WMG / Ruby Gloom

Misery is a banshee.
This is implied in the show, even if it's not official. She a harbinger of disaster, she wails when she tries to sing, and she's doesn't look entirely human. Also, you only ever see her female relatives (It's a well known fact that banshees are always female), and they are all remarkably similar to her. This is bacause banshee genetics are different. Banshees procreate by mating with males of other hominid species - Often humans, but also fairies, elves, or even vampires - but their offspring will always be daughters, and always banshees.
  • That would also explain how she says all the men in her family died from quicksand: she was lying, and they all just died because, well, they were mortals.
  • Can I get a source on this "well known fact"? Because the word banshee comes from "bean sidhe", meaning "fairy woman". They were thought to be some sort of spirit, generally. Vampires are not really huge in Gaelic/Celtic mythology and vampire-like mythology are more along the line of fairy spirits with vampiric qualities, not what we would call vampires today. I've read a lot of books on this and never run into that particular claim. Also, calling something a "fact" when it comes to mythology is a little... amusing.

The show takes place in a post apocalyptic future where only immortal creatures have survived.
It explains the ever cloudy climate and the monster children all living together in a deserted mansion. Perhaps the end was brought about by miseries eternal bad luck.
The inhabitants of the house are all adults.
They're proportioned exactly the same as the other adults on the show, and Misery has cousins who are quite obviously children. Frank and Len have several tattoos. This also solves the question, "How do these 6 kids own this massive plot of land?"

Banshees are immortal.
This is the reason why Misery survives, and quickly heals, from any accident that happens to her. This is also why she acts so calmly even when she thinks something is going to end with a disaster - she knows that she'll survive it. However, she often worries that her friends will get killed; that's why she is sad so often. Further proof: During a family reunion we are introduced to Mayhem, a relative who is old enough to remember the dinosaurs. Granted, that whole family reunion might have been a dream, but prior to that, she speaks of Mayhem as if she was still alive. She speaks the same way of Migraine, a relative who was aboard the Titanic. In another episode, Misery looks exactly the same in a flashback from seven years ago. Furthermore, Misery owns the key to the lost city of Atlantis and it was given to her by her great-great-great grandmother (personally), who got it from her great-great-great-aunt (personally), who won it in the Atlantis bake coven - You do the math.
  • Plus, even if it was a dream, Misery's line about the family reunions only happening once a millenia and that she'll see them at the next one...
  • Except for the fact that Misery is near-constantly mentioning relatives who are implied or even outright stated to be dead...
  • In a mythological sense, this is not out of the realm of possibilities. The sidhe are often said to be either immortal or to live for hundreds to thousands of years.

Misery's family are Identical Grandchildren.
In the "Misery's Family Tree" skit, Misery shows Scaredy Bat slides of her great+X grandmothers. None of them showed up for the reunion, and Misery refers to them in the past tense, implying that they're dead. They're all identical to Misery, save changes in attire.

Instead of being immortals, Misery and her current generation of relatives are instead descendents that look and act like their forebears. Mayhem would be one of the only exceptions; maybe she spent a few million years as a Human Popsicle.

Misery and her family are an alternate universe equivlent to The Endless.
A family of powerful beings with Perky Goth designs that are personifcations of abstract concepts that all start with the same letter. Never Heard That One Before.

The series is set in the same world as either Corpse Bride or the cartoon Beetlejuice—or both!
This would explain why the characters never age, why there's skeletons running around (maybe Skelly-T, Jacques and Bonejangles are related!) and why a bunch of kids own a large amount of land-since they're dead, who says they can't? Heck, maybe Bonejangles or Jacques owns the house and just lets them live there, explaining why Skelly-T pops up so often and takes such an interest in Skullboy! OH MY GOD, IT ALL MAKES SENSE!!!!

...I smell fanfiction...

  • That one time Skullboy has a stereotypical French mustache, he actually looks just like a chibi Jacques.
  • I feel that it's equally possible that the series is set in the same world as "The Nightmare Before Christmas" or "Monster High".

Ruby is a witch and Doom Kitty is her familiar.

Assuming he ever was fleshy, Skull Boy used to be African-American or black british.
He just really seems like an extra-geeky, extra-square black kid character, and in the episode with the N'Awlins themed skeleton music club, he finally manages to pull of being hip and it's in that was that only Joe Cocker, pimps, or both can look even remotely natural when doing while white. This also adds highly interesting (but not necessarily truly unfortunate) Unfortunate Implications to some of the things he thinks his ancestors are/did (such as traveling to and exploring new places without being involved in the actual navigation, or descended from Shakespeare).

It's all in her head
Ruby is a mental hospital patient, and she hallucinates a whole world. The "bright side of the dark side" is not the sweet side of monsters, but rather the happiness experienced during insanity.
  • Because every series needs one of these to make everyone depressed. But in all seriousness, it makes a strange amount of sense when you think about all of the inconsistencies and impossibilities of Gloomsville. Skullboy would be a boy/man she had/has a crush on. Possibly the doctor who treats her. Misery would be a sickly adult who believes herself to be a fictional species. Iris may actually have only one eye, though because of her adventurous nature, brought about by whatever is wrong with her. Frank and Len would be a pair of twins who really do believe they are stuck together. And Scaredy Bat, Poe, and Doom Kitty would be actual pets of hers, or even of the other patients. Now excuse me while I go watch some episodes to get the depression this has left me out of my system. Oh Misery, why you so adorable?
  • How about Poe is the actual doctor?

Ruby's the only survivor of her rich family, and her friends are all boarders.
Her family used to be rich, and lived in the mansion; something happened to everyone but her. Now she's got various undead/supernatural friends to keep her company.

The show will be Un-Cancelled and will return with a third seasonnote 
It will also FINALLY air in the United States(And not just on Netflix). Which channel the show will broadcast on is open to speculation.

The house is a summer camp for rich monsters.
The technology in the house is "behind" on purpose; the characters are doing their own chores the old-fashioned way to learn responsibility and life skills. It explains why they never really want for anything and are supposedly small children left by themselves with nothing to do but play and keep the house clean.
  • Frank and Len just sort of wound up sleeping in the shed so they wouldn't keep the house up at night with rock and roll.
  • Considering the ravens have their own treehouse, they are probably permanent residents.

Skull boy is relative of Baron Samedi
Why not ?

Misery was lying about the lead in her blood
It would help explain why she is sick so often but it's not particularly conductive so it wouldn't explain why she's a living lightning rod. At that time she was trying to hide that she was actually one of The Fair Folk and iron (which is conductive and magnetic) is as toxic to her as lead is to humans.
  • Might be supported somewhat. In an episode in either season 2 or season 3, Misery comments that she and her family have a high amount of iron in their blood.

The reason Skullboy can't find his family is that his dad is Grim.
At first glance it seems like he can't find his family because he's dead, but there are a variety of dead people around and they seem to be fine. Maybe thanks to Billy and Mandy's eternal slavery contract with Grim, he can't call back to tell his kid what's up. So there's another WMG: Skullboy is a teenage reaper.

The characters are at camp.
The house is a small sleep-away camp for undead kids where they learn life skills like doing their own laundry and cooking. The camp doesn't quite have enough money to get new appliances, hence the wringer washing machine and phonographs alongside amps and ear buds.

Skullboy ate the Revive-Revive Fruit.
Because he is not sustained by muscles or organs, it's... HIS SOOOOOUUULL!!!

Misery does not have to be asleep to sing.
We see her sing without screeching when she's on a melting ice floe, as well as in the musical numbers. She just needs to be unaware of the fact that she's singing.

Skullboy really is related to Misery's family
It just seems to reek of a Chekhov's Gun that there's no surviving men in Misery's family and Skullboy can't seem to find his family. It may be that Skullboy and one of Misery's ancestors were the forerunners to her bloodline.

Misery needs Ruby and the others
Just look at how she breaks down crying when she thought Ruby was moving away and she's by far the gloomiest character on the show in general and always looks sad, so it's not much a stretch to think that she needs them to keep her emotionally stable. If they suddenly all left her all alone, she might... well...

It's a sleepaway camp.
The characters don't live there the whole year round, and part of their camp responsibilities is taking care of themselves and the house they live in. Being mostly unsupervised and very unstructured is part of the appeal.