In a world full of fire-breathing beasts, Vikings, and sky-shattering battles, one dragon changed everything—not with brute force, but with big green eyes, curious head tilts, and a purr that could melt glaciers. How to Train Your Dragon introduced us to Toothless, a Night Fury shrouded in mystery and awe, who quickly became not just Hiccup’s best friend but one of the most beloved animated creatures of all time.
While Toothless is undoubtedly powerful—stealthy, fast, and capable of lighting up the sky with plasma blasts—it’s his adorable side that truly captured our hearts. Beneath the sleek black scales and lightning-fast reflexes lies a creature as catlike as he is ferocious, as loyal as he is mischievous. So, let’s dive into the many moments that made us go “aww,” clutch our chests, and replay scenes just to catch another glimpse of that precious dragon grin.
Here are Toothless’s cutest moments—the ones that made us fall in love with a dragon.
The First Big Blink: When Toothless Met Hiccup
Every great love story starts with a spark—and for Hiccup and Toothless, it begins not with fire, but with a stare. When Hiccup first stumbles upon the Night Fury he brought down, everything in the film’s tone shifts. We’re no longer watching an action-comedy about Vikings and dragons. We’re witnessing something fragile, something transformative. As Toothless lies wounded in a forest clearing, eyes flickering between fear and fury, Hiccup does the unthinkable: he shows mercy. And then… Toothless blinks.
That blink! It’s soft, tentative, almost questioning. In that single motion, DreamWorks accomplishes what a dozen lines of dialogue couldn’t: we see the fear in Tooth less’s heart, the cautious intelligence in his gaze, and the realization that this human boy might not be like the others. For a creature known as the “Unholy Offspring of Lightning and Death Itself,” this vulnerable eye movement is revolutionary. It’s the first sign that underneath the mystery and power, there’s a creature yearning for connection.
And let’s not forget the animation magic. The subtle twitch of the eye ridges, the way his ears flatten slightly, and the lingering look he gives Hiccup—all of it builds a moment that’s not just cute but monumental. This is the instant when a dragon and a boy stop being enemies and start becoming… something else. Friends, partners, kindred spirits. One blink, and everything changes. And we felt it in our chests.
The Forbidden Friendship: Fish Toss and Sand Drawings
If the first blink opened the door, the forbidden friendship scene burst it wide open—and melted our hearts along the way. In a moment of pure cinematic quiet, we see Hiccup and Toothless take cautious steps toward trust. Hiccup offers a fish like an olive branch. Toothless sniffs, eyes it suspiciously, and after a few comedic snorts and wiggles of his nose, takes a tentative bite. Then another. And another. Soon, he’s chomping away like a smug housecat who’s finally been served the right tuna.
It’s the rhythm of the scene that really gets you. There’s no dialogue. No instructions. Just two beings communicating through movement, mimicry, and an unspoken desire to understand one another. Hiccup draws in the sand; Toothless copies it, albeit in a wonderfully clumsy way. He stomps lines into the earth, not with finesse but with enthusiasm—and pride. And then, without prompting, he curls up beside Hiccup, close but not too close, like a shy pet testing the waters of affection.
This scene isn’t just cute—it’s intimate in the most innocent, pure way. Toothless’s goofy body language, the twitch of his tail, the way he narrows his eyes while watching Hiccup draw—it all reads as curiosity and cautious affection. It’s two souls speaking without a common language and finding, somehow, that they’re saying the same thing: “I see you. I trust you. I think we’re safe here.”
The sand drawings may be long gone by the next scene, but their emotional imprint stays with us forever.
The Drawing Scene: Toothless Gets Creative
One of Toothless’s most charming quirks is how he constantly tries to copy Hiccup—not to mock him, but to connect. And nowhere is that more evident than in the drawing scene. After watching Hiccup etch shapes into the sand, Toothless decides, “Hey, I can do that too!” He grabs a stick in his mouth like a proud artist, plants his claws like he means business, and starts scratching wildly into the dirt.
Is it a masterpiece? Not exactly. It looks more like something a toddler might create after six spoonfuls of sugar. But Toothless beams with satisfaction, looking at his messy, energetic artwork with the same joy Picasso might’ve felt unveiling Guernica. The animation here captures every nuance: the excited tail flicks, the squinty concentration in his eyes, and the way he throws his whole body into the task. He’s not just mimicking—he’s participating. He wants to be part of Hiccup’s world.
There’s something incredibly relatable about this moment. Haven’t we all tried to join in, to contribute, even if we don’t quite know what we’re doing? Toothless’s earnest effort reminds us that connection doesn’t require perfection—it just takes heart. His drawing may be scribbles, but the emotion behind it is crystal clear: “I’m with you.” And the fact that this moment ends with Toothless proudly standing over his creation, tail wagging and eyes bright, is just the frosting on the emotional cake.
Toothless Learns to Fly (With a Buddy System)
Watching Toothless relearn how to fly is equal parts inspiring and downright adorable. After Hiccup crafts a prosthetic tail fin to replace the one damaged during their initial encounter, the stage is set for one of the most heartwarming training montages in animation history. But this isn’t just a boy teaching a dragon to fly—it’s a boy becoming part of a dragon’s flight. It’s bonding at 30,000 feet, and it’s the definition of cinematic charm.
The early attempts are anything but graceful. Toothless, who once ruled the skies, now struggles with balance, control, and the indignity of depending on a human co-pilot. He spins. He crashes. He flaps furiously. And every time he flubs a landing or overshoots a dive, his facial expressions are priceless—equal parts confused, frustrated, and dramatically annoyed. You can practically hear him thinking, “Ugh, I used to be majestic!”
But what makes this sequence so irresistibly cute is the joy that slowly creeps back into his face once things start clicking. There’s a moment—small but unforgettable—when they hit the perfect rhythm mid-flight. The wind rushes past, the sun breaks through the clouds, and Toothless throws his head back in pure delight, letting out a gleeful roar. It’s the sound of freedom, of rediscovery, and of shared success.
Hiccup holding the handles, adjusting the gears, and learning to trust Toothless is already powerful—but Toothless trusting him back, allowing this fragile human to guide him through the skies, is what makes our hearts swell. It’s not just a flying scene. It’s a falling-in-love-with-freedom scene, and it’s cute in the kind of way that makes you grin so hard it hurts.
The Purring and Ear Wiggles
If dragons could win “Most Likely to Be Mistaken for a Housecat,” Toothless would take the crown, claws down. And nowhere is that more obvious than when he starts purring. Yes, purring. Not roaring. Not growling. Not snorting smoke. Actual, honest-to-Odin, contented purring. It’s the kind of deep, rumbly sound that makes you want to curl up next to him and never leave.
Toothless’s purring is often paired with his signature ear wiggles—a behavior so disarmingly cute that it deserves its own montage. When he’s curious? Wiggle. When he’s excited? Wiggle-wiggle. When he’s confused by Hiccup’s latest invention? Triple wiggle with a head tilt. These expressive ears are basically an emotional barometer, flopping and perking like antennae tuned to the frequency of our hearts.
There’s a moment where Hiccup scratches just under Toothless’s chin and Toothless closes his eyes in bliss, melting into the touch. It’s such a subtle scene, but it tells us everything: this fierce dragon doesn’t just tolerate humans—he loves them. He craves affection. He seeks out companionship. And the fact that his way of showing it is through catlike chirps, thumping tail wags, and lazy rolls onto his back? That’s peak dragon cuteness.
The animators infused Toothless with an uncanny blend of predator and pet. The result is a creature who can level a mountain one minute and snuggle up in your lap (well, hypothetically) the next. And every purr, every wiggly ear twitch, reminds us that even legends need a good cuddle now and then.
Toothless and the Tail Fin Gift Scene
If there’s one scene that perfectly blends emotional depth and dragon delight, it’s the moment in The Hidden World when Hiccup gives Toothless a brand-new tail fin—one that allows him to fly on his own. No more gears, no more levers. For the first time since their bond began, Toothless has the freedom to soar solo. And the look in his eyes when he realizes it? That wide-eyed, slow-blinking gaze of gratitude and wonder? It’s pure animated gold.
Toothless approaches the gift cautiously at first, sniffing it as if it might explode. But as realization sets in, his posture straightens, his eyes brighten, and you can see the happiness bubbling up in him. Then comes the moment he lifts off—graceful, powerful, effortless. He climbs into the clouds, loops through the sky, and for the first time, he isn’t tethered. But he isn’t leaving, either. He flies because he can, not because he wants to get away.
And then the cutest part: he turns mid-flight to look back at Hiccup. That glance isn’t just a check-in—it’s a thank you. A moment of, “You gave me my wings. I won’t forget.” That tiny motion says more than any speech ever could.
This scene is cute because it’s Toothless at his most honest. Free to be wild but still tethered by love. It’s the animated equivalent of a dog off-leash who still looks back to make sure you’re keeping up. Only this dog can break the sound barrier.
The Courtship Dance: Toothless Meets the Light Fury
Toothless may be the last of his kind, a sleek, fearsome Night Fury with the speed of lightning and the brain of a tactical genius—but when he meets the Light Fury, he becomes the dragon version of a nervous middle schooler at a school dance. What follows is one of the funniest, most endearing, and unexpectedly relatable scenes in the entire franchise: the courtship dance.
The build-up is already adorable. Toothless sees her. He freezes. He tilts his head. He chirps. And then, realizing he must impress her, he launches into full “look at me” mode. He puffs his chest, flares his wings, and then—completely flubs his first move. He flops over. His legs kick wildly in the air. His wings get tangled. The Light Fury watches, unimpressed and vaguely horrified, while Toothless scrambles to recover, acting like it was all part of the plan.
But does he give up? Never. That’s part of what makes the scene so endearing. Toothless doesn’t know what he’s doing, but he wants to impress her. So, he commits—stomping, swaying, flapping his wings like he’s seen too many bird documentaries. He even draws in the dirt again, trying to appeal to her with art (remember his earlier sand doodles? Clearly, he considers himself a creative). And though most of his efforts are met with confusion or disinterest, he keeps trying, driven by sheer, goofy affection.
This scene is animated physical comedy at its best. Toothless’s awkward flailing is both hilarious and heartbreakingly pure. We see a creature capable of leveling armies reduced to clumsy antics in the name of love. And the best part? It works. Eventually, the Light Fury softens. She sees the heart behind the chaos. And so do we.
The Snuggling Scene in the Hidden World
Once Toothless and the Light Fury finally connect, we get one of the quietest, most magical scenes in the trilogy—and one that might just be the coziest in dragon history. When they arrive at the Hidden World, a glowing subterranean paradise of bioluminescent wonder, we see Toothless in a completely new light—literally and figuratively.
As he glides through the glowing caverns, his awe is palpable. He’s wide-eyed, tail swishing with curiosity, ears twitching with delight. The Light Fury nudges him forward, encouraging him to explore, and for once, Toothless isn’t the guide—he’s the guest. Watching him tiptoe around glowing crystals and fluttering bugs is like seeing a child experience snow for the first time. It’s not just adorable—it’s pure.
Then comes the snuggle. Under a canopy of glowing vines, Toothless curls up next to the Light Fury, letting out a soft, contented sigh as he nuzzles close. His eyes droop. His breathing slows. His wings tuck gently around her like a blanket. This is a creature who has fought wars, lost friends, and flown faster than sound—yet here, in this moment, all he wants is closeness.
The intimacy of the scene speaks volumes. There’s no music, no chatter—just the quiet hum of a magical world and the gentle rise and fall of two dragons finding peace together. Toothless has always been expressive, but here, he’s vulnerable in the most beautiful way. It’s not just cute—it’s soul-soothing. The kind of scene that makes you exhale slowly and think, “This is what happiness looks like.”
The Goodbye: Bittersweet and Beautiful
Few animated farewells have hit as hard as the one in The Hidden World. After years of fighting side by side, flying together, and forming a bond deeper than most human relationships, Hiccup realizes it’s time to let Toothless go. And Toothless—faithful, loving, and visibly torn—understands.
The moment is wordless but overflowing with emotion. Toothless approaches Hiccup, looking unsure, almost like he’s asking, “Is this really it?” When Hiccup reaches out, Toothless lowers his head, gently bumping his forehead to his friends in their signature gesture of connection. It’s a hug, a handshake, a farewell—and a thank you.
But it’s not a dramatic, slow-motion goodbye. It’s quiet. Reverent. The way Toothless lingers, his eyes shimmering with sadness and gratitude, is heartbreakingly honest. He knows it’s time to move on. He knows the Light Fury needs him, and that Hiccup needs to step into adulthood. Still, he doesn’t turn away until the very last second—until he’s sure they’re both okay.
What makes this scene so powerful is that Toothless doesn’t roar or cry out. He doesn’t throw a tantrum. He simply looks back. That glance, that lingering gaze from dragon to rider, says more than any farewell speech ever could. It’s the look of someone saying goodbye to a piece of their soul. And yet, it’s filled with hope. A hope that this isn’t the end. A hope that love doesn’t fade, even across great distances.
The Reunion: “This is Toothless.”
Years pass. Hiccup is older, wiser, a husband and a father. And yet, the love he shares with Toothless remains unchanged. When he sails to the edge of the world with Astrid and their children to find the Hidden World once more, the tension is delicious. We’re waiting. We’re hoping. And then—he appears.
Toothless, sleek and regal, bursts through the clouds like a comet. He hasn’t aged a day, still a gleaming shadow against the sky. But his face is different. Softer. Warmer. And the moment he locks eyes with Hiccup, it’s like no time has passed at all.
The reunion is pure magic. Toothless lands, cautious at first. He stares. He sniffs. And then—recognition. His eyes light up, his posture shifts, and he bounds forward like an overgrown puppy reunited with his favorite human. He chirps. He nuzzles. He wraps his wings around Hiccup in a tender, dragon-sized hug. It’s pure, unfiltered affection.
The moment becomes even more touching when Hiccup introduces his children: “This is Toothless.” And Toothless, gentle and curious, lowers his head to greet them—passing on his trust, his love, and his legacy to the next generation. It’s the final beat in a story that began with fear and ended in unconditional friendship.
It’s not just cute—it’s perfect.
Why Toothless Isn’t Just Cute—He’s Iconic
Toothless didn’t become one of the most beloved animated characters of all time because he’s just cute—though, let’s be real, he’s ridiculously cute. He became iconic because he’s real. Every twitch of his tail, every awkward stumble, every joyful roar, and every purring snuggle feels authentic. He’s a fully realized soul, brought to life through animation that captures both the majesty of dragons and the charm of the family pet.
He shows us that strength can be gentle, that vulnerability isn’t weakness, and that love—be it between friends, family, or fire-breathing legends—is what makes life worth flying for. Toothless doesn’t speak with words, but he’s said more to our hearts than most movie characters ever could.
So if you ever find yourself needing a reason to smile, to believe in the magic of connection, or just to say “awwww” on repeat, look no further than the Night Fury with the gummy grin and the biggest heart in the sky.
