A/N: This one took a lot longer to write than I thought it would, mostly because I kept procrastinating and focusing on A Nerd In Hell. Also not exactly happy with how it felt that I kinda following the script a bit too much; I do hope that I kept the Helltaker ladies in-character, though

I wonder how long it'll take for this fic to be discovered by the readers?


Chapter 1 – An Angel Arrives (Pilot)


Lucifer looked out the window of his palace as this year's extermination was coming to an end. He hated this time of year, not because of the exterminations, but because his daughter kept pestering him about wanting to end them. He just didn't understand what Charlie saw in these demons to make her think that they're worth saving.

It got to the point where she stopped asking him to do something, and to his frustration, started working on a hotel where sinners can be redeemed and go to heaven. In fact, she was supposed to announce her plans on the news later today. As he continues watching what's going on outside, he notices fireworks going off in the distance, knowing it's Charlie's work.

"That girl is just setting herself up for failure and disappointment," Lucifer says to himself before a knock on the door gets his attention. "Enter."

Lucifer's secretary walks in, a woman with small black horns and curly white hair tied in a ponytail wearing glasses and a black suit with a matching skirt. She was carrying a folder, and looked exhausted; of course that last part was not new. She was always tired unless she had her coffee, though she was only given the bare minimum required to keep her going. Lucifer was very strict with her supply given her sadistic tendencies when caffeinated.

"Ah, Pandemonica, what's planned for today?" he asks.

"Besides your daughter's big announcement on the news at 6:00, less than an hour, and a night out with Queen Lilith at 7:30; there's a new angel coming down today for the ten-year mission," Pandemonica answers as she hands him the folder. "Her dossier."

Lucifer could barely hold back the annoyed groan; this is one of the few things he hated more than extermination day. Every ten years, an angel is sent down from Heaven to monitor how things are going in Hell: Any change in the political climate, which demon managed to rise to Overlord status or fell from power, new alliances that formed or old alliances that fell apart, if Hell was making any plans to invade Earth or wage war against Heaven, if there was any work to solving the overpopulation, and so on. To make matters worse, he had to provide a safe house for the angel, with ten years' worth of supplies, and someplace remote enough where they wouldn't be bothered by any demons. Getting a dossier on the angel in question was the only thing he was able to get out of this; not that it helped much, since they were always old enough to remember his war against Heaven and his fall.

Opening up the file, he raised an eyebrow in mild surprise. This wasn't one of the older angels, the girl was just under two centuries old. He couldn't help but wonder what made the people up there send someone so young and inexperienced.

"Anything else I need to know?"

"Cerberus has been getting rowdy lately, you'll need to deal with them," Pandemonica answers.

"Fine. Notify me ten minutes before Charlie's scheduled to be on the news," Lucifer tells her as he starts heading out the room.

As he passes Pandemonica, he began to emit a bright glow that faded just as quickly, revealing him to have a new look. And a new gender. Now sporting long, loose white hair with similarly pale horns sprouting from her head, her top hat now a black spiked headband and her tux now a similarly dark business suit.

"That interview should be entertaining to watch, after all."

Pandemonica watches as Lucifer walks out of sight before she sighs, both from how tired she is and from Lucifer's attitude towards Charlie's redemption project. She was there when they had that argument, it was not pretty. "She could at least pretend to show support for her daughter."

And with that, Pandemonica takes out her phone to send Charlie a quick text. She might not believe redemption is possible, but she likes Charlie enough to show some level of interest. The princess knew how to make the perfect cup of coffee, after all.


Right after the final Exorcist enters the portal to Heaven, one angel exits just before it closes. She had short black hair and a white uniform with golden linings, and was carrying a tablet to use as a notepad.

Landing on one of the rooftops, Azazel looks at the surrounding area, almost in awe over the chaotic city around her. So much of the architecture in Pentagram clashed with each other, the buildings in one block looking like they were built a century before the buildings in the block right next to it. She wondered if it was built that way intentionally, or if it was because the city block with the newer buildings was destroyed and had to be rebuilt. Either way, it was a refreshing change compared to how orderly and uniform Heaven was.

She was always a curious angel, as long as she could remember, she wanted to learn as much as she could about demons and Hell. Unfortunately for her, there was very little information about demons that was available to low-level angels such as herself, and her curiosity about Hell lead to her being a bit of an outcast among her peers. But that didn't matter anymore, now it was just her observing these demons for a decade.

Technically, she was supposed to be heading to the safehouse that had been set up for her, but she figured that could wait for a little bit. Perhaps she can look down at the streets, see how –

She immediately regretted her decision to look, pulling back and vomiting on the rooftop from the horrific sight: The aftermath of the yearly cleanse.

"Good lord, is it always like this every year?!" she said in shock. The Exorcists were angels, how… how could they be so brutal? These may have been demons, but they were still people, right?

In a panic, she pulls up a big red button on her tablet, only to stop herself from actually pressing it.

"No. No! You are not calling for an emergency extraction, Azazel," she tells herself. "You spent years convincing your superiors that you were able to handle this ten-year mission; if you call to go home not even three minutes after arriving, you'll just be a laughingstock."

The angel cast a quick perception blocking spell on herself and took a look at her tablet. She remembered that her predecessor made notes about how the princess of Hell was planning something big that was to be revealed on the news, shortly after the yearly cleanse ended. At 6 PM, and it was approaching 5:10 right now.

"Okay, I have fifty minutes before I need to check out the news down here. Let's try the west side of the – "

A distant explosion interrupts her, and she sees an airship is laying siege to the west side of Pentagram City, and Azazel must be seeing things, because there's no way that she saw a figure in red use an explosion to launch themselves off a nearby rooftop to board the ship.

"– East side it is, then."

Wings of light materialize on the angel's back, allowing her to silently take off.

Azazel was glad, and slightly disturbed, that the demons were so efficient at cleaning up the mess.


Charlie : Thanks, Miss Monica. That means a lot. :)

Charlie sends the text to Pandemonica and was just about to turn off her phone when she just receives a text from her close friend, Modeus.

Modeus : Hey Charlie, good luck with the interview. We'll all go out to celebrate if you do well. If not, me and Verosika'll bring some ice cream over to the hotel to help you cheer up.

Charlie smiles at the text. While she knows that Modeus doesn't believe that redemption's possible, it still means a lot to the princess that she's getting support from her as well.

Charlie : Sure, that sounds fun. But nothing too crazy for the celebration, okay?

And with that, Charlie turns her phone off just as Vaggie turns away from the news set and walks up to her.

"Okay, you remember what to say?" Vaggie asks as she adjusts Charlie's bowtie for the twentieth time.

Charlie takes a deep breath before smiling brightly, "Yes! Let's do this."

Vaggie was a lot less confident, putting her hands on Charlie's shoulders, actually deflating the princess's optimism, "Just look at me, and I'll mouth it to you."

"Come on, Vaggie, I know what to say," Charlie says as she walks over to the nearby snack table. "I just feel like we need to...I don't know, make things sound more exciting!" An idea comes to her head, and she immediately back over to Vaggie. "Ooooh! What if I si– "

"Sing a song about it?" Vaggie asks, smiling as Charlie playfully boops her nose.

"You knew I was gonna say that!"

"Because I know you," she answers as she readjusts Charlie's bowtie. Vaggie's smile vanishes as she starts to gently shake her girlfriend, "But please don't sing. This is serious!"

"Well, you know, I'm better at expressing myself and my goals through song!" Charlie says, climbing up onto the table to pose. A pair of small goat demons watch as they munch on donuts, while Justice, Charlie's bodyguard and the former High Prosecutor, smiles at the sight.

Vaggie wasn't convinced, "But life isn't a musical, hon."

"Ah, lighten up, Vaggie. I'm sure Charlie'll do great," Justice says.

"But this is our only chance to make a good first impression for the hotel," the moth demon counters before turning back to Charlie. "We put a lot into it, you put a lot into it; and Killjoy is vicious, she'll tear you, and the hotel, apart the moment you start singing like a Disney princess."

"Fine. But I have these other ideas of what to say!" Charlie says as she hops off the table and hands Vaggie a paper, "The highlighted bits are the best part!"

"Uh, it's all highlighted," Vaggie says before taking another look at the list. "Is this a drawing?"

Charlie excitedly wraps an arm around her girlfriend, "Yes! That's the happy ending, see?! Everyone smiling and happy in Heaven!"

Justice snickers at how adorable and silly Charlie sounds. If it was anyone else, Vaggie would've just glared angrily at them, or punched their teeth in, but she knows Charlie's bodyguard enough to know that she'd never be mean-spirited towards the princess. Plus, Justice is blind, and much stronger than the moth demoness, meaning that the former wouldn't work and the latter is a bad idea. Instead, Vaggie just pinches her nose and focuses on her girlfriend, "I don't think it's that simple. Just please follow the talking points we went over." She grabs Charlie to look her right in the eyes, "And do not sing!"

Charlie just sighs a bit as she walks towards the news set, "Okay, fiiiine." The princess puts on another smile and starts speaking with a cute British accent. "I'll just have to resort to my impeccable improv skills!"

Vaggie crosses her arms as she watches Charlie go, worried about what might happen during the interview. Justice puts a reassuring hand on her shoulder, "Don't worry. As I said before, Charlie'll do great out there."

"How can I not worry about her? Just look at them," Vaggie says as she gestures to the crowd, specifically the bitch that's currently jabbing a bony finger into Charlie's chest. "You know that they'll just mock her if they can't take her seriously.

"They probably will, but that never stopped Charlie from doing what she loves. And she has us to support her with this."

"Yeah, she does," Vaggie says with a small smile.

"Plus, even if Charlie does sing, it's not like anything else will happen to hurt the hotel."

Vaggie's smile immediately vanishes, "And you just jinxed it…"


Azazel winces as she watches what's happening on the television, the news anchor demoness rushing back to her seat so fast that she literally broke her own neck from the whiplash. It did not seem to stop her, as she snaps her head back into place.

"Welcome back! So, Charlotte!"

"It's… Charlie."

The angel gasps as she sees the princess for the first time, she was equally adorable and beautiful. Azazel couldn't believe someone like her was the daughter of the most feared demon in Hell. Realizing that this was supposed to be her big announcement, Azazel takes out her tablet to record the broadcast.

"Well, as most of you know, I was born here in Hell and growing up, I always tried to see the good in everyone around me."

The anchorwoman stabs some kind of bug with her pen, splattering Charlie with its guts. Azazel grimaces as she watches the princess pause to wipe it off her face. As she continues, her tone becomes remorseful as she goes on about how many demons have been killed over the extermination, before getting hopeful as she brings up a way to end the exterminations for good. About a hotel to rehabilitate sinners so they can be redeemed and ascend to Heaven.

Azazel blinks in surprise, redemption for demons has been completely unheard of in Heaven. Granted, nobody has ever discussed a topic like that, but she is curious to see if Charlie has discovered a way to achieve this.

Almost immediately, Azazel frowns as she watches Charlie quickly lose the confidence she had moments earlier, and a nervous smile in its place.

"Y'know? 'Cause hotels are for people passing through... temporarily... I think it'll serve a purpose... a place to work toward redemption... yay...!"

The angel can't but feel disappointed. She doesn't know why, but for some reason, she wants Charlie to succeed with this. Because she saw the aftermath of the most recent extermination and found it too horrifying to have it continue? Because it'd create a new type of demon that angels like her can study for years to come? Because the princess is super adorable, and Azazel can't help but want to give her all the support?

She nearly laughs at that last thought. An angel supporting a demon just because she's cute? That's just ridiculous.

"Maybe I'm not getting through to you."

The sound of Charlie snapping her fingers snapped Azazel out of her thoughts, and she now sees the princess sitting on a piano played by a pair of small goat-like demons.

" I have a dream, I'm here to tell! "

Azazel spent the next two minutes watching, finding herself completely smitten with the princess. It was enough to make the angel completely forget that she's not to interfere, and convince her to help Hell's princess out with this noble quest. Wings of light materialized as Azazel takes off to find the hotel.

Unfortunately, the girl didn't realize that she hasn't been paying attention to what Charlie was saying when the singing started, and never found out the name of the hotel…


The front doors to the hotel slams open, allowing Angel Dust and Vaggie to enter the building, with Charlie and Justice following closely behind. The moth demoness angrily stomps her way to the lobby's couch while the spider strolls towards a refrigerator leaning against the wall. He grabs a half-melted popsicle before turning to Charlie as she sits on a large wooden crate.

"It's probably a good idea to get some actual food in this place. Y'know, to feed all the wayward souls you got in here!" Angel laughs at his joke, only to stop when he notices how hurt Charlie was over how everyone sees her and the hotel, and Justice just shakes her head at him. As Angel walks off, Charlie heads back outside, taking her phone out of her pocket as she exits.

"Well, that could've gone better," Justice says after a moment of awkward silence.

"You think?!" Vaggie responds angrily. "This was supposed to be Charlie's big day, but it all ended up being an absolute disaster. We're undoubtedly the biggest laughingstock in Hell by now!"

She groans in frustration, rubbing her forehead as she slumps against the couch, "I don't know how this day could get any worse."

"Hey, Vaggie?" Charlie interrupts.

"Whaaaat?"

"The Radio Demon is at the door."

Immediately forgetting her frustrations, the pastel goth girl sits up in a panic. "What?!"

"Uh… Who?" Angel asks.

Vaggie ignores him, "Well, don't let him in!"

Charlie turns towards the door, before heading over. She figured that there couldn't be any harm in at least hearing him out before turning him down.

"May I speak now?"

"You may," Charlie answers, and she's immediately greeted with his hand in front of her.

"Alastor! Pleasure to meet you, sweetheart!" The scarlet clad demon introduces himself, and pulls her in so that their faces are just inches apart. "Quite the pleasure!"

Alastor lets himself in before Charlie can stop him. "Excuse my sudden visit, but I saw your fiasco on a picture show, and I just couldn't resist! What a performance! Why, I haven't been that entertained since the stock market crash of 1929!" He laughs, "Sooo many orphans…"

Before he can take another step forward, Vaggie aims her spear right at his neck and pulls Charlie behind her. "Stop right there! Cabrón hijo de perra! I know your game and I'm not gonna let you hurt anyone here, you pompous cheesy talkshow shitlord!"

Alastor wasn't fazed by the moth demoness's threat. If anything, his predatory smile just grows wider, and he chuckles as he uses his finger to point her weapon away from him. "Dear, if I wanted to hurt anyone here..."

The overlord's eyes turn into radio dials and the world around them distorts heavily, "I would've done so already..."

The princess and her girlfriend look on fearfully as the distortion around them increases. "You aren't thinking of causing trouble, are you?" Justice interrupts, her arms crossed.

It was barely noticeable, but Alastor's eyes widen while his smile shrinks, and the distortions vanish as if they were never there. "Not at all, I'm here because I want to help."

Charlie and Vaggie stare at him in surprise. "Say what now?" the former asks.

Vaggie's surprise turns to skepticism as she crosses her arms, "You want to help? With what?"

Alastor appears right behind them, causing the two women to nearly jump in surprise. "This ridiculous thing that the princess is trying to do! This hotel! I want to help her run it."

The princess raises an eyebrow. "Buuut... why?"

Alastor laughs. "Why does anyone do anything? Sheer, absolute boredom! I've lacked inspiration for decades."

He uses Vaggie as an armrest, only for Justice to clear her throat. The crimson demon looks over at the bodyguard before he gets his arm off of the Hispanic woman's head.

"My work became mundane, lacking focus. I've come to crave a new form of entertainment!" he continues.

"Does getting into a fistfight with a reporter count as entertainment...?"

"It's the purest kind, my dear: Reality! True passion! After all, the world is a stage and the stage is a world of entertainment."

"So does this mean you think it's possible to rehabilitate a demon?" Charlie asks, a hopeful smile on her face that vanishes when Alastor laughs again.

"Of course not! That's wacky nonsense! Redemption, oh the non-existent humanity! No no no no, I don't think there's anything left that could save such loathsome sinners!" Alastor glances over at the couch, grinning at how Vaggie and Angel were offended by what he said. "The chance given was the life they lived before; the punishment is this! There is no undoing what is done!"

"So then, why do you wanna help me if you don't believe in my cause?"

As Alastor explains his reasons for helping out the hotel, Justice sits down at the couch. Angel seems to notice the tension. "So... What's the deal with Smiles over there?"

"Wait, you've never heard of him before?" Vaggie asks. "You've been here longer than me!"

Angel just shrugs.

"The Radio Demon. One of the most powerful beings Hell has ever seen?"

"Eh, nothing more than some upstart," Justice retorts. "He clearly hasn't changed after all these decades."

"Wait, you met him back then?" the moth demoness questions.

"Met him? Who do you think stopped his carnage?"

"No way, you're the Radio Killer?"

Justice chuckles, "That's what they're calling me? That's as lazy as how the Radio Demon got his name."

Angel laughs. "You're tellin' me that this blind lady beat the shit out of the strawberry pimp?"


The past couple hours have been exhausting for Azazel. She'd been flying around the entire city, checking out nearly a dozen hotels only to discover that Charlie wasn't associated with any of them. It was at that point that the angel realized that she never actually learned what the princess's hotel was called. With that, she flew onto a rooftop so she could watch the recorded interview. It took watching that song four times for Azazel to finally focus long enough to learn what the place was called.

The flight to get from the rooftop to the hotel is only a few minutes, and Azazel's quite excited to see this hotel for herself.

That excitement quickly turned to horror as she sees the airship from earlier be destroyed like it was nothing by what she can only describe as some tentacled monstrosity. The red demon who summoned it looked as powerful as he was terrifying, and he was terrifying enough that Azazel was very tempted to just forget everything and fly away.

But… Someone made her stay…

As the group of demons started to head back into the hotel, the angel's eyes were drawn to the grey-skinned woman standing next to the princess. After a moment, Azazel's eyes widen as she recognizes her. Different skin and hair color, and the eyepatch is new, but she definitely recognizes the demoness. "It can't be…"

As they all turn to walk back to the hotel, Azazel flies down and lands behind them. "Vaggie?"

The two demon women stop mid-step, and Azazel freezes as she notices that they heard her. They shouldn't be able to hear her; she still has her perception blocking spell up. It wasn't perfect, sure, but it still should've been enough to ensure that no demons would ever notice her.

Vaggie whips around, spear already drawn and ready to skewer in case it's a threat, only to lower it in surprise when she sees who said her name. Charlie turns around too, and gasps in surprise at the sight of an angel.

"Azazel?" the Salvadoran woman asks.

"You know her?" Charlie questions.

"Yeah, she was my best friend. Back before I fell, when I was still an angel."


A/N: I'm honestly shocked that there aren't any more Hazbin Hotel x Helltaker fics. I'm sure that there's only just one other one on AO3, which is weird, since there's so much potential with the two series together.

I kinda have an idea on what roles some of the Helltaker girls would have, but I'm completely clueless about Cerberus, Malina, Zdrada, Judgement and Beelzebub. The author of the other HH x Helltaker fic was able to provide some ideas on what their roles could be, but I don't have anything concrete yet. So feel free to pitch in suggestions if you have any

Also, I'm not sure if/when I'll continue this, since most of my attention is on A Nerd in Hell


Helltaker girls' roles

Lucifer – The exact same. Lucifer is genderfluid and sometimes turns himself into a woman for various reasons.

Pandemonica – Lucifer's secretary. Has a bit of a soft spot for Charlie because the princess is able to make the perfect cup of coffee for her, though she will deny it. Think of their relationship as being like how Pandemonica is genuinely friendly towards the old man who ran a café in the Helltaker comic.

May or may not become a part-time receptionist for the hotel; though if she does, Alastor will learn to fear her

Cerberus – Lucifer's pet. Role N/A

Azazel – An angel sent from Heaven to monitor Hell for the next 10 years. An outcast because of her interest in demons, an interest that seemed to go further than simply studying them, Vaggie was her only friend. She was going to work up the courage to ask Vaggie out on a date when she returned from the 2015 cleanse, unaware that fate planned for Vaggie to fall for someone else instead.

Because of how dangerous the ten-year mission is, angels who are assigned the task are required to learn a perception blocking spell, making it so that demons cannot see, hear, or feel their presence in any way, and Azazel is no exception. However, since she hasn't perfected the spell, those with angelic backgrounds can see her. Charlie and Vaggie can still see her due to the former being half-angel and the latter being a former exterminator.

Despite Azazel's mission requiring her to monitor and not interfere, she seeks to help the hotel in any way she can. Because it's a good and just cause, and definitely not because she finds Charlie to be super adorable.

Modeus – Daughter of Asmodeus, making her the princess of the Lust Ring. A few decades younger than Charlie, they basically grew up together. While still lustful, she's become quite wholesome and loving due to being alongside Charlie while growing up. She's currently in a relationship with Verosika, meaning that the succubus is not the bitter alcoholic she is in Helluva Boss; though Verosika's still harboring a lot of anger towards Blitzo for what he did.

Modeus absolutely loathes Valentino, who she sees as the absolute worst and a perversion of lust. The mere sight of him is enough to get Modeus to chase him down with her sledgehammer

Justice – Former High Prosecutor, a rank that's both a high general of Lucifer's army and head of what could be seen as Hell's equivalent to law enforcement, and currently Charlie's bodyguard, though she only gets involved whenever the goat bois and Vaggie can't handle a problem. Since problems like that are rare, Justice spends most of the time as Charlie's "cool aunt".

Freakishly strong, her strength rivaling that of Queen Beelzebub, Justice is one of the few demons that Alastor truly fears.

Malina – N/A

Zdrada – N/A

Judgement – Current High Prosecutor. Role N/A

Beelzebub – One of the Seven Deadly Sins, and the Queen of the Gluttony Ring. Role N/A