through a lot of AdultFear.

!! YMMV for the film version of ''How to Train Your Dragon'':
* AdaptationDisplacement: Due to the film's enormous popularity, the book isn't very well-known about in comparison.
* AngstWhatAngst:
** After the final battle, [[spoiler: Hiccup has but a few moments of remorse upon waking to find that he's lost his left foot and been given a metal replacement. But forget angst-- [[InstantAwesomeJustAddDragons there are dragons outside and they are now a part of the Viking village!]] There's also the fact that he lost his foot in battle like a ''real Viking'' -- which he had wished for all his life before befriending Toothless. Finally, he gets a big kiss from Astrid meaning he has the local ActionGirl as his girlfriend.]]
** Mixes with a bit of BookEnds as well [[spoiler: as Hiccup first helped Toothless deal with his missing tail fin, and now Toothless returns the favor by helping Hiccup learn to walk with his artificial foot]]. Considering that [[spoiler: he almost died, losing a foot probably isn't that big of a deal to him at the moment.]]
** The Tale of the Boneknapper which chronologically takes place after the events of the movie showcase Hiccup walking and running just fine on his [[spoiler: prosthetic leg]] which means that he has largely adapted to his injuries.
* AwardSnub: It came out the same year as ''WesternAnimation/ToyStory3'' and got overshadowed come award season. To the very least, it ''did'' come out on top for the Annie Awards (to the pleasure of its fans and disdain of Pixar fanboys).
** Losing the Academy Award for Best Original Score to ''Film/TheSocialNetwork''.
* CrossoverShip: Due to how both films were released in the same year, there's a fair amount of Hiccup[=/=][[Disney/{{Tangled}} Rapunzel]].
** And due to [[WesternAnimation/{{Brave}} another animated fantasy film set in roughly the same time period and setting]], Hiccup[=/=]Merida has been cropping up as well.
*** And even the Slash fangirls have their pairing, Hiccup and [[WesternAnimation/RiseOfTheGuardians Jack Frost]].
** Count the amount of fan arts that contain RMHJ in the same instance. That is the power preventing a Pixar/Dreamworks war.
* CrowningMusicOfAwesome:
** [[http://www.youtube.com/watch?v=KUWBm0Z-Xww Test Drive.]] Chills every time. If there was ever a piece written about the thrill of ''flying,'' it's Test Drive.
** Really, the whole soundtrack by John Powell can count here. It helps that key scenes were set to highlight the music in parts like "Forbidden Friendship," "Romantic Flight," and "Where's Hiccup" rather than with dialogue, often to great effect.
** And for further proof of its epicness, NBC Sports used "Test Drive" for its recap of Rory [=McIlroy=]'s historic 2011 U.S. Open run (setting the lowest score in the major's 100+-year history) during its coverage of the golf event.
** The [[AlternativeForeignThemeSong Japanese theme song]] isn't half bad either! Give it a [[https://www.youtube.com/watch?v=02hAAqAEwwY listen!]]
* {{Earworm}}: Jonsi' Sticks and Stones that plays at the end of the film is a song that won't be leaving your head anytime soon - it's addictive!
* EnsembleDarkHorse: Ruffnut. Just ask [[ImageBoards /co/]]!
* FantasticAesop: Don't judge dragons. They have hearts too!
* GrowingTheBeard: Widely considered the point where Dreamworks did this, and the moment when people started taking them more seriously than they had in previous years.
* HellIsThatNoise: When Stoick and the vikings first go to the island, their arrival is preceded by an odd, high-pitched twittering noise, which abruptly falls silent when they hit the shore. [[NothingIsScarier The effect is profoundly unsettling.]]
** In-Universe example: Vikings are shown to be ready and willing to fight any dragon alive, sometimes very enthusiastically. And yet, every single viking will load their pants the SECOND they hear the shriek of a Night Fury.
* InferredHolocaust: Although not seen, it's stated outright that the casualties for the Viking/Dragon war in general were large.
-->'''Stoick''': They've killed hundreds of us!\\
'''Hiccup''': And we've killed THOUSANDS of them!
** [[spoiler: While the Red Death didn't get the chance to wipe the Vikings out, we see many of them are very close to the ships as it sets them fire, which should have killed a number of them, but all we see are some falling into the water.]]
* MemeticMolester: Ruffnut will grope anyone and anything.
* PeripheryDemographic:
** Ratio of teenage fans to younger children?
* SelfFanservice: Thanks to her EnsembleDarkhorse position, Ruffnut gets a lot of this. In canon she's honestly not particularly pretty, largely because she looks a lot like her HalfIdenticalTwin brother Tuffnut (who isn't particularly androgynous either). But just wait until you see [[http://th00.deviantart.net/fs70/PRE/i/2013/307/8/2/ruffnut_by_kerrie_jenkins-d3ax2gm.jpg how the fans draw her...]]
* SomeAnvilsNeedToBeDropped:
** Violence isn't always the best solution, parents don't always know what's best for their kids, and just because something is a tradition does not mean that it is necessarily right.
** From the second movie, peace isn't always possible and some minds simply cannot be changed.
* TearJerker:
** [[spoiler: When Hiccup wakes up and discovers that he's lost his left leg in the battle; it's even more jarring if you didn't hear Gobber imply it earlier. Not to mention, the part Hiccup tries to walk using his artificial leg and immediately stumbles ''is like an emotional kick to the groin''.]]
** The scene where [[spoiler: Stoick disowns Hiccup. Hiccup pleads for him to listen for once in his life, is thrown back and told [[IHaveNoSon "You're not my son"]]. Hiccup's face as he watches his father leave really helped the tears flow, as does Stoick's expression after the door closes behind him.]]
** [[spoiler: Stoick mourning over his son's apparent demise in the aftermath of the fight with the Red Death. Granted, we all knew Toothless saved him somehow, but the sheer despair and sorrow in Stoick's voice as he grieves over the loss of his only son feels like a punch to the gut.]]
** Test Drive, strangely enough. There's just so much adrenaline and emotion that it gets kind of overwhelming.
* UglyCute: Dragons in general. [[NightmareFuel Except for the Red/Green Death, of course.]]
** The Terrible Terrors remind one of hyperactive, firebreathing chihuahuas. Enter the [[CrowningMomentofHeartwarming awwwww factor]] when one of them snuggles under Hiccup's arm and purrs itself to sleep there. A bit of trivia: That particular Terror was voiced by Paco the Chihuahua, after sound designer Nia Hansen of Skywalker Sound saw a video of him on Website/YouTube and paid his owners $100 for Paco's voice: [[http://www.youtube.com/watch?v=Mscd2rdiSUg video 1]], [[http://www.youtube.com/watch?v=M-ySyyo8wMg video 2]], [[http://www.cgsentinel.com/v2_news_articles.php?heading=0&story_id=4339&page=72 local news article]] [[http://cottagegrove.kval.com/content/hit-film-how-train-your-dragon-features-voice-chihuahua-cottage-grove article 2]].
** Toothless is this trope. [[http://i60.photobucket.com/albums/h36/myneed4speed911/Toothless/toothless.jpg there]] [[http://i60.photobucket.com/albums/h36/myneed4speed911/Toothless/toothless2.jpg are]] [[http://i60.photobucket.com/albums/h36/myneed4speed911/Toothless/toothless3.jpg a]] [[http://i60.photobucket.com/albums/h36/myneed4speed911/Toothless/toothless4.jpg few]] [[http://i60.photobucket.com/albums/h36/myneed4speed911/Toothless/1269926085276.jpg examples]] [[http://www.howtotrainyourdragon.com/downloads/1920x1200/Night_Fury_1920x1200.jpg on the]] [[http://images2.fanpop.com/image/photos/9600000/Hiccup-Toothless-how-to-train-your-dragon-9626254-1920-816.jpg web]]
** Gronckles, especially the one Hiccup tames with the dragon-nip and [[spoiler: the poor little guy that gets eaten]]
* ViewerGenderConfusion: Quite a number of viewers thought that Toothless was a girl when he first appeared. Unintentional feminine symbolism shows up around Toothless throughout the first film, such as Toothless looking at a bird's nest with eggs in it and holding onto an unconscious Hiccup like a dog or cat would cradle a newborn puppy or kitten.
** Also, the Red/Green Death. Due to Astrid's comparison of it to a beehive's queen, almost everyone refers to it as female. According to the books and Chris Sanders, the dragon is actually male, though there's really no indication one way or another in the movie.
* WinTheCrowd: Before this film, Dreamworks animated movies were typically thought of as a very distant third behind Pixar and Disney, overloaded with pop culture references and lowbrow gags. This is where it really started to be considered as a worthy contender next to those two.
* TheWoobie: ''Hiccup''. Before Toothless, he's friendless, motherless, viewed as huge disappointment by his dad, bullied by his peers, ostracized by the rest of Berk and a failure at everything Viking society values.
** Toothless for losing his tailfin and ability to fly, and possibly being the TheLastOfHisKind. (Or at least the only Night Fury among all the other dragons.)
* {{Woolseyism}}: Swedish dub: The word "hiccup" is directly translated to "Hicka" in Swedish, but since and "a" at the end would be the feminine form if used on a person (male names with an "a" at the end exists in Sweden, they're just ''very'' rare), they went for "Hicke", which would be the masculine form (pronounced "Hic-KAY").

!!YMMV for the DVD short film ''Legend of the Boneknapper Dragon'':
* NightmareFuel: The Boneknapper Dragon is a huge dragon that wears stolen bones like a giant flying skeleton, and will stop at nothing to find the perfect bone for its macabre coat of armor. Also, without a certain bone on its armor, it can sneak up on unwary Vikings since it can't roar.
* UglyCute: The Boneknapper dragon doesn't hesitate to warm up to Gobber and even allows him to give it a chin scratch when he gives it back the bone it needed to complete its armor and allow itself to roar.