Can't confirm if it will be the first season or not. Though the one I think will most likely be PE is Valentino.

I don't know much. But maybe as of now, Valentino is the most heinous. Though, remember that HH is in the same canon as HB, so he'll have to compete with villains from that show, too.

Off topic, but where would Crimson from HB stand on the moral scale? The closest I would think of is a low-PE.

@Eleeysium As of now, no to Crimson, his worst actions, while taken much more serious, are not unique to the Hazbin Hotel universe.

I've never seen people say that he's a bog-standard Mafia boss. I remember there was a NPE proposal for him that was undetermined. Ironically, his Journey to the Light counterpart is NPE since that version is even worse, with his only prevention being that his death was comedic.

And what's more ironic? The PFP on my profile is my Rainbow Friends OC that's coincidentally named Crimson. And my Crimson is meant to look like a stereotypical demon while the HB Crimson is an imp. Plus, the naming of my Crimson is coincidental as I didn't base him off of HB or anything else.