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English
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Published:
2026-02-14
Updated:
2026-02-14
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1,791
Chapters:
2/?
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2
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34

sisyphean endeavour

Summary:

After surviving the fall of his empire and the events of triple cross, Viggo Grimborn retreats to a secluded island, living in solitude as a way of atoning for his past.

But when the Riders and Berk’s leaders arrive to arrest him for allegedly capturing dragons, they uncover a far worse threat: Drago Bludvist is back, and he’s more dangerous than ever.

As the Riders join forces with Viggo, who must prove he’s no longer the man he once was, the lines between enemy and ally blur. In the fight to stop Drago and protect the dragons, a former villain will find his place among the Riders, but will Berk trust him enough to stand by his side?

OR:

The story of how a group of stubborn vikings turn Viggo into something far greater than a former 2-bit crime lord

Chapter 1: burning anxiety

Notes:

Hello everyone and welcome to my newest fic- Sisyphean Endeavour!! I decided to write this because after rewatching triple cross, I decided I wanted to read an AU where Viggo becomes a rider. Unfortunately, I do not like Vigcup very much, so there weren’t too many fics for me to read. Anyway, let me just get started with a few warnings!

1) As for warnings, I think this is very much teen and up. There won’t be anything too troubling, but if there is I’ll mention it in the chapter notes (beginning)

2) For posting schedule, I don’t have one but I’m really into HTTYD atm so this will probably be updated fairly frequently!

Anyway, with that out of the way, I hope you enjoy this fic!

(See the end of the chapter for more notes.)

Chapter Text

Hiccup’s hands clenched and unclenched at his side, a repetitive motion he often did when he was deep in thought.

It had all been too easy.

First, Viggo had betrayed Krogan and Johann, sacrificing himself in the process.

Then, the riders had managed to take the two down while they were in a state of disrepair. 

Hiccup was naturally a worrier, and he understood that, but he knew full well this had all been far too easy. Had that truly been the final battle? Would Berk return to living peacefully once more? Perhaps. But still, that gnawing feeling continued to bloom in his chest.

Unfortunately, as Snotlout had so rightly put it, Hiccup was always right.

Just then, a high pitched dragon scream erupted through the Edge, and a thudding right outside the clubhouse had Hiccup up and running, tearing the door back to see what had happened.

In front of him lay a skrill. Not just any skrill, however. This was the skrill. Hiccup would notice its purple scales any day of the week.

Perhaps the more concerning part of all of this was that Viggo was on top of said dragon, using one hand to support himself as he slowly climbed off of it.

Before Hiccup had truly had time to process, the other riders were behind him, weapons drawn. The dragons further supported them, flames already brimming in their mouths.

“Hi-ccup…” His voice hitched as he took another weak step forward, the skrill still seemingly supporting most of his weight. As he stepped forward, Toothless snarled, preparing a plasma blast.

“Woah, bud… Hold on.” Hiccup said quickly, gently pushing Toothless’ head away from its line of fire, eyes focussing entirely on Viggo. Despite subtle, it was clear from the ridges in his forehead that he was in pain. The way his body seemed to tremble also made it clear.

“Hold on? Hiccup, that’s Viggo! Like, the Viggo that tried to kill us multiple times. We should just get rid of him and be done with it.” Astrid commented, axe raised, poised to strike.

Viggo seemed to let out a slight chuckle as he raised one hand.

“I’m not here… for a fight.” He replied calmly, wincing as he spoke.

“You can’t not be here for a fight!” Snotlout replied snappily as Viggo seemed to nod absently, eyes flicking to Snotlout before returning to Hiccup.

“Quite right.” He hummed, taking another weak step forward. This time, his weight seemed completely off balance, and Hiccup’s eyes widened as the older man collapsed to the floor with a weak grunt.

The skrill let out an undignified screech, head lowering to examine Viggo.

The man had several arrows stuck firmly in his back, and Hiccup noted that they were clearly dragonroot. While the effects weren’t quite so bad on humans as they were to dragons, they were still unfavourable indeed.

Hiccup took a few quick steps forward, crouching down beside Viggo and watching him closely for a moment.

“You see now the… rather precarious situation I’m in, yes?” He muttered from his position on the floor.

“I do. Fishlegs, you think you can treat him?” Hiccup asked over his shoulder, still not taking his eyes off of Viggo.

“Yes, but… Are you sure it’s the right thing to do?” Fishlegs asked carefully, voice low, “I mean, he’d go to any lengths to win. This could just be another one of his tricks!” He spoke, voice getting more urgent.

“And if it’s not a trick? Viggo could be a great rider-” Hiccup began, getting swiftly cut off by Astrid.

Rider? Hiccup, you can’t be serious! He’s killed hundreds of dragons!” She exclaimed as Hiccup exhaled, looking back down at the man. He was seemingly now passed out on the floor in a pool of his own blood.

“Okay, well… we’ll cross that bridge when we come to it. At the very least, he’ll be a good source of information. Fishlegs, let’s get to work with healing.

‘Will he be okay?’ The skrill’s tongue clicked in a familiar language as Hiccup nodded slowly. He had become accustomed to dragonspeak over the last few years, and while the skrill’s dialect seemed to be thicker than what Hiccup was accustomed to, he was still able to translate.

“If we get a move on, yes.” He nodded reassuringly, beckoning Toothless over to help pick up and carry Viggo into the clubhouse.

As soon as they were inside, Fishlegs and Hiccup both immediately got to work on healing the heavily injured Viggo Grimborn that lay unconscious in front of them.

Notes:

And we’re off! Thanks for reading and see you next time!
- Lucy!!