#ruby gloom headcanons

[nastyboker]

My friend has redrawn a part of this old art of mine and I realized that I never posted it here.

Back in the old days when I was hyperfocused on Ruby Gloom I wrote down all mentions of Misery's relatives and created a family tree that would fit them all. Then I decided to draw some of them. It was an answer for some Rus Ruby Gloom Ask where I was answering for Misery. The question was about male family members so I shared my headcanons.

The musketeer great great great grandfather was mentioned but never shown in the series so I designed him myself. He was the 4th musketeer no one cared about.

The guy on the left appeared once but him being a part of the family is purely my headcanon (he died bc of the black plague).

As well as character Ween on the bottom — I think he has a clear resembelance to Meek who could be his son. Great grandmother Misery and Ween were some of the founders of Gloomsville and shared the same grave in its cemetery.

The vampire guy is a result of my theory that Misery is related to vampires. The theory explains that her 8 times great granduncle fell off a ladder in 1961. His wife Maelstrom was mentiond in the series but was also designed by me. This family line mostly men, died in a quicksand, probably, in the same place where Gloomsville was found later.

[box-of-chaooos]

Updated anatomy and heacannons list of frank and len 🤘🏻

Anatomy

Their nervous system is conjoined. Whilst they have their respective sides each will still feel pain if it’s from the others respective side like in sunny daze (days?) len steps onto the hot steps and frank feels it too. Only both feel it if it’s a strong pain, if len bumped his leg or something frank wouldn’t feel that only len and vice Versa hence why they can pinch each other and the other not feel it.

They have 2 stomachs but sometimes still eat for 1 person. Ruby might make a batch of special cupcakes so they’ll halve it between them, but if it’s a normal meal or there’s enough for everyone to have their fill the two will eat as they wish as well, Ruby usually provides more for them both.

Both are technically zombies, as mentioned imo frank died of suffocation and len of Illness so both of them are quite slow, len more so because his brain was shut down so quickly as a baby due to his illness hence why he blinks out of unison a lot or seems to stare out into space alot. Frank also blinks out of unison or can be ditzy but slightly less so.

Headcannons

Frank is nonbinary and bisexual, he doesn’t have a preference

He has one blue (right) eye and one green (left) the blue is more prominently coloured than the green which is a sort of muddy green as opposed to his bright blue eye.

They’re autistic and have a strict routine they follow each day but it’s usually messy due to len (why in lens area)

Do not call him frankie he will actually strangle you.

Whilst he loves rock he typically likes sorts of 80s rock or alternative and they quite likes jazz too.

He has a fear of suffocation due to the way he died as a kid, he constantly has anxiety about how he might stop breathing randomly or even end up drowning.

He is actually more adventurous than len, he loves to get outside (mostly in hopes of finding a talent scout)

Between the two they take the career a little more seriously than len

Assigned female at birth

They’re technically older than len having been born first

———————————————————————

Len is trans and gay but he always talks about girls he just appreciates a beautiful or hot lady when he sees one

He’s gay but put a muscular punkish lady infront of him he will say some shit that is straight as.

Autistic and adhd, he struggles to stick with routine and constantly wants to do his own thing which is tricky due to franks routine.

He tattooed himself with a pen and safety pin because he was bored.

To him the music career isn’t as serious and more fun

The better singer of the two (don’t tell Frank)

He has one green eye (right) and one blue (left) his green eye is a very bright green whilst the blue is more greyish which is the opposite to franks

He is a raging insomniac and barely sleeps which ends in him falling asleep through the day all the time randomly.

Loves all rock categories but favours heavy metal and punk rock even death metal, though he loves hairspray/glam metal too.

Assigned female at birth, but doesn’t mind embracing his feminine side E.g wearing eyeliner

The pink parts of his eyes aren’t makeup rather from when he died his skin drooping what you see is his water line.

Has a very server phobia of illness and sick (emetophobia) due to his death as a kid and often avoids eating due to it, checks dates constantly misery helps ease the worries.

[zothousand]

Twilight Town Skull (Boy) voice headcanon

@cosmiischillin

Miiiiight make more of these in the future (already got one for Ruby, Iris, & technically Misery as well, but idk)

[violetjosh]

no fucking joke my headcanon voice for shion has always been misery from ruby gloom

[irradiatedpathogen]

voice claims

Cane - McCafferty

Irah - Stacy (phineas & ferb)

Dola - Misery (ruby gloom)

I hope this actually gets made in the future lol, if not i still hope people fw my ocs 8ecaus i might start making more content with them ::::3

[macbxth-pdf]

Skull Boy and Ruby Gloom are butch\femme coded but yall not ready for that.

[b0yfraudz]

Girls I headcanon as Lesbian PT5

Toralei Stripe-Monster High

Icy-Winx Club

Darcy-Winx Club

Stormy-Winx Club

Brittany And Whittany Biskit-Littlest Pet Shop

Blackfire-Teen Titans

The Dazzlings(Aria Blaze ,Adagio,Sonata Dusk)-MLP

Strawberry Shortcake & Orange Blossom-SS

Ruby Gloom-Ruby Gloom

Emira Blight-The Owl House

[skippudippu]

HELLO RUBY GLOOM NATION

I decided I’m gonna share my headcanons via ao3 :DD feel free to check it out !!

[andtheywere-gloommates]

skullboy is a ska enjoyer ‼️‼️

[kakusu-shipping]

Agere List

To me Carer/Regressor dynamics are different than your typical Romantic/Platonic/Familial type of realationships, so I've decided to make a separate list for F/Os who are my Caregivers, or who I Caregive for.

This is very different from a headcanon list of characters who I think are Caregivers/Regressors, this is characters I personally have this relationship with. I am also only a Caregiver in a Fictional space, and cannot CG a real regressor in the real world.

Thankyou for your attention, list below the cut.

Caregivers

Alder - Pokemon BW - Grandpa

Darmanitan - Pokemon BW - Babysitter

Whimsicott - Pokemon BW - Babysitter

Maractus - Pokemon BW - Big Sister

Molayne - Pokemon SuMo - Big Brother

Hassel - Pokemon SV - Daddy

Salvatore - Pokemon SV - Trainer

Stoutland - Pokemon BW2 - Companion

Chesnaught - Pokemon XY - Knight

Bloodmoon Ursaluna - Pokemon Scarlet/Violet - Mommy/Yandere

Beware - Pokemon Anime - Mommy

Doctor Mario - Super Mario Series - Doctor/Yandere

Craig Cuttlefish + Octavio - Splatoon - Grandpas

Callie + Marie - Splatoon - Big Sisters

Agent 7 (Eight) - Splatoon OC - Babysitter

C.Q. Cumber - Splatoon 2 - Boss/Yandere

Mr. Grizz - Splatoon 3 - Boss/Papa

Papyrus - Undertale - Babysitter

Chara - Undertale - Chaotic/Babysitter

Swatchlings - Deltarune - Butlers

Gaster - Deltarune - Father/Eldritch

Enderman - Minecraft - Companion

Winston - Overwatch - Teacher

Moira O'Deorain - Overwatch - Doctor/Babysitter

Siebren de Kuiper (Sigma) - Overwatch - Grandpa

Sombra - Overwatch - Big Sister

Maugaloa Malosi - Overwatch - Chaotic/Big Brother

Teruteru Hanamura - Danganronpa 2 - Babysitter

Genocide Syo/Jack/Jill - Danganronpa UDG - Chaotic/Yandere

Shirokuma - Danganronpa UDG - Daddy/Yandere

Toy Freddy - Five Nights at Freddy's - Big Brother

Nightmare Fredbear - Five nights at Freddy's - Guardian

Huggy Wuggy - Poppy Playtime - Babysitter

Mommy Long Legs - Poppy Playtime - Mommy

Wally Darling - Welcome Home - Yandere/Neighbor

The Doctor - Little Nightmares - Doctor

Morgo - Little Misfortune - Eldritch/Yandere

Anna (The Huntress) - Dead by Daylight - Mommy/Yandere

Chzo - Chzo Mythos - Eldritch/Father

Kyle + Brett - Drive Time Radio - Chaotic/Eldritch

The Narrator - Stanley Parable - Eldritch/Guardian

Micheal Bleak - Wayward Children - Guardian (former)

Jill Wolcott - Wayward Children - Guardian

Aziraphale - Good Omens - Guardian/Knight

Crowley - Good Omens - Chaotic/Guardian

Edgar + Alan + Poe - Ruby Gloom - Babysitters

Scardy Bat - Ruby Gloom - Big Brother

Beetlejuice - Beetlejuice the Animated Series - Chaotic/Papa

Mashirao Ojiro - My Hero Academia - Babysitter

Mei Hatsume - My Hero Academia - Chaotic/Big Sister

Pantherlily - Fairy Tail - Knight/Papa

Shiro Ashiya (Aciel) - The Devil is a Part-Timer - Stern/Papa

Watanuki + Domeki - xxxHolic - Daddies

Chieko - Princess Jellyfish - Mother

Mayaya - Princess Jellyfish - Chaotic/Big Sister

Muta - The Cat Returns - Companion

Baron Humbert Gon Gikkingen - The Cat Returns - Royal/Babysitter

The Beldam - Coraline - Yandere/Mother

Anger - Inside Out - Protective/Dada

Sadness - Inside Out - Mama

The Storyteller - OC - Eldritch/Guardian

Regressors

Cyrus - Pokemon Platinum - Permaregressed

Arven - Pokemon SV - Kid

Giacomo - Pokemon SV - Involuntary/Toddler

Saguaro - Pokemon SV - Dreamer/Baby

Hydreigon - Pokemon BW2 - Trauma/New Born/Baby

Smeargle - Monster Mind - Dreamer/Puppy

Princess Peach - Super Mario Series - Baby/Princess

Genji Shimada - Overwatch - Dreamer/Kid

Mako Rutledge (Roadhog) - Overwatch - Trauma/Baby

Toko Fukawa - Danganronpa 1 - Involuntary/Baby

Celestia Ludenburg - Danganronpa 1 - Dreamer/Gothic/Kid

Kyle Klim (K) - Virtue's Last Reward - Kid

Kazuaki Nanaki - Hatoful Boyfriend - Dreamer/Baby

Hitori Uzune - Hatoful Boyfriend - Trauma/Involuntary/Toddler

The Little King - Hatoful Boyfriend - Baby/Toddler/Prince

P03 - Inscryption - Involuntary/Bratty/Baby

Lapis Lazuli - Steven Universe - Trauma/Ageless

Nezu - My Hero Academia - Trauma/Involuntary

Tomura Shigiraki - My Hero Academia - Newborn/Baby

Dabi - My Hero Academia - Involuntary/Bratty/Kid

Himiko Toga - My Hero Academia - Dreamer/Toddler

Jin Bubaigawa (Twice) - My Hero Academia - Trauma/Toddler/Kid

Erza Scarlet - Fairy Tail - Involuntary/Big Sister

Juvia Lockser - Fairy Tail - Permaregressed/Toddler/Kid

Gajeel Redfox - Fairy Tail - Involuntary/Big Brother

Toma E. Fiore - Fairy Tail - Involuntary/Prince

Tamaki Souh - Ouran Highschool Host Club - Involuntary/Prince

Takashi Morinozuka - Ouran Highschool Host Club - Baby

Makoto Katai - Komi Can't Communicate - Baby

Embarrassment - Inside Out - Baby/Toddler

Micheal Myers - Halloween - Permaregressed/Evil/Kid

Jason Voorhees - Friday the 13th - Trauma/Baby

Brahms Heelshire - The Boy - Permaregressed/Toddler/Kid

Beetlejuice - Beetlejuice the Musical - Spooky/Horror/Baby

Playmates

N - Pokemon BW - Permaregressed/Baby/Toddler

Jacq - Pokemon SV - Dreamer/Big Brother

Miriam - Pokemon SV - Dreamer/Nurse

Kieran - Pokemon SV - Evil/Pokemon

Gooigi - Super Mario Series - Big Sister

Kirby - Kirby series - Toddler/Big Brother

Flowey - Undertale - Trauma/Big Brother

Vulkin - Undertale - Pet

Ralsei - Deltarune - Prince/Big Brother

Viktor Humphries - Slime Rancher - Kid

Pheonix Wright - Ace Attorney - Involuntary/Teen

Monokuma - Danganronpa - Dreamer/Object

Kazuichi Soda - Danganronpa 2 - Involuntary/Toddler

Moon - FNaF Help Wanted 2 - Baby/Toddler (former)

Kissy Missy - Poppy Playtime - Trauma/Kid

Boxy Boo - Poppy Playtime - Permaregressed/Object

CatNap - Poppy Playtime - Trauma/Cat

Grendan Highforge - Drawtectives - Dreamer/Old Dog

Rosé - Drawtectives - Pre-Teen

York - Drawtectives - Dreamer/Little Brother

Muriel - Good Omens - New Born/Ageless

Frank + Len - Ruby Gloom - Teen/Toddler

Katsuki Bakugo - My Hero Academia - Toddler/Little Brother

Banba - Princess Jellyfish - Hyperfixation/Kid

Joy - Inside Out - Bratty/Big Sister/Kid

Fear - Inside Out - Protective/Big Brother

[pumpkinsy0]

Do u have headcanons about or what do you think about a 90s or 00s AU (maybe) where Curly Shepard is a punk and Ponyboy a goth or a babybat? ^_^ Like imagine purly but ponyboy tries to show his obsession for edgar allan poe and curly or the gang JUST DON'T GET IT 😭

wym anon that literally already IS purly🙄🙄

BUT YEA I DO HAVE HCS!!!! o(^-^)o

(for context who dont know, baby at is the name for like ppl who r newly goth basically, theyre just starting out listening to music n stuff like that)

•since curly is punk here and the whole idea of punks is essentially anti establishment and love individuality i will NOT make him make fun of pony for being goth, especially when hes a babybat hes just embracing himself

•also curly is curly i feel like hes a bit morbid himself and would be at the very least interested in edgar allen poe, so even if he wasnt punk he wouldnt make fun of pony for liking him, even if he does thats just bc hes being friendly and just does NOT like poetry

•ill place this in like, late 90s and early 2000s, so there is that huge thing against goths and punks for being ‘weird’ and against god or something along those lines

•curlys pretty used to being targeted for being different for his punk style and such while pony isnt exactly used to that so i imagine that hes more protective while ponys trying to figure himself out in that regard

•some bands pony would b interested in is evanescence, the cure, and siouxsie and the banshees, london after midnight, of course there IS more but these r like more so his favs

•how pony found out about gothic bands was like, a song was playing in darrys car radio and darry didnt rlly like it so he changed it but the song was already stuck in ponys head

•he brought it up to curly but pony was just like ‘idk maybe itll pass’, it in fact DID not pass and later they was just chillin in curlys car and the song came back on the radio and pony was like ‘neuron activated’

•curly was personally not rlly into the song, but hey, ponys happy so its whatever

•personally i imagine that pony doesnt have a gothic STYLE more so he has a love for gothic songs and literature, yknow what i mean??? but maybe he does borrow some clothes from curly thats more on the gothic side or thrifts some clothes

•other than edgar allen poe, he does like phantom of the opera, frankenstein, dracula, carmilla, dr jekyll and mr hyde, also he would like ruby gloom (thank my gf for this hc)

•his art style is kinda influenced by those media actually

•as for what type of goth he is i could mostly see him being like a geek goth, but he is interested in the looks of victorian goths and gothabilly goths

IVE BEEN TALKING ABOUT PONY FOR TOO LONG NOW ON ABOUT CURLY

•tbh, not much to add for this guy, punk curly is literally just regular curly but more understanding of who he is and what he wants in the world yknow??

•think of curly but actually a lil more, idk thought provoking in his own curly way with a better understanding of the world

•MAY I INSERT MY HC OF CURLY HAVIN AN AFRO MOHAWK HERE🗣️🗣️

•he is from a haitian household tho and haitian moms especially tend to be more, religious and all that jazz, so while tim and angela get their ears yelled off for well being them, its especially happening to curly bc in his moms eyes hes “turning away from god” n what not being a “vagabon” as many haitian moms would put it

•he likes customizing his own clothes, he thrifts and gets a bunch of hand me downs so might as well make them look cooler

•hes a graffiti artist and hes acc pretty well known, everyone knows its him but they dont rlly say anything cause 1) hes curly shepard but 2) his work rlly isnt that bad actually

•i could totally see him liking green day and he does NOT like fall out boy but he does like a coulle of songs from them (much to his dismay

•hes picking up guitar (how he afforded it??? i payed for it lets just say that)

WHEN IT COMES TO THE GANG, they dont rlly get pony being goth, they support him of course, but they do tend to make fun of him a bit</33 but darry, soda, and johnny do try to understand him more, its rlly just two

ps anon my gf said she loves u for ur idea (shes goth, u got the goth stamp of approval)

[reedipop]

character headcanons because im eatign a sandwich

hajime hinata

transmasc he/him

bi

took him a long time to realize he liked nagito back because he used to have a crush on chiaki

5' 7"

likes watching stupid reality shows with nagito

not really a headcanon but i draw him with slightly darker skin than canon

nikei yomiuri

transmasc he/they

5' 3"

demisexual

coffee/energy drink addiction

likes oatmeal raisin cookies

rei mekaru

transfem

married to teruya

secretly really likes physical affection

5' 11"

emma magorobi

straight ally

she/her

dating hajime (makunouchi) and calls him darling

absolutely loves ruby gloom

5' 6"

hajime makunouchi

he/him

bi with female preference

dating emma and calls her babe

really likes holding emma bc she's tiny compared to him

6' 3.5"

nagito komaeda

amab he/they/she

gay

had a huge crush on hajime for a while and was ecstatic when his feelings got reciprocated

cries when he gets yelled at

doesn't like sweets very much

really skinny

6' 0"

chiaki nanami

she/her/mew

has full 100%s in my friend peppa pig and paw patrol mighty pups save adventure bay and she's working on spongebob battle for bikini bottom

has xbox game pass ultimate

aroace

qpr with sonia

[comforttears]

Can we get a one shot or hcs of lil Pest? U can choose which one but if u do the one shot could we get CG Poob or Infected pls? :3 -🐾

— Little! Pest headcanons—

🍼 Spooky Regressor Pest (Little age: 2-4)

🪲 — He's a secret little, Pest is discreet with his agere, he doesn't want anyone to find out.

🧷 — Pest enjoys carrying something in his mouth, whether it's his paci or his teether, but he usually carries his paci.

🪲 — Apples! Apples and apples! He loves apple juice, caramel apples, applesauce, but especially homemade apple pie. It's obviously his comfort food!

🧷 — Pest has a comfort with Sam (character from the movie Trick 'r Treat); he has a plushie of this, which he sometimes carries with him.

🪲 — Another comfort plushie is Mr. Paws! His centipede that he always carries with him at bedtime!

🧷 — He has a collection of porcelain dolls and Monster High dolls!

🪲 — Pest turned his bed into a pillow fort, to simulate an underground burrow.

🧷 — He sleeps wrapped in a sheet, as if he were a pupa again, although he is a bug-rrito.

🪲 — Enjoy watching cartoons like Ruby Gloom, Creepie, School for little vampires, his favorite is Beetlejuice!

🧷 — Although he doesn't say it, sometimes he would like Infected and Poob to take him trick-or-treating, he's very proud...

🪲 — Pest throws tantrums if he doesn't sleep well or the apples have a sandy texture. Sometimes he hits when he feels upset with something.

🧷 — The beetle usually repeats the phrases of his favorite characters a lot.

🪲 — Enjoy fruit snacks a lot! Also natural juice, so there will be no problem giving healthy snacks.

🧷 — Pest if he was in Little Space along with Infected and Poob, he would scare them with ghost stories.

🪲 — He likes to bake, he always serves his meals in a way that entertains him and whets his appetite.

🧷 — "How long until Halloween? Can I put on my costume now? Can I be a vampire now?"

🪲 — Pest likes to collect things and count them and sort them by size and color.

🧷 — Secretly he is usually little with Prototype, the robot is so sweet that he cares and plays with him

I made a oneshot, you can also suggest your ideas and I'll try to write them down! Anything you need you can tell me! 🧸ʕ⁠·⁠ᴥ⁠·⁠ʔ

Requests are open!

[zothousand]

Twilight Town Ruby & Halo voice heacanons

@cosmiischillin

These are probably my favorite (non Mario/Star Spirit Saga) voice headcanons for characters, Halo's especially for some reason

[cosmiischillin]

I am alittle bored so hey! Here are some Fun Facts/Headcanons for the characters in Twilight Town (Reminder: Twilight Town is takes place in a rebooted version of the Ruby Gloom cartoon where they’re all adults)

1. Iris is the youngest of the main 8 with Ruby being a few months older. Frank is considered the oldest being a second older than his twin Len. (Halo would have been oldest overall at 2100 but I decided to only portray her as 21)

2. Misery is a native Irish speaker though she can speak several other languages thanks to her family tree including Latin, Chinese, French, and Swedish.

3. When Skull was 13, he tried to change his name to Skull Guy but literally no one liked it so he dropped the second part of his name. Misery, Frank, and Len still call him Skull Boy from time to time to tease him since they’re older than him.

4. Ruby’s middle name is Lily which I got from Lily Munster.

5. Frank is actually Frank II. His father, Frank Frankenstein is the first. In fact. My friend said the twins names together sounded like Frankenstein (Frank) L(eN) Stein.

6. Both Frank and Len have separation anxiety due to how long they’ve been conjoined. If not near by each other for long periods of time, they get anxious and tend to lash out more.

7. Jackie was my first ever OC for anything and back then her name was Lantern. She was never gonna be shipped with anyone until recently where she’s with Len.

8. Misery has the highest kill count of the group at 666 via natural disasters and freak accidents. Frank and Len are in second place with 25 kills and will resort to eating humans to get rid of evidence.

9. Skull has never killed someone but he is capable of it as he took up marksmanship as one of his 100+ hobbies.

10. Ruby’s more monstrous side is based on Other Mother from Coraline, Nightmarionne from FNAF, Eltrich and Lovecraftian monsters, Raggedy Ann, and Wally Darling from Welcome Home!

[th3-circus-coll3ctiv3]

May I request Regressor!Crymini (Hazbin Hotel) headcanons?

I hope you like these!

🍒💀🍓 Regressor! Crymini Headcanons🍓💀🍒

She regresses from 4-8 involuntarily due to trauma and to deal with anger! On occasion, she does slip younger, about 2, though that is usually after not regressing for a long time.

She's very fussy and will throw tantrums if she feels like she isn't being heard.

Her caregiver is Husk! She usually hangs around the bar when she's little, and he always has juice or milkshakes ready to go!

Her favorite shows to watch are Ruby Gloom, Lilo & Stitch, and Yo Gabba Gabba!

She has a lovey security blanket that looks similar to Husk, as well as a few Plushie Dreadfuls!

Her room has a corner that acts almost as a nest, with bookshelves filled with picture books, stuffed animals, blankets, and tons of pillows!

Her favorite color still is red, though she seems to embrace pinks and yellows a bit more when little! Black is also still prevalent, but she would much prefer a dark maroon than pure black.

She easily gets overstimulated when regressed but has a difficult time expressing it. Luckily, Husk knows his little very well and understands her feelings. He also made her a feelings chart show she can identify her emotions better!

Music!! She's always humming or making up songs, playing with kiddy guitars or keyboards, asking others to sing... It means a lot to her!