One of my most favourite, yet absolutely heart wrenching headcanons that keep me awake at night, is that Hiccup missed Viggo after his death.
Because here’s the thing. Apart from the fact Viggo sacrificed himself for Hiccup, Toothless and their cause, and apparently grew to understand and respect the creatures he once sold and killed, he was the only antagonist who truly ever matched Hiccup. The only one who could really keep up with his intellect, strategies, ways of thinking, and challenge him himself, so much they became obsessed with each other.
And I think for someone like Hiccup, who has always felt like he didn’t quite fit even among his own people, having an opponent who had the mental capacity to comprehend all of Hiccup (and being pretty much the only one), was both exhilarating and terrifying. You can come at me for saying this, but Viggo held much more respect for Hiccup’s ingenious mind than the Riders and Berkians ever did.
I personally don’t think it went as far as liking Viggo as a person. But it was about the strange way an enemy can become a mirror. And once the mirror broke by Viggo’s demise, Hiccup caught himself unconsciously staring at the pieces with a painful realization. Realization, that he misses that mind, equaling his own, that challenge, that presence and maybe if he ever let himself think for too long, he missed Viggo himself.
