1 - 20 of 50 Works in Rolando (Helluva Boss)
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Ask The Fallen by WholesomeHazbin
Fandoms: Hazbin Hotel (Cartoon), Helluva Boss (Web Series)
14 Dec 2025
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Summary
Charlie Morningstar is the Princess of Hell at day, by night she becomes the Fallen. But here, she'll answer your questions.
For any questions you have for Charlie/Fallen, her friends, or adversaries, feel free to ask them here.
(AU's and one-shots will be commissioned as well)
Series
- Part 2 of The Shadows of Hell
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The Fallen: Game Over Scenes by WholesomeHazbin
Fandoms: Hazbin Hotel (Cartoon), Helluva Boss (Web Series)
12 Dec 2025
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Summary
Various game over screens with the characters in The Fallen series.
All show alternate outcomes, resulting in Fallen, or others, winding up dead.
Series
- Part 4 of The Shadows of Hell
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Opened by Your Five Senses by CommaSeparated_Value
Fandoms: Helluva Boss (Web Series), Hazbin Hotel (Cartoon)
04 Dec 2025
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Summary
The Queen of Gluttony deals with the aftermath of the shotgun marriage between the worlds of the living and the dead.
With nothing separating humans from accessing the world of the afterlife, Beelzebub has much more to do once again than just keep the lights on at her parties...
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The Story of Ellie by KateCrane37
Fandoms: Helluva Boss (Web Series), Hazbin Hotel (Cartoon)
03 Dec 2025
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Summary
Charlie comes by Stull and she brought her friends with her. When Angel asked what makes her hotheaded after an incident at a bar, Kate opens up to them about the trauma she and her mom went through, with a certain fish listening on them.
Series
- Part 6 of D-Huntz: A Helluva Series
- Language:
- English
- Words:
- 4,126
- Chapters:
- 7/?
- Hits:
- 23
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Verosika Mayday & Sallie May Vs the pink baby devil of trouble by Golden_devil
Fandoms: Helluva Boss (Web Series)
28 Nov 2025
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Summary
when Verosika got kicked out of her apartment for not paying her bills. (As well as being secretly being sued by Tiffany Titfucker). She thought that she was going to spend the rest of her days alone. So what if she finds a tiny strange baby hiding among the bins, outside of where she was?.
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Allie's Awesomeland by animechess69
Fandoms: Hazbin Hotel (Cartoon), Helluva Boss (Web Series)
28 Nov 2025
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Summary
Husk expected just a night of cleaning up an entertainment center that's going to be reopened. He never asked for a rebellious teenage girl and her friends trying to get him to leave the building, the policewoman and her partners-in-crime who traps him in there to begin with, and to be told the horror story of the town. Oh, and entertainment robots that are trying to kill him, he definitely never asked for that
Series
- Part 28 of Parodies and Rewrites
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The Fallen by WholesomeHazbin
Fandoms: Hazbin Hotel (Cartoon), Helluva Boss (Web Series)
22 Nov 2025
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Summary
During the nights in Hell, a savior is flying through the skies and watching from the rooftops across Pentagram to keep the good citizens free from evil.
The Fallen.
Someone who wears the uniform of an Exorcist, but bears no halo. The only rule she follows is "No Killing."
Nobody knows their true name, but when the morning comes, Fallen wears the mask of Charlie Morningstar, Princess of Hell.
But how long will it be before someone discovers Charlie's secret?
And how long will it be before they break their only rule?
(Hazbin Hotel Batman AU, with Charlie taking on the role of Batman)
Series
- Part 1 of The Shadows of Hell
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HELLUVA LOSS: ROLANDO'S RAMPAGE (Halloween Ghostfuckers 1 year special) by HelluvaScribe
Fandoms: Helluva Boss (Web Series), Hazbin Hotel (Cartoon)
31 Oct 2025
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Summary
Happy Halloween…or should I say Unhappy Halloween. It’s been one year since Ghostf***ers came out and no Rolando merch has been seen since. He’s double dead to the Helluva Boss fandom now, while every other character continually gets merch, even Chaz who was a one-off villain like Rolando. The merch is a mess, especially now, and Helluva Boss is a shell of its former glory. Inexcusable and disrespectful. That’s why I made this in frustration…because in my opinion, no other character in the show can out-shadow this underrated villain. Enjoy this Rolandoween special…or don’t.
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Just like the HELLUVA SHORTS…but featuring Rolando…
Before Rolando’s electrifying death at the One Star Wonder Hotel, many other events brought him there. Immersed in the power-hungry, envious culture of Envy, Rolando experienced an endless battle to rise in the ranks, seek status and feast on as much negativity as possible (not his own, of course!) Dive into the depths of this underrated villain’s backstory…if you dare.
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(Takes place after the Apology Tour) It has been a month since the I Hate Blitzǿ party, and things aren’t going well for the assassin. Things only get worse when an infestor demon develops a taste for his sadness and his deep self-hatred. Plagued by nightmares fuelled by the power of this demon, his team turn to the only one who can possibly save him, Stolas.
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Ellie’s Inner Mind by KateCrane37
Fandoms: Helluva Boss (Web Series), Hazbin Hotel (Cartoon)
14 Oct 2025
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Summary
After reading the Blackout Journal, Andrealphus orders Rolando to go into Ellie’s sleeping mind. From there, Rolando discovers secrets about Ellie…and realizes why his chest flutters.
Note: This work contains sex scenes and scary images of the mind. Reader discretion advised.
Series
- Part 5 of D-Huntz: A Helluva Series
- Language:
- English
- Words:
- 4,806
- Chapters:
- 7/7
- Hits:
- 39
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Summary
After his defeat by Blitzo and Millie, Rolando reacts to the Helluva Boss episodes...
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Helluva Boss: The Great Pirate War AU - The Sinister Siren by HelluvaScribe
Fandoms: Helluva Boss (Web Series)
23 Sep 2025
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Inspired by the Great Pirate War AU Merch drop on August 18, 2025. Fueled by my rage of not seeing my favorite underrated villain Rolando part of the merch drop YET AGAIN! Another missed opportunity. I could’ve called it “Legend of the Golden Grimoire” or “Helluva Captain” or “Blitz’s Buccaneers” or just “The Great Pirate War,” but Rolando deserves to be in the title, so there.
Created August 18 – August 31 2025
Warning: “Helluva Boss The Great Pirate War AU” contains violence, drinking and sexual references, no modern swearing and Rolando. Viewer discretion is advised.
Series
- Part 1 of HELLAVERSE GREAT PIRATE WAR AU
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For BurntPopcorn and TallestMaraji
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It is time for the Harvest Festival in Stull, and Rolando asked Ellie to the carnival. At first it goes well, but weird accidents began happening to Rolando every time his human persona gets too close to Ellie. To make matters worse, the bounty hunters that tried to get them both are back, and one of them knows Via.
Series
- Part 4 of D-Huntz: A Helluva Series
- Language:
- English
- Words:
- 3,959
- Chapters:
- 8/8
- Hits:
- 46
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Summary
Totally *not* inspired by the official Helluva Boss Prime trailer. New episode around the same time as Mission Zero and more to follow.
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Hazbin Bosses - A Hazbin Hotel and Helluva Boss Crossover by HelluvaScribe
Fandoms: Helluva Boss (Web Series), Hazbin Hotel (Cartoon)
20 Sep 2025
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Summary
Two series collide! Charlie helped save the hotel from the Exorcists and Adam. With more clients coming in, her business appears to be in full swing. But her leadership is soon put into question when a prominent I.M.P. assassin Blitzo comes over. He’s not happy with the thought of potentially losing more clients to Heaven. Vaggie tries to smooth things over, while many other characters meet. Moxxie and Angel Dust discuss their shitty mafia families, Millie, Vaggie and Niffty practice their warrior skills and even Loona, Octavia, and Crymini find similarities through music and their own darkness. But not all is sunshine and rainbows: the Vees, threatened by the loss of their status, have plans to humiliate the Hazbins. Lute vows to get revenge on the loss of her leader. Alastor has his own shady plans…and a mysterious villain longs to feast on everyone’s greatest fears. Can Charlie save her people and unite her friends in time?
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Thanks to a very nasty infestor demon slipping his way into Stolas's dreams, it's up to the circus trio to rescue him before it's too late.
Series
- Part 175 of Blitz/Stolas Happier Childhood Memories
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Infamous infestor demon Rolando has no theme song...how disappointing...
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Rolando Infests Every Character - Season Two by HelluvaScribe
Fandoms: Hazbin Hotel (Cartoon), Helluva Boss (Web Series)
17 Aug 2025
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Summary
Hazbin Hotel edition...
Series
- Part 2 of Rolando Infests Every Character