Thanks for making this Wraith, fun way to have some interesting conversation about the event
To start with, I unfortunately have not been visiting since "The Icon Years", so I've only seen Jack and Chance in power, but I have read up and seen a bunch of videos so I THINK I can speak pretty well on Icons and the important lore characters.
Here's my list of lore characters:
10. Director - He's a psycho director, basic story and pretty basic design but I like that concept. Helps that I'm a film nerd.
9. Chance - Funny that in HER year, she was so boring and pointless, but when she's the sidekick she absolutely shines. She's funny and yeah she's a hot psycho clown whatever.
8. Cindy - Creepy killer kids are always a fun trope. They wrote some insane conceptual stories for the years she was supposed to be the icon, and MAN they would be insane to see played out.
7. Nathaniel Crowe - Very cool story, some of the most in-depth lore available for the event. I. Just. Wish. He Actually. Existed. If I see him in action I'm sure he'll shot the Hell up on the ranking.
6. Usher - Yeah, he's preeeeetty lame and doesn't have too interesting of a story, but I love what I saw from his house and I had a very funny interaction with him at scareactor dining in 25, made me love the guy!
5. Sam Meetz - I want to see a Meetz Meats house in person so, so bad. (Hopefully the year 30 anniversary house, please please) From all the videos I've seen of Leave It To The Cleaver it looks like such a fun, interesting dark comedy house. The little article Universal released about him recently made me enjoy him that much more. Keep the streets clear of riff-raff, Meetz!
4. Terra Queen - She has a super interesting story and really well built lore. I love how much stuff tied into her story her year, and I wish I could have seen her in person. Maybe HHN30?
3. Slaughter Sinema Announcer Guy - Not even a joke, he's technically a lore character since he exists as the trailer guy at the Carey Drive-In. His voice made me so happy, god I loved that house.
2. Jack - I mean, yeah, it's Jack. What else can I say?
1. H.R. Bloodengutz - Funny, brutal, genuinely kinda scary. Killer-looking house and so much potential for a greater expanded story and more fun houses with new concepts. Would love to see him hold down his own event one day, if his actor is still available.
Honorable Mentions! Bloody Mary, The Caretaker, Eddie, the Warden guy from Hellgate Prison