!!Book series
* In ''How to Seize a Dragon's Jewel'', Alvin the Treacherous catches Hiccup and orders a huge group of slaves to bring him forward ... So Hiccup essentially crowd-surfs them towards his doom, all the while having a sweet conversation with Stoick and completely ignoring Alvin's mother screeching at them to shut up.

!!First film
* Toothless's celebration right after the Test Flight scene where he and Hiccup learn to fly together. Toothless blows out a fireball for himself to fly through, then sails towards it with this expression of pure, sublime bliss - and drags Hiccup along for the ride.
-->'''Hiccup:''' "Oh, come ''on''".
* Toothless's expression after Hiccup puts the fin on his tail for the first time. "Duuuuuude."
** Not to mention his face when he first realizes something is going on back there. The range of expressions he goes through is priceless to watch.
*** Plus while the camera is focused on Hiccup putting the fin on, you can see in the background Toothless starting to spread his wings so you just *know* what's going to happen.
* Hiccup using his intimate knowledge of dragons to seemingly "subdue" them while not actually hurting them.
* Toothless depositing a half-eaten fish on Hiccup's lap - and the look on Toothless' face, as if to say, "Go ahead, eat it!". Hiccup's trying it, and forcing himself ''not'' to vomit. Then Toothless gestured for him to swallow it, to which Hiccup does the silent version of "you're serious?". And after Hiccup swallows it, Toothless licks his lips as if to ask, "Did you like it?"
** Prior to that, when Toothless discovers the knife Hiccup has with him, Hiccup drops it and Toothless gestures to the lake with his head as if to say, "Get rid of it." Once Hiccup does so, Toothless immediately goes into cute mode.
* The "Thank you for nothing, you useless reptile." line, delivered totally [[DeadpanSnarker deadpan]] while Toothless is going through his most extreme aerobatics to try and terrify Astrid into saying sorry.
* Hiccup's (well justified) fainting dead away after Toothless counts coup [[MightyRoar with a thunderous roar]] in his face, then tries to flies away. Hiccup stays awake just long enough to see Toothless go down, turns around, then drops like a stone.
* Toothless vs the Terrible Terror. [[PokeThePoodle Toothless wins.]] Cutest territorial match ever.
** For the curious, the Terror [[spoiler:puffs up, preparing to breathe fire... and Toothless beats him to the punch by blowing a little bit into his mouth.]] And thus we have [[{{Foreshadowing}} "Not so fireproof on the inside, are you, little guy?"]]
* The look on Toothless' face as he and Hiccup prepare to take back Astrid to the ground. If he were human, he'd bust out a PsychoticSmirk.
-->[[TemptingFate "See? Nothing to be afraid of."]]
* Hiccup showing Toothless the saddle for the first time and having to chase him around to get it on.
** It's even funnier if you slow down the video a little, you can easily see Toothless smiling with his puples wide. He isn't running around because he perticularly objects to the staddle, he just thinks it'd be fun to make Hiccup chase him around some.
* Astrid's introduction. It's practically going "LOVE INTEREST HERE" with SloMo flames and Hiccup's goo-goo eyes.
* When Gobber is telling the recruits about how his leg and arm got eaten by dragons we get this gem from Snotlout
-->'''Snotlout:''' I swear I'm so ''angry'' right now! I'll avenge your ''beautiful'' hand, and your ''beautiful'' foot! I'll chop off the legs of every dragon I fight. With my '''FACE!'''
* The bit when Toothless is trying to ignore Hiccup just after the fish eating scene. He notices Hiccup sitting near him and, clearly exasperated, shuffles his tail round to hide his face. Then, as Hiccup reaches out to touch, peeks from under the tail, leaving Hiccup to stroll away nonchalantly.
* "You're right, you're right. You're right! I'm through with the lies. I've been making...''outfits''."
** A few seconds later, as Astrid is trying to see what's making the noise she keeps hearing, Hiccup tries to stop her by surrendering himself. Astrid responds by taking his hand off her shoulder ''and snapping it''. Hiccup's indignant response caps it off:
-->'''Hiccup:''': Oww! Why would you ''do'' that?
* Ruffnut and Tuffnut fighting over a shield.
-->'''Tuffnut:''' Get your hands off my shield!
-->'''Ruffnut:''' There's like a million shields!
-->'''Tuffnut:''' Take that one, it has a flower on it! Girls like flowers!
-->'''Ruffnut:''' *whacks Tuffnut in the face with the shield* Oops! Now this one has blood on it!
** And then she hands back the shield and when the gronkle blasted them they are still fighting over the shield that she just proved she could take from him with little effort. You know then that they just fight 'cuz it's fun.
* "Your butts are getting bigger, we thought you were a dragon!" "NOT that there's anything wrong with a dragon-esque fig--" *punch*
* Tuffnut being a wuss with his injuries.
-->'''Tuffnut:''' [[MinorInjuryOverreaction Oh, I am hurt! I am very much hurt!]]
** Not all that Tuff is he.
* "I believe in learning on the job!"
-->'''Fishlegs:''' "I am seriously beginning to question your teaching methods!"
* Fishlegs is the Viking equivalent of a DungeonsAndDragons nerd.
* Gobber's tankard hand.
* "That was made from half your mother's [[GagBoobs breastplate]]."
** "And, uh...thanks for the the um...'breast-hat.'"
** Particularly funny, because Hiccup is stroking the helmet...and then jerks his hand away immediately after being told it was part of his mother's breastplate.
** HilariousInHindsight: [[spoiler:How did ''Valka'' fill that breastplate out?!]]
* When Hiccup [[spoiler:is found out by Astrid]] the deadpan tone Hiccup uses when he says "Duht-duh-duh, we're dead.". Gets even funnier when you realize that [[spoiler:Toothless is doing a picture-perfect copy of Hiccup's eyeroll, then stomps off on his hindlegs, apparently figuring to solve the problem himself.]]
* Hiccup imitating his father's Scottish accent.
--> "Excuse me, barmaid, I'm afraid you brought me the wrong offspring! I ordered an extra large boy with beefy arms, extra guts and glory on the side! This here, this is a talking fishbone!"
** And then Gobber chimes in with this little gem:
---> '''Gobber:''' It's not so much what you look like, it's what's ''inside'' that he can't stand!
*** Which results in [[http://cdn.hark.com/images/000/313/152/313152/original.jpg this]] face from Hiccup, before he delivers his CatchPhrase for the first time:
--> '''Hiccup:''' Thank you for summing that up.
* The following:
--> '''Gobber:''' Don't you... no, Hiccup! If you ever want to get out there to fight dragons, you need to stop all... this.
--> [gestures to all of Hiccup]
--> '''Hiccup:''' But you just pointed to all of me!
* Also:
-->'''Hiccup:''' Dad, I can't kill dragons.\\
'''Stoick:''' But you ''will'' kill dragons!\\
'''Hiccup:''' No... I'm really very extra sure that I won't.\\
'''Stoick:''' It's time, Hiccup...\\
'''Hiccup:''' Can you not hear me?\\
'''Stoick:''' This is serious, son. When you carry this axe [gives him an ax], you carry all of us with you. Which means you ''walk'' like us, you ''talk'' like us, you ''think'' like us. No more of [gestures to Hiccup] this.\\
'''Hiccup:''' [[RunningGag You just gestured]] to ''all'' of me.\\
'''Stoick:''' Deal?\\
'''Hiccup:''' [[DeadpanSnarker This conversation is feeling very one-sided]]...
* [[http://i219.photobucket.com/albums/cc257/eagleburdy/ROCKON.jpg THIS.]] Tuffnut's face. Took quite a few rewatches to spot--it's only on the screen for a split second, but hilarious.
* "Trolls exist! They steal your socks. But only the ''[[LiloAndStitch left]]'' ones. What's up with that?"
** Funny because you realized that Gobber only has one leg left. So OF COURSE his left socks go missing!
* The Teens [[spoiler: [[BigDamnHeroes Arriving on dragons]] in the final battle against the [[BigBad Red Death]]]] is both [[CrowningMomentOfAwesome awesome]] and funny. but the best part is Gobber's reaction to it.
--> '''Gobber:''' [to Stoick} Every bit the Bone-Headed, Stubborn Viking you ever were.
** And Stoick actually nods his head with an expression that says ''"well... can't argue with that."''
* After the romantic flight, Astrid smacks Hiccup, then kisses him, then runs off. Now, Hiccup's dumbstruck face after the kiss is funny enough, but what sells the scene is ''Toothless's'' reaction to the whole thing. After the smack, he gives Hiccup a look that says "dude, I ''know'', totally unfair". After the kiss, he wanders up behind Hiccup: "I think she liiiikes you, bud!" To which Hiccup's response is "What're you looking at?"

[[foldercontrol]]

[[folder: Legend of the Boneknapper ]]

* Pretty much the entirety, especially the increasing absurdity of Gobber's stories.
** Which includes one of the oddest BigDamnHeroes moment ever: A hammerhead yak riding a hammerhead whale. Summoned by Thor.
-->'''YAK:''' [[FastballSpecial DEPLOY THE YAK!]]
* Just as Gobber is being accused of lying/telling tall tales about the Boneknapper, another viking arrives to show the cause of the fire was....a pair of pants that have just been on fire.

[[/folder]]

[[folder: Gift of the Night Fury ]]

* In Gift of the Night Fury, Astrid finally understands how Hiccup has always felt.
--> '''Astrid:''' [[DidntSeeThatComing The eggs explode?]] *eggs explode* [[OhCrap The eggs EXPLODE!]]
** Even funnier since all the others immediately succumbed to CutenessProximity at the sight of the baby Gronkle.
** Or the exchange immediately preceding it:
-->'''Astrid:''' [[TemptingFate Wasn't this a great idea?]]
-->'''Fishlegs:''' Uh-huh! Everyone's gonna be so surprised!
-->''The first dragon egg explodes, blowing the door off the house it was in and sending the newborn Gronkle flying into Fishlegs' face, knocking him flat on his back.''
-->'''Snotlout:''' ''Surprise!''
* Also in Gift of the Night Fury, when Hiccup notices that a [[MadeOfExplodium Gronkle egg]] didn't get put into the water, he takes a step towards it. Look behind him, and you can see every single dragon present [[OhCrap hurrying for cover]].
** Followed by his comment about how it's lucky the eggs [[TemptingFate aren't hatching on Berk]]. Which is then followed by a GilliganCut to the scene listed above.
* [[NauseaFuel Yak Nog]].
* The little girl with the Terrible Terror! The Terror looked so indignant!

!! Second film

Go [[Funny/HowToTrainYourDragon2 here for the numerous funny moments in the sequel.]]