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You never cease to amaze me, bud. Thank you. [src]
  — Hiccup  

Hiccup and Toothless have a very close bond that has gotten stronger as the franchise continues. Both Hiccup and Toothless lead Berk as leaders of their respective species. They first met in the first film of the franchise, and have been featured in every show and film since.

First Meeting and Forging a Bond

Fateful Shot

That fateful shot...

Hiccup's first encounter with Toothless is fleeting. Hiccup aims his catapult and is looking for something to shoot at---specifically, the Night Fury---when Toothless flies across and is briefly silhouetted against the starry night sky. Hiccup roughly gauges where the dragon would be in his flight trajectory before shooting, and successfully strikes the dragon mid-flight, as evidenced by the roar and howl he emitted while visibly plummeting toward the ground. Though Hiccup was ecstatic at having finally shot down a dragon, and a Night Fury no less (a species he had himself aspired to take down for a while), no one else was present to witness his success, besides a less-than-friendly Monstrous Nightmare, much to Hiccup's disappointment and imminent horror.
First Sight

First sighting

He later goes in search of the dragon he shot down, experiencing a lack of success that he vocalizes in frustration, right before he finally stumbles upon his first clue of where the dragon fell. Approaching the crash site carefully, albeit in some haste, he follows the trail the Night Fury made on the ground during the crash landing before suddenly spotting the dragon's sprawled, restrained form over a mound and ducking in shock. In a series of tense moments, he slowly works up the courage to first expose himself slightly to look at the scaled beast, before slowly approaching it after drawing his knife and defensively moving toward the incapacitated reptile. After peering around a rock he'd hidden behind that obscured proper vision of the Night Fury, he realizes that the bola had completely immobilized the dragon (who initially appears dead or unconscious), and his ecstasy finds him once again as he believes his tribe will finally think highly of him, and take him seriously. In his celebratory moment, he places his foot proudly on the Night Fury's shoulder while proclaiming that he had "brought down this mighty beast", before the dragon, still very much alive and conscious, shrugs him off with a loud, somewhat pained grunt, putting the boy on the defensive again as he realizes that the dragon may yet pose a threat. As he brings his knife to bear once more, he cautiously approaches once again, and this time finds the dragon peering at him out of the one eye facing him. 
It Runs In The Family

"Ah, it runs in the family..."

The timid teen nervously looks back at the dragon, before slowly working up and building up the courage and bloodlust necessary to use the knife on his catch, telling the waiting reptile (and mostly himself) that he would cut out his heart and take it to his father, and that he was a Viking, feeling the need to repeat the last point in a more aggressive tone before he raises the knife over his head. He looks back at the dragon one last time; the beast has not taken his eye off him. Hiccup closing his eyes, raises the knife over his head and grits his teeth once more. The Night Fury also closes his eyes, letting his head drop in despair as he awaits the killing blow... which never comes.

Unable to bring himself to slay the beast, Hiccup looks at the dragon, still awaiting his fateful end, before expressing disappointment in himself at having even shot him down in the first place, realizing that he didn't have it in himself to kill him. As he walks away dejectedly, he pauses and looks back at the downed beast, realizing how helpless he was in his shackles, still awaiting his end. The Night Fury's eyes suddenly open as he hears a cutting sound to his side, and looks to his left as he realizes that Hiccup is cutting away his restraints. His bound limbs come free, and in an instant he pounces on the boy, pinning him to the rock behind by his neck and chest, sending the latter into a panicked state as he looks up at the dragon, who gazes back sharply through narrowed pupils as he regards his former captor. As the intimidated teen squirms in terror, the dragon looks on for a second more, rears up and takes his foot off the boy's torso as he emits a loud, fearsome roar right in his face, turns, and leaps out of the clearing and into the undergrowth, attempting to take flight as he does, but crashing into a rock and a few other things as he fails to do so, disappearing from sight altogether. A very shocked and spooked Hiccup turns to make his way back (but not before comically collapsing once out of sheer relief and recovery from his terror).

Night Fury Scale

Hiccup's first souvenir...

The next morning, following the teens' first dragon-slaying class, the course of which very nearly saw Hiccup blasted to death by the arena's Gronckle before being saved by Gobber, the students (and Hiccup in particular) are warned by the blacksmith that a dragon will always, always go for the kill. Later, Hiccup revisits the site of the Night Fury crash, picking up one of the bolas on the ground as he wonders out aloud why the dragon he freed didn't do the same. His curiosity getting the better of him, he makes his way into the forest, in the direction the dragon disappeared in, eventually finding himself in a niche opening out into a large, secluded, naturally formed pit-like clearing with high rock walls and a lake in the middle of it. He looks in and sees no sign of the dragon inside, remarking in disappointment that it was stupid to even try and find him again, before some black dragon scales on the floor of the niche draw his attention, and he crouches down to look at them. As he picks one up and examines it, the dragon suddenly bursts upward from the floor of the pit (previously concealed by the peripheral blind spot of the niche) toward the top of the wall, right in front of the opening the boy is in, causing him to fall backward in shock and fear. The Night Fury attempts to scramble onto the top of the wall but slides back down as he haplessly claws at the rock, unable to find purchase, before attempting to avert a hard, awkward landing by leaping off the rock and pivoting to glide back toward the ground, crashing nonetheless as he nears it. The inquisitive teen moves out of the niche and jumps onto a sloping rock platform just below it (nearly sliding off and into the pit in the process), trying to get a closer look.

Hiccup takes the opportunity to make a quick (and surprisingly detailed) sketch of the dragon in his book as he observes him attempting to take flight and escape the clearing several times, each attempt culminating in failure. It is then that the boy wonders why the Night Fury doesn't simply fly away, realizing as the dragon fires off a shot into the ground nearby in exasperation, that one of the reptile's tail fins is missing, likely lost during his crash landing in the forest. He accordingly smudges out the corresponding tail fin in his sketch, surmising that both fins must be required in order for the creature to achieve steady flight. This theory appears confirmed as the dragon attempts flight once more, his tail stalling out and ruining his flight-form mid-air, dropping him onto the ground once again. As the Night Fury lays there exhausted and frustrated, a fish flops up and back into the lake nearby, and the dragon gets up to try and catch himself some food. He plunges his face into the water, hoping to snag one of the fish swimming around near the surface in his jaws, but fails to do so. Hiccup, watching from above at the other end of the pit, feels sorry for him, and accidentally drops his stylus into the clearing. It bounces off some of the rocks, catching the reptile's attention, and causes him to look up. He recognizes the boy, and they both warily look at one another out of curiosity.

Book of Dragons

First Snoggletog Together

Like any other scene, Hiccup and Toothless' friendship always stand out. They are seen to fly with each other, soaring the Berkian skies. Hiccup also cares a lot for Toothless and as well as the dragon to his rider. Hiccup even got a little sorrowed for Toothless because he couldn't fly with the other dragons to the hatching grounds, so Hiccup built him a tail that would help him fly on his own. Seeing Toothless fly off after receiving the tail, Hiccup thought he was not going to back but instead Toothless used is to retrieve his rider’s helmet, which got lost somewhere in the middle of the vast ocean.

Learning to Work as a Team

TerribleTwos-Hicctooth2-104

Hiccup and Toothless glare at each other

In the episode "The Terrible Twos", Hiccup learns to listen more attentively to what Toothless tries to tell him. Hiccup finds a baby Typhoomerang in the woods named Torch. He also brings him home and shares Toothless' food and bed with him. Toothless behaves strangely, which Hiccup interprets as jealousy and wrongly attributes some broken items and a fire to Toothless. Until he can figure out a way for Toothless and Torch to get along, Hiccup leaves Toothless in the Cove where he can't leave. In truth, Toothless does display some jealousy due to Torch's juvenile antics such as eating his food. Ultimately though he was attempting to get Torch back to his distressed mother, and curtail her destruction of the Berk forest trying to find her baby. Ultimately Hiccup and Toothless are reunited and Hiccup apologizes for misunderstanding his dragon.

IDWT-Hicctooth2-113

Leaving Toothless on Dragon Island

Hiccup is forced to leave Toothless on Dragon Island along with the rest of the dragons in "In Dragons We Trust". The dragons are framed by Mildew for various incidences of property damage, including the destruction of the Berk Berk Armory, which Toothless is blamed for. At this destruction, Stoick deems the dragons as too dangerous to stay on Berk. Hiccup does voice concern, but doesn't fight it due to lack of evidence. He and the Riders leave the dragons. Hiccup's and Toothless' good-bye is especially poignant, as Toothless cannot fly without Hiccup and the two repeat the iconic hand-to-nose bonding moment.

The following episode, "Alvin and the Outcasts", finds Toothless and Hiccup each pining away for the other. With the dragons and weapons gone, the Berk is vulnerable and gets attacked by Alvin the Treacherous, who is looking for the 'Dragon Conqueror'. Hiccup reveals himself, and tricks Alvin into taking him to Dragon Island where the dragons were banished to. The pair are reunited, and the dragons proceed to demonstrate just how valuable they are around Berk and defending it.

While trying to bring his father around to the 'Dragon Way' in "How to Pick Your Dragon", Hiccup lets Stoick use Toothless to fly around Berk on. Toothless doesn't protest but gets very worn out by Stoick's rough hand and many chiefly duties. Hiccup apologizes to Toothless and also exhibits some jealousy toward his father for taking 'his dragon'.

Dragons: Defenders of Berk

This section requires expansion.


Dragons: Race to the Edge

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A Test of Friendship and Leadership

Hiccup and Toothless' friendship never goes unnoticed in this film. They treat each other like brothers, and they even tease each other just for fun. Hiccup cares for Toothless deeply, and Toothless loves his rider with all his heart, much like every rider to their dragon, although Hiccup and Toothless' relationship can go beyond that. Toothless is seen to save Hiccup a couple of times in this film. And it is also Hiccup who brought Toothless back to his right mind when he was in control of Drago's Alpha, and the only way to describe this is the strength of their friendship. Although, one scene in the movie showed Hiccup angry and sorrowed about Toothless, pushing him away and telling the dragon to back off. But only because Toothless was controlled by the Alpha and killed Hiccup's father, Stoick the Vast.

How to Train Your Dragon: The Hidden World

This section requires expansion.


Graphic Novels

Burning Midnight

The Serpent's Heir

Hiccup and Toothless are still learning about the burden of becoming leaders. When Calder plans on killing Toothless to obtain his wings, Hiccup and the other Riders manage to prevent the madman from doing so.

Dragonvine

During the events of Dragonvine, Toothless gets entangled and poisoned by dragonvine, a plant deadly to dragons. Toothless immediately becomes ill, and Hiccup soothes him, in tears that he might lose his friend. Fortunately, the Silkspanner dragons are both immune to dragonvine and can remove or inactivate the toxin in others. A few babies swarm over Toothless, eating away the dragonvine and healing him.

Quotes

Films and Shorts

Thank you for nothing, you useless reptile. [src]
   
Astrid: "Hiccup, we just discovered the Dragons' Nest. The thing we've been after since Vikings first sailed here. And you want to keep it a secret?! To protect your pet dragon?! Are you serious?!"
Hiccup: "Yes."[src]
   
I couldn't kill him, because he looked as frightened as I was. I looked at him, and I saw myself. [src]
   
If something goes wrong... just make sure they don't find Toothless. [src]
   
Bad dragon! Very bad dragon! You scared me to death. Don't ever stay away that long again, and what is in your mouth?
(Toothless puts Hiccup's now spit covered helmet on his head)
Yeah, you found my helmet. What-hey! You found my helmet! That's where you've been? Buddy, thank you! You are amazing!
[src]
   
That year, I gave my best friend a pretty great gift. He gave me a better one.
  — Gift of the Night Fury - referring to Toothless choosing Hiccup's friendship over freedom.  
Toothless didn't just become my friend. He became the friend who gave me my purpose. [src]
   
You never cease to amaze me, bud. You know that, right? [src]
   
"What do you think, bud? You wanna give this another shot?"
(Toothless groans skeptically)
"Toothless! It'll be fine."
[src]
   
"Oh, come on. You wouldn't hurt a one-legged—AHH!"
(Toothless laughs)
"You're right! You're right! You win! You win!"
[src]
   
"He's down! Ah, and it's ugly! Dragons and Vikings, enemies again, locked in combat to the bitter..."
(Toothless pins Hiccup, who moans in mock pain. Toothless then licks him repeatedly)
"Ugh! C'mon!"
(jumps to his feet and wipes the drool off his clothes)
"You KNOW that doesn't wash out!"
(Toothless laughs and Hiccup playfully flicks the excess drool at him) [src]
   
Don’t worry, bud. I’m not gonna let anything happen to you. I promise. [src]
   
Toothless! You really had me worried there, bud. [src]
   
It wasn't your fault, bud. They made you do it. You’d never hurt him. You’d never hurt me! Please. You are my best friend, bud. My best friend. [src]
   
We can do this. You and me. As one. [src]
   
Hiccup: "He's challenging the Alpha!"
Valka: "To protect you."[src]
   
I will never give him up. [src]
  — Hiccup, to Grimmel  
It's you and me, bud. Always. [src]
   
You're right bud, its time. You've looked after us long enough, time to look after yourself.
   


Cast

Toothless is Hiccup's best friend, y'know, not to take away from any of the humans in his life, but he just, they have a symbiotic relationship. They need each other. And despite the fact that they're two completely different species, they have more in common with each other than they do probably with their respective species. They're both kinda odd birds, outcasts, and they both had some work done. There's no Hiccup without Toothless.
  — Jay Baruchel on Hiccup and Toothless[1]  


Trivia

  • Hiccup and Toothless' relationship is close because Toothless is the same age as Hiccup, as revealed by Valka in the second film.
  • Ever since the first film, the two share many things in common.

References

  1. How To Train Your Dragon 2: JAY BARUCHEL "Hiccup" On Set Movie Interview. (Date Posted - May 16, 2014). YouTube. Retrieved August 6, 2018.

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