Welp, probably one of the craziests things I have ever done in my existence... and that is to propose someone like this here, but first of all, bear with me and hear me out, you have already read the title... but yeah, hear me out.
What's the Work?
New Panty & Stocking with Garterbelt is the continuation of the original series of Panty & Stocking, a series with a lot of adult humor, sex, sweets, fallen angels and a bunch of weird stuff that makes this show pretty funny. Following the story of the fallen angels Panty and Stocking as they try to get enough heaven coins to get back to heaven by killing ghosts born of the pain and hatred that occur in that world, while also having epic appearances of demons, a weird priest and even gods.
But let's forget about all of that, as not only this series is too comedic for anyone to count as PE, but that it suffers from a bunch of comedic sociopathy from part of the protagonists... unless we count one non-canon and weirdly serious episode.
Lord of Kokan the Great, contrary to the majority of episodes of this series, usually categorized by a bunch of jokes, comedy and sex jokes, this episode goes into a completely non-canon episode in a completely different setting, more similar to Seinens or Shonens like for example something like Berserk or Conan the Barbarian (after all, this episode its inspired by them), following a pretty serious story which is protagonized by our usual protagonists, but with pretty different portrayals and personality, which makes them more serious, with Panty being more of a serious warrior seeking for revenge, Stocking is a dragon that ends up allying with our protagonist in his quest for revenge and Briefs is an elf that got his village attacked by some monsters but rescued by Panty.
In this weirdly serious episode, there's a very vile being responsible of all.
Pretty fucked up
Who are Scanty and Kneesocks/The Two-Headed Demon? And what did they do?
Yep, you are reading this right, a serious pure evil version of the demon sisters Scanty and Kneesocks (who are not really called like this in this series), but anyways, let's explain.
The Two-Headed Demon is the main villain of this story, who years ago attacked Panty's village and burned it all down, killing his relative (who is Garterbelt, and yeah, in this story Panty is a guy), in her dragon form, something that she enjoyed a lot. All of this destruction and death is implied to be to attain two dragon eggs that the village had, which the demon planned to use to empower herself, only for the Panty kid to attack her, making her drop the eggs and end up with big scar in her abdomen, as the attack was done with a pretty sharp item, being one of the tooth of the dragon. All of this forced the demon to escape and continue with her plans later on.
Years later, Panty grew into a muscular and completely serious warrior, fighting multiple monsters all the while seeking to get his revenge against the demon. But close to that place, the demon was doing what she usually did, using her troops of orcs/demons to attack an elves village, killing dozens of people in pretty brutal ways, leaving the place covered with a bunch of blood, all to steal once again a dragon egg. Ordering her minions to kill the rest, the little elf Brief is saved after Panty attacks the minions. Remembering him, the demon taunted Panty before teleporting away with the egg, leaving her minions there to die at the hands of the vengeful Panty.
As Panty, the dragon Stocking and Briefs made their way to the castle of the demon while facing a variety of threats, the demon got to use the egg and envolve herself in its power, transforming once again into a two-headed dragon. Facing against the Warrior and the dragon Stocking, the now Two-Headed Dragon attacked them with everything, showing to really enjoy making them suffer, even getting to see that Stocking was the dragon that came from one of the eggs she lost, but this didn't stop her from killing the dragons while Panty couldn't do anything to stop it. Completely fueled with rage, the Warrior used the corpse to endure the flame attack of the two-headed dragon, using its body to go through one of the heads, before finishing the last one with one last powerful attack. At the end, Panty sits on the corpse of his former enemy, having fulfilled his quest of revenge.
Mitigating Factors
So, let's talk about this. First of all, the Two-Headed Demon lacks any type of redeeming qualities that the original Scanty and Kneesocks have, being a completely sadistic demon who only seeks to become more powerful and cause as much pain as she can just for the hahas, of course not redeeming at any moment or helping the heroes in anyway, while also lacking any interaction that could have show care for each other (and anyways, they are pretty much the same person). Oh and she also doesn't show any concerns for her minions, gladly abandoning them to die with no remorse.
The important thing here is if the demon is comedic, as well, this is still Panty and Stocking... And taking account all of this episode, I will say no, the demon has no comedic moment at all in all of the episode, with the threat that she poses and all of the destruction and deaths that she causes being played incredibly straight for some reason, which is what happens with pretty much all of this episode, which goes into a more dark setting that is meant to be taken seriously in a way. The only thing that could be seen as comedic is that this story has the characters of Panty and Stocking, but the episode never really tries to make this comedic really, they are not even call at any moment for their original counterpart names, so that shouldn't be an issue either.
With all of this into account, the complete change of the setting, the tone being a lot more darker than the original more comedic series, lacking pretty much any type of jokes (with the Two-Headed Demon lacking any) and with her having all of her crimes being played straight, I say the Two-Headed demon is serious enough to count here.
Heinous Standard
Welp, yeah, easily passes the heinous standard. The Two-Headed Demon is the one who sets the heinous standard of this setting, and she easily passes the baseline by destroying and killing everyone in a village (including Panty's relative), to then attack the elves' village killing dozens of people brutally by mutilating their corpses, to then order her minions to kill the rest with no remorse. And of course, we also have how she succesfully killed the dragon Stocking, which adds another thing for personal villany, with the demon being pretty much implied to enjoy attacking villages in the same way, and seeking to continue doing that after obtaining her whole power and killing Panty, so yeah, easilly passes.
Final Verdict
A surprising yes for this serious version of Scanty and Kneesocks.