#sir pentine

[heavenboundhotel]

✨SIR PENTINE✨

Name: Elias Pendleton

Species/Origin: Sinner, Snake Demon

Gender/Pronouns: Male - later questioning, He/Him (?)

Sexuality: Unlabeled (Later pansexual, he just doesn't know the actual term)

Year of Birth: 1847

Year of Death: 1888

Appearance:

Personality:

Eccentric, theatrical, and hopelessly unlucky, Sir Pentine is the very picture of a wannabe villain whose bark is far worse than his bite. A snake demon with grandiose dreams of becoming an overlord, Pentine styles himself as an evil genius with cutting-edge inventions, devastating wit, and a fearsome presence—none of which he actually possesses. His mechanical arms, crafted to project power and menace, are prone to spectacular malfunctions, undermining his carefully curated image at every turn.

Despite his villainous posturing, Sir Pentine is deeply anxious, self-conscious, and avoidant in personal matters. His attempts at wordplay and intimidation are laughable, and he crumbles under confrontation, more likely to stammer out apologies than follow through on threats. He desperately wants recognition and respect, believing that climbing Hell’s power ladder will validate his existence and silence his nagging insecurities.

However, Pentine’s soft-hearted nature and inability to truly harm others keep him from succeeding in Hell’s ruthless hierarchy. He overestimates his abilities, underestimates others, and stumbles through schemes with sheer dumb luck as his saving grace. Though he externalizes his insecurities by playing the role of “evil incarnate,” deep down, he’s more kindhearted and moral than he’d like to admit.

Pentine’s over-the-top antics and comedic failures make him a laughingstock in Hell, though he remains oblivious to how little others take him seriously. Still, his persistence—and occasional flashes of ingenuity—suggest that beneath the bluster and insecurities, there might be more to Sir Pentine than meets the eye. Whether he’ll ever realize that himself is another matter entirely.

Backstory:

Born in 1847 in Victorian England, Elias Pendleton came into the world frail and sickly, confined by illness to the indoors for much of his childhood. While other children ran and played, Elias buried himself in books, immersing himself in tales of scientific marvels, alchemical miracles, and fantastical inventions. These stories sparked an imagination unbound by practicality. He dreamed of building machines that could change the world, though he never quite grasped the line between fantasy and reality.

Elias’s parents, well-meaning but strict, unintentionally planted the seeds of his lifelong insecurities. They viewed his fragility as a flaw and his eccentricities as embarrassing, chastising him for his "silliness" whenever he tried to share his lofty ideas. Feeling inherently “bad” or “broken,” Elias internalized their disapproval and began using his tinkering as a way to prove his worth—not only to them but to himself.

As he grew older, Elias’s ambitions outpaced his abilities. He constructed bizarre contraptions that rarely, if ever, worked. Undeterred, he turned to another booming industry of the era: snake oil sales. Drawn in by promises of wealth and recognition, Elias began selling miracle “elixirs” alongside his increasingly impractical inventions. Though his intentions were never malicious, most of his creations were utterly useless, and some caused genuine harm. When customers fell ill or claimed injury, Elias was wracked with guilt but lacked the courage to admit his failures.

Word of his mishaps spread, forcing Elias to flee town after town. Isolated and ashamed, he became a recluse, holed up in small, dingy apartments, where he continued to tinker and dream of success. Despite countless setbacks, he clung to the hope that his next invention would finally redeem him. But Elias never found the breakthrough he sought.

In 1888, at the age of 41, Elias met his untimely end in a freak accident of his own making—an experimental boiler he’d been testing exploded, taking him with it. His death was as chaotic and absurd as his life, and he awoke in Hell with a newfound sense of purpose. Surely, he thought, if he was condemned here, it must mean he truly was a terrible person all along.

Eager to embrace his “true nature,” in order to push away the deep pit of self-loathing thar came with it, Elias transformed himself into “Sir Pentine,” a self-styled evil genius. He crafted a pair of massive mechanical arms—compensating for his lack of limbs in his demonic form—and filled his lair with egg-shaped robotic henchmen of dubious utility. Taking cues from the overlords he idolized, Elias adopted an over-the-top persona, complete with dramatic monologues and theatrical schemes.

Yet even in Hell, Sir Pentine struggles. His inventions fail spectacularly, his plans backfire, and his reputation as a bumbling nuisance overshadows his dreams of grandeur. While he convinces himself he wanted power, he lacks the ruthlessness to pursue it. Deep down, Elias remains the same anxious, soft-hearted tinkerer he was in life, using his cartoonish villainy as a mask to hide his insecurities.

Despite his many failures, Sir Pentine clings stubbornly to his ambitions. Whether out of desperation, delusion, or sheer determination, he refuses to give up, convinced that one day he’ll finally prove his worth.

[sentientsliotar]

Hazbin Hotel Twister

Lucifer (who didn’t want to compete against Alastor’s tall ass): left foot red

Vaggie: this is a lot harder with wings

Husk with old man bones, wings, and tail: yeah seems like a real pain in the ass

Sir Pentinous: left foot- wait… wait what? How do I-

Egg Bois: We can be your feet boss!

Cherri Bomb: I’ll destroy all of you

Angel Dust: HA! Like ya have a chance against me!

Cherri Bomb: You are not using six hands in this game- where are the handcuffs?

Angel Dust: Kinky!

Alastor to Lucifer: In spite of that- I’ll participate. Seeing as this team building exercise is so important to to our dear Charlie

Alastor to everyone: but touch me and I’ll give a new meaning to the word twister

Niffty: *flings entire body onto the red circle and still doesn’t cover the space*

Charlie: I’m not sure I thought this all the way through

Keekee: *wins the game*

[rroketa]

theres like a hazbin hotel character that i think is real like in my sub conciousness but does not actually exist

he has like some 'wolf in sheeps clothing' dual personality where hes sweet to some people but a huge grumpy asshole to others. He wants to be Alastors assistant, and is really into heavy weaponry

hes grey and has like fox features?? Like not full-on furry. Kind of like Alastor where hes humanoid and just vaguely has animal features. def european

[vocalux]

If it’s not too much trouble but could I possibly request for a F/O flag of Sir Pentious from Hazbin Hotel? :}

Thank you so much in advance! 🐍🎩⚙️🥚

— sir pentinous f / o

a flag for individuals who have sir pentinous as f / o !

[sentientsliotar]

I thank you for this new headcanon

Hey, you guys remember that bit in the pilot where Sir Pentious thinks Angel Dust is his son? What if that's why he's at the hotel in the show?

He doesn't understand this whole "redemption" thing the hotel is selling, but he's here to be a good father and support his son's decisions like an overprotective soccer mom. Angel is deeply regretting he ever said anything while Alastor is actively encouraging the miscommunication because he thinks its hilarious.

[colourstreakgryffin]

Hello Hello!! I saw that you're taking requests? If it isn't too much trouble could I request something for a platonic Alastor x Tailor!Reader? Maybe being besties or gossip buddies? (Since I made an OC design based on ideas)

Oooh! I like this idea and to be honest, it reminds me of something I’ve been thinking about when it comes to Al; I made that one post of KNY’s Iguro Obanai with a Fluttershy! Reader and I have the extreme urge to see Alastor with a Rarity! Reader— but anyway. Let’s try this out

Alastor- Mischievous Rumours

“That’s when Charlie said ‘oh fuck you, Alastor. All you do is stand there, smiling while you watch us struggle and fail’. She’s such a fool for thinking I care for her and her friend’s helpless little struggles. Isn’t that delusional mindset so hilarious, my dear?” Alastor, the Radio Demon, laughs upbeat and eccentric with the radio effect deeply laced through his thick transatlantic accent voice chimes out as the grip on his signature staff-like microphone-cane seems to loosen. Standing completely still and on a nice marble pedestal, the deer Overlord spoke both mockingly and casually to the sweet kind tailor sinner, Leitora. A wonderful talented soul with the needle and thread, when it comes to tailoring coats like his own

“It definitely is, Al” You chime out softly and a bit distracted, hands wondering around the long torn rims of his red pinstriped coat. Only wondering in order to find the out of place tear that Alastor pointed out upon visiting your tailor shop. Some sinner named ‘Sir Pentinous’ had managed to tear off a bit of Alastor’s classic coat and as his most trusted tailor, it’s your job to take care of this little rip and tear within Alastor’s patience

The Radio Demon will not deny… he likes being up on this pedestal and his coat being touched, it makes him feel on top of Hell

“I know, darling. I find it so amusing that she believes I believe in her” This is a common thing Alastor did whenever he came to visit you for a hangout or when he needed you to repair his clothing. He loved to throw shade and shit at the Hotel staff and clients he surrounds himself. He loves to berate Husk for being incompetent, he loves to badly mock Angel Dust for flirting with him, he loves to mock and ridicule Vaggie, and he especially enjoys making fun of Charlie’s ‘delusional’ dream of redeeming sinners. You didn’t mind it, you find Alastor a funny man

“You’ll never believe in redemption, hey?” You also don’t mind snarking and teasing Alastor. He lets it slide with a natural toothy-less smile. His blood red eyes following the way you traverse over to the silver rack of many neatly organised rolled-up fabric bundles to pick out a perfectly shaded and patterned piece of crimson red fabric to begin sewing onto the obvious edge rip on the left side of his coat’s hems

This’ll be over in a few seconds but that doesn’t mean you won’t spend a whole twenty minutes with Alastor, spreading gossip around with him about sinners in your opposite ends. He’ll tell you about Overlords, you’ll tell him about the common Sinners. You like Alastor as a friend for a number of reasons, one of the main reasons being the mere fact you two can chat and gossip around, so fluently and naturally

“Believing in redemption is like believing a heart can beat without blood, darling. It’s just not possible. It’s foolish, mindless, sheltered. All adjectives to explain Charlie as a whole” Alastor is quite brutal with this and you can actually just sense the sourness pouring out of his voice and darker eyes as he speaks once more, his stance still well-mannered and classy but his gripping hand growing firmer, as if bottling up some type of anger deep within his soul. Deciding to not poke the sleeping deer any further, you effectively use your claws to trim off the rest of the string that tied the new fabric chunk onto his coat’s hems and repaired the tear to complete perfection

“Yes, Al. I understand, you are right in that sense”

Like a light switch upon hearing you agree, Alastor is instantly back to smiling more soft and caring with zero fangs visible than the very tense, passive-aggressive wide grin he had just painted on his face. Stepping down, rather gracefully, from the flat round multilayered pedestal, the Radio Demon readjusts his signature bowtie with a flick of his wrist. Sharp long red-tipped black clawed fingers dancing over his snazzy accessorises before facing you once more

He knows that new look of yours very well. A look of kindness and appreciation to see him once more but also urgency and duty. You’re busy and need him to leave but don’t want to say a word to avoid disappointing him

No, he didn’t like that whatsoever and he plans to be just a little bit selfish with one of his most favourites in Hell. He’ll have to take you away from your afterlife-stealing occupation so you can spend a day relaxing with him, drinking some nice warm tea and talking more smack about the people you two despise

Without even hesitating nor really thinking it over, Alastor locks his arm with yours and speaks once more, his kind and actually welcoming gaze and grin never once dropping as he begins to take charge, already deciding what’s going on for you today and he won’t hear you refuse such a idea

So… sorry, you’re gonna have to deal with it

“Darling. Don’t tell me you’re going to kick me out after this? How about you close up shop for today and we go out to a nice café? It’s been a while since it’s just been me and you”

[spopsalt]

Even though I admittedly really like the songs in Hazbin Hotel, a lot of them seem useless, since stans say it's meant to be watched like a broadway musical, I'll compare it to Heathers (Ik it's off broadway, but it's a musical so I'm counting it.) Let's compare some of the songs, I'll compare the first 4 of each to be fair.

Happy Day in Hell - Not the best song, but does an okay job of showing the setting

Beautiful - Really good song. Shows the setting, introduces the main characters (Besides JD) shows a massive plot point, shows the start of Veronica's conflict with her not liking her senior year of high school

Hell is Forever- Does an okay job at setting Adam as a villain, and admittidly gets stuck in my head a lot, even though Adam is a bad villian.

Candy Store - Really catchy. Sets up Heathers as villains, shows Veronica's inner conflict, and sets big plot point

Stayed Gone - Again, it gets stuck in my head. Does an okay job at setting up the conflict between Vox and Alastor

Fight for Me - Sets up Veronica wanting someone strong who will protect her, which comes up later in Dead Girl Walking Reprise where Veronica says "I wanted someone strong who could protect me" Sets up Veronica's feelings for J.D, shows her insecurity when Veronica says "When you face the crowd, could you be seen with me, and still act proud?"

It Starts With Sorry - Uhhhh I guess it uh...shows the dynamic between Sir Pentinous and shows the beginning of his (Mostly off-screen) redemption

Freeze Your Brain - Give JD more depth, shows JD's conflict, hints at his attraction towards Veronica, or at the very least that Veronica is special to him when it states (...) I don't learn the names, (....) You're planning your future, Veronica Sawyer

See anything different? Heathers songs sets up multiple things, while still being really catch, meanwhile Hazbinnnn a lot of their songs, while admittedly catchy, sets up one thing, two things if we're luckily, so they aren't all too plot important, what do you guys think?

[theyapper0]

Is the room next to the office as far from the other guests as possible Alastor's?

Ding ding ding!!! YEP!!!! Im so glad you got that!!!

Here's a little diagram on who's in which room!

**(The office is where Charlie and Vaggie are when they're working but not doing any redemption lessons)**

I wanted Alastor to be the furthest from the office to show the distance he places between himself and Charlie and Vaggie. ULTERIOR MOTIVES!!! SECRETS!!!! SUSPICIOUS!!!! hes so shady LOL

Husk and Niffty are in the rooms closest to his, they're under HIS contract and he likes to keep a close eye on them so it's safe to say that they did NOT pick which room they stayed in :)

Angel is the closest to the office because he's the Hazbin Hotel's first patron AND......... Charlie and Vaggie had to make sure to keep a close eye on him at ALL times HAHAHA! He's the worst

And Sir Pentinous' room is directly under the Hazbin Hotel sign as my subtle nod to showing he's going to be the first SUCCESSFUL patron!!! He's quite literally the FACE of redemption but more specifically, THE HOTEL, at the moment!

[jyoongim]

habit hotel finale

I just wish viv gave Alastor a fighting chance against Adam that was waaaaayyy to short of a fight scene.

ALSO ALASTORS LAST NAME HOW THE FUCK YOU SPELL THAT SHIT..

LILTH YOU BITCH!!!! sir pentinous you will be missed (him being in heaven is so funny hahaha)

daddy daughter duo really did that shit fr

[hazbin-mpreg]

Fun fact about my cherrisnake baby, also TW for brief mentions of egg laying- info below cut

So- Sir Pentinous actually carried their daughter (I have yet to name her tbh), considering she’s a snake like him- she was hatched from an egg (he was surprised- they thought she’d be a live birth), but he loves her anyway. After the egg is delivered he refuses to leave his nest, insisting on caring for the tiny egg ❤️

[autistic-ghost]

HOLY SHIT I HAD AN IDEA

they're in a hotel. In the mountains. It snows in the mountains.

I think you can see where this is going. The Shining style isolation, probably without the murder hungry ghosts but who knows??? It would either be pre canon or post canon (sorry sir pentinous ) to limit the character cast which will emphasis the theme of isolation. I might even exclude lucifer from this one, his powers would mean that the cast being trapped in the hotel wouldn't be a problem. I may even have to find a way to exclude Alastor from the hotel when they're snowed in, although I have more plausible denyablity with him. I don't think his power set would help much against a snow storm. I know I write stories with very heavy emphasis on the season it's taking place in because I enjoy it alot ( I love me my pathetic fallacy) and I have written a fic based in late spring, in late summer, one planned for Autumn (specifically the lead up to Halloween, can't wait for that one!) but no winter one yet. It would be an extremely character driven plot, probably standard ships (Caggie and huskerdust)(I have a fear of writing huskerdust I'm scared of messing it up but I might try. There's a lot of stuff I wanna try with the ship but I'm a little bit intimidated) in terms of pov I might actually try doing multiple different 3rd person closed perspective, maybe a new character every chapter but it might be cool to try do the omnipotent 3rd person (pretty sure that's what it's called but don't quite me) I don't think I've ever done it , not even when I was a lot younger messing about on Wattpad so it might be fun to try it

Also I will probably include ghosts. I'm a horror junkie at heart what did you really expect

[heavenboundhotel]

Hello, and welcome to the Heavenbound Hotel!

This is a Hazbin Hotel rewrite project I've been considering for a while, and I'm finally deciding to give it its own home to find like-minded people to possibly discuss my brainworms with!

I don't like Vivziepop or many things about the original but I consider myself almost a tentative fan, for all the issues I have I still hold a sort of nostalgia towards the fandom and enjoy a lot of the concepts and potential it has.

This is as much an exploration of Hazbin’s concepts as it is a sandbox for me to play with new ideas, characters, and storylines. While the project does keep some aspects of the original, a lot of my changes are intended to make the world and characters distinct from Hazbin—not everything here is necessarily an "improvement"; some ideas are just for fun or experimentation.

Keep in mind that Heavenbound Hotel is a work in progress! This rewrite is constantly evolving as I develop its lore, characters, and storyline. I’m open to suggestions, and I love engaging with others who are interested in reimagining Hazbin Hotel.

My main inspirations will be the original Hellaverse, as well as other biblical lore/demonology, fandom ideas and other rewrites, and my own ideas - and I'm open to suggestions and guidance!

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

HBH follows Lithop Morningstar, the stubborn and naive princess of Hell, daughter of the now-divorced Lucifer and Lilith and her attempts to redeem Hell's sinners. The hotel itself was opened shortly after Lithop, who had previously been shielded from them, discovered the yearly exterminations of sinners by Heaven. Her goal is to find a more peaceful alternative to control Hell's population, but its not as easy as she may have anticipated, almost seeming to cause more problems than it solves at first.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

CHARACTERS GUIDE:

Lithop Morningstar

Vera/Variel

Pixie Dust

Alistair, The Radio Demon

"Husker"/Hustler

"Nancy"/Nami

Cherry

Sir Pentine

[rainypixarcinemahorse]

Hazbin Hotel Anime style.

Here's the recast my version of Hazbin Hotel Fairy tail version .

Charlie Morningstar - Juvia Lockser

Vaggie - Lucy Heartfilia

Anthony "Angel Dust" - Natsu Dragneel

Alastor - Gray Fullbuster

Niffty - Wendy Marvell

Husk - Gajeel Redfox

Vox - Invel Yura

Sir pentinous - Jòse

Adam - Zancrow

Lucifer Morningstar - Zeref Dragneel

Lillith Morningstar - Mavis Vermillion

Rosie - Levy Mcgarden

Katie Killjoy - Minerva Orland

Mimzy - Risley Law

Cherri Bomb - Cana Alberona

Emily - Yukino

Lute - Dimaria

Sera - Selene

[zestialmorde]

hmm since I saw that you weren't sure about rating sir pentious

maybe I could send a photo of him and saw sum random facts about Him

(U DONT HAVE 2 RATE HIM IF U DONT WANT 2!!!)

- he is basically a cobra snake-sinner

- he died in the 1800s

- he is 40 years old

- He wears Victorian steam-punk clothes

- he is extroverted

- he used to be controlled by the one of the vees

That's all I know lol

(AGAIN YOU DONT HAVE TO RATE HIM IF U DONT WANT 2!!!!)

"Verily, it doth strike me that Sir Pentinous doth possess the semblance of a weakling. To be swayed by the Vees, of all people, speaks volumes of his character, or lack thereof. I find it rather astonishing that he hath endured for so long, given his origins in the 1800s."

[cottoncandiescupcakes]

Sir Pentious' name refers to Pentinence I think

Wiki says it's Prentenious or Pentagram but I don't think so

[wyllwithay]

Update on Character drag names:

So I think Karlach's persona will be Feeler Burns or Flaming Phister and Lae'zel would be Sir Pentine. Idk, king names are easier to figure out but I'm still struggling with Shadowheart.

I'm also thinking that Wyll will be a trans king who goes by Blade Frontiers or Frontiers Longblade something along those lines because I'm not feeling creative rn.

Lastly, Jaheira is a retired king who now rules the DJ booth with an iron fist.