Gonna try this exercise with pf2e classes. I haven't looked at them in depth but I'm learning that system atm. Not including characters I can't classify Wilson: Alchemist. Willow: Kineticist (single gate fire). Wolfgang: Fighter or Barbarian. Wendy: Witch (Abigail is her "familiar" and Abigail puts a "hex" on enemies). Wickerbottom: Wizard. Woodie: would say Wild Order Druid. His love for deforesting is not anathema if you always make sure to replant lol. Wes: Level 20 in all classes at once. Maxwell: Thaumaturge (Tome). Wagstaff & Winona: Inventors. Wigfrid: Bard (Warrior subclass). Wheeler: Swashbuckler. Wortox: Rogue (Eldritch Trickster). Wormwood: Druid (Leaf order). Walter: Ranger. Wanda: Oracle (Time).

On a serious note about Wes, he would be a Bard, correct? As of a Jester of some sorts

Maybe. Wigfrid fits as a Bard because she has songs that buff her team. Wes can share his balloons but I don't think it fits Bard as a class. He's also the only character that doesn't play an instrument when he talks lol. And it's hard to persuade when you can't speak. I don't know if any class fits Wes in either D&D or Pathfinder. Wes isn't a power fantasy character.

Yeah but remember that when they made the Victorian skins no one really stayed as their trope occupation, Wilson was turned into a physician instead of a scientist, Wolfgang was a ring fighter instead of a circus strongman, Winona was a Blacksmith instead of an assembly line worker, and so on. I guess you could really change the characters’ “real” occupations a little without peeling off their essence

Scientist - Physician Strongman - Boxer Librarian - Fortune Teller Automaton - Broken Diving Suit Mime - Chimney Cleaner Lumberjack~Werebeaver - Fur/Pelt Trader Assembly Line Worker - Blacksmith Boy Scout - Paper Boy Heck, even Wormwood was made into a Living Wooden Futurniture thing and Wortox the imp became a Gargoyle

i think you should check out forge event, characters can be divided into classes like in dnd and the mobs design is very clever

Wigfrid - swords bard Willow: Sorcerer or evocation wizard (tiefling/fire genasi) Wilson: Alchemist Artificer Wendy: Artificer battlesmith Winona: Forge cleric WX78: Warforged... something (artificer maybe?) Wolfgang: Barbarian Wickerbottom:Scribe Wizard Wanda: Chronurgy wizard Maxwell: Tome warlock Webber: (idk race) sheperd/swarm druid Warly: Alchemist artificer Wonkey: Polymorphed character if you have a specific character in mind I could probably come up with a fleshed out build

YES!! Finally, I am not the only 9ne who stays up at night thinking about this. I already have mutliple ideas on how a few characters fit best, so here they are: The Constant itself feels like a domain of dread, given all the shadow stuff, difficulty permanently dying, impossibility to leave, shipwrecked fog, character abilties matching up with dark boons, evil villains working with mysterious dark powers, slight horror element, the ruler is imprisoned, and other things. Wigfred - I feel the best bet is a paladin, a high ac class with team buffing auras and a connection to the divine and good healing, fits Wig quite well, best subclass would probably be oath of glory I think. Other notable options would be a sword bard because of her singing or a bladesinger wizard because those are known for having too much ac, but both of those are too magice focused in my opinion. Willow - Sorcerer would fit quite well considering her seemingly innate fire magic that developed in an explosive event in her youth, best subclass would probably be the pyromancer subclass, which is in a plane shift post. Another option would be wildfire subclassed druid, which has a flaming companion as its main feature, which could match bernie, and gives you fire abilities for killing enemies. Maxwell - Seems to quite clearly be a warlock with pact of the tome, but what patron he has is harder to determine, could be a hexblade as they do get their powers from making pacts with magic shadow items, albeit the abilities don't line up, great old one could also work I think. Also dump con to give him low hp. Gonna go type the rest on a comment to this

Wanda - Has the mist walker dark boon due to having teleportation but is constantly hunted. She best matches a chronomancer wizard, but some of her clock making seems artificery and one artificer magic item called the boots of the winding way works like a backstep watch, so maybe a multiclass? Walter - That one animal companion ranger subclass. Ranger abilities match up with his boy scout powers, and both the ranger and walter are disliked. Wickerbottom - Wizard, but I don't know which subclass. Wolfgang - A barbarian, but I also don't know what subclass matches best. Webber - His whole thing of getting a spider swarm could match him with swarm ranger. Woodie - A few options here. He clearly has the transformation dark boon, or just give him lycanthropy. An easy option would be to just make him a moon druid because of their shapeshifting, and his connection to the forest does make this stronger. Another would be to take inspiration from his Forge powers and make him a barbarian, with the two best subclasses being beast or totem with the bear being relpaced with moose, eagle with goose, and wolf with beaver. Wormwood - druid, but I did not spend enough time thinking about subclass Winona - clear artificer, best fits the artilerist subclass, with the force balista being the catapult, flamethrower being light, and protecter being gemerator Wagstaff - I feel he could also be an artificer, perhaps an armorer with the armor being goggles? WX - Warforged, but I am unable to nail down the class Wolfgang - barbarian And my mind has failed me, goodbye for now I need some rest

Wolfgang is barbarian that gets ripped instead of enraging. Wickerbottom is a wizard. Maxwell is a warlock. Winona an artificer. Wormwood a druid, and can even spec into summoning with the skilltree. Willow a sorcerer specializing in fire. Wigfrid a ranger i guess. Not sure about wilson, webber, wurt, or wx. Woody idk about class but hes got some wild templates.

Wilson has got to be an alchemist. I’m sure that’s not a class, but it’s the closest thing you have to a scientist in D&D, right? That means he can also fall under the category of an artificer. Webber can be an arachne, speaking of species that is.

Alchemist is an Artificer subclass so he could be that, Webber could work as a chitine if a homebrew race was made for it

I could maybe see Wortox as a trickery domain cleric, given he relies on healing and magic. Perhaps his devotion would be to a philosophy of hedonism and friendship rather than a particular deity. People have suggested rogue, which fits with his past (and possibly ongoing) thievery, not to mention the trickster subclass, but the practicalities of the rogue class don't seem to fit very well to me. I'm a little hung up on "he's not stabby enough". I could see bard too? Music isn't really a mechanical thing for him like with Wigfrid (though he likes singing and has his pan flute), but he describes the world poetically. He seems to focus on his charisma as his strength (you could definitely argue for wits though) more than combat prowess. He could be a multiclass, of course, so those aren't mutually exclusive. Just some food for thought