HTTYD Fanart Gallery #3 – Theme: Funny Hiccup & Toothless Moments

Hiccup eating regurgitated fish, scene from HTTYD 1.
Food Gift: DreamWorks A.

The movies had a good deal of fun moments between the Vikings and dragons, and the long-running TV series had quite a lot more.

Hiccup almost completely buried in fish, and Toothless looking at him smugly.
MEGA Food Gift: DreamWorks A.

When the Vikings and dragons in the TV series weren’t learning to work together, or risking life and limb to rescue other dragons, they usually had fun goofing off or were out discovering new things in the Barbaric Archipelago.

Hiccup and Toothless both standing on 2 feet and looking at each other.
Two Bros. DreamWorks A.

These relaxed, fun and adventurous situations have surely helped inspire funny fanart as well.
Today’s blog post is all about fanart showing fun moments and adventures with Hiccup and Toothless.

Hiccup and Toothless walking on a log across a river.

Click on a picture to see it pop up in a “lightbox”. Pictures are posted in no particular order. (Featured image: Untitled – by Sharkie 19)

Hiccup and Toothless – by Forkandspoon00

Toothless staring at viewer with funny look on his face, Hiccup is laughing next to him.That moment, when your best friend pulls a goofy smile for the camera.


Hiccup – by hiraco

Toothless giving reluctant Hiccup a hugWhat’s the matter Hiccup, is there such a thing as too many Toothless hugs? Impossible!


Happy Birthday Hiccup – by Sharkie 19

Toothless want all of Hiccup's birthday cake, not just five piecesListen to Hiccup, Bud – all that sugar will rot your teeth!


Toothless and Hiccup – by TsaoShin

Toothless sharing his fish with Hiccup, by putting the fish on top of Hiccup's head.Uhm, Toothless… I think Hiccup prefers his food gifts cooked, not raw!


Making Outfits – by Sharkie 19

Hiccup making a woman's dress, Toothless watching and doesn't quite understand what's going on.Hiccup sure does some fine stitching. Toothless shouldn’t be so surprised – his saddle looks great!


When I saw Toothless popcorn bucket – by Kadeart0

Toothless sitting in a tub of popcorn, as one would sit in a spa.Hey Girl, I popped this corn for two! (The pickup lines are almost endless.)

Hiccup eating popcorn from a Toothless-shaped tub, Toothless see this and is shocked.Hey, Toothless! It’s delicious, you want some?


Snowman Toothless – by Allagar

Snowman Toothless - by AllagarSo, if Hiccup makes a Toothless snow-dragon, then will that make him a Light Fury?


A Very HTTYD Halloween – by TsaoShin

Hiccup and Toothless Trick or Treating.A Viking and his Dragon… Trick or Treating as Pokemon trainer and Pokemon. I’d give them all my candy, just to keep those two on my doorstep a moment longer.


Hiccup and Toothless Investigate Something – by Little Ampharos

Hiccup and Toothless hiding and peering from behind a log, both looking at something.Did they just spot an eel with legs? That would surely freak out both dragon AND human!


Night Fury Invasion!!! – by Kadeart0

Hiccup being overpowered by many playful baby Night Furies.Oh, so it was just a wild pack of baby Night Furies! Don’t be like that, Hiccup – 99.9% of fans agree you can NEVER have too many playful Night Fury babies!


Tasty Fish – by Majime

Hiccup eating fried fish, and Toothless wants some or all of it.Hey, Hiccup – you have to share your fish too!


Toothless Being Toothless – by MimiforArt

Toothless chasing a glowing insect with Hiccup on his back, who can barely hold on.Glowing beetles: what dragons used to chase, before laser pointers were invented! Is it me, or does that bug look like he’s already endured a few hundred encounters with playful dragons?!


In my next post, I’ll start showing some of my favourite Astrid and Stormfly art!
Toothless... I mean a CAT, chasing laser pointer dot.I’ve also got some more funny pictures for posting later, once Toothless has finished chasing his laser dot bug. (In a couple of weeks, or so.)
If you have suggestions, would like to recommend some art or submit your own, feel free to get in touch!

In the meantime, you can also leave comments on this post below:

By Beinir (Ben) Madbear - Hairy Fansite Founder and Owner.
Passionate dog person, but also likes cats and animals in general. Web developer and online producer, who became a “How to Train Your Dragon” fan after coming across it on TV back in 2018.

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