1 - 20 of 50 Works in Rolando (Helluva Boss)

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  1. Tags
    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
    Language:
    English
    Words:
    11,949
    Chapters:
    80/100
    Comments:
    204
    Kudos:
    56
    Bookmarks:
    6
    Hits:
    2,786
  2. Tags
    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
    Language:
    English
    Words:
    1,996
    Chapters:
    10/?
    Comments:
    34
    Kudos:
    9
    Bookmarks:
    4
    Hits:
    562
  3. Tags
    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...

    Language:
    English
    Words:
    30,436
    Chapters:
    19/?
    Comments:
    25
    Kudos:
    12
    Bookmarks:
    4
    Hits:
    1,112
  4. Tags
    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
    Language:
    English
    Words:
    4,126
    Chapters:
    7/?
    Hits:
    23
  5. Tags
    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?.

    Language:
    English
    Words:
    15,352
    Chapters:
    11/11
    Comments:
    10
    Kudos:
    10
    Bookmarks:
    1
    Hits:
    892
  6. Tags
    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
    Language:
    English
    Words:
    29,122
    Chapters:
    37/?
    Comments:
    44
    Kudos:
    6
    Bookmarks:
    1
    Hits:
    1,077
  7. Tags
    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
    Language:
    English
    Words:
    17,255
    Chapters:
    16/?
    Comments:
    82
    Kudos:
    74
    Bookmarks:
    20
    Hits:
    3,412
  8. Tags
    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.

    Language:
    English
    Words:
    33,657
    Chapters:
    10/10
    Kudos:
    1
    Hits:
    193
  9. Tags
    Summary

    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.

    Language:
    English
    Words:
    13,674
    Chapters:
    4/4
    Comments:
    2
    Kudos:
    2
    Bookmarks:
    1
    Hits:
    120
  10. Tags
    Summary

    (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.

    Language:
    English
    Words:
    15,048
    Chapters:
    13/13
    Comments:
    38
    Kudos:
    116
    Bookmarks:
    29
    Hits:
    3,404
  11. Tags
    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
    Language:
    English
    Words:
    4,806
    Chapters:
    7/7
    Hits:
    39
  12. Tags
    Summary

    After his defeat by Blitzo and Millie, Rolando reacts to the Helluva Boss episodes...

    Language:
    English
    Words:
    30,089
    Chapters:
    9/?
    Comments:
    1
    Kudos:
    6
    Hits:
    366
  13. Tags
    Summary

    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
    Language:
    English
    Words:
    23,999
    Chapters:
    5/5
    Kudos:
    7
    Bookmarks:
    5
    Hits:
    691
  14. Tags
    Summary

    For BurntPopcorn and TallestMaraji

    Language:
    English
    Words:
    7,498
    Chapters:
    1/1
    Kudos:
    1
    Bookmarks:
    1
    Hits:
    46
  15. Tags
    Summary

    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
    Language:
    English
    Words:
    3,959
    Chapters:
    8/8
    Hits:
    46
  16. Tags
    Summary

    Totally *not* inspired by the official Helluva Boss Prime trailer. New episode around the same time as Mission Zero and more to follow.

    Language:
    English
    Words:
    2,398
    Chapters:
    3/?
    Kudos:
    2
    Hits:
    39
  17. Tags
    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?

    Language:
    English
    Words:
    7,957
    Chapters:
    2/?
    Comments:
    1
    Kudos:
    8
    Bookmarks:
    4
    Hits:
    595
  18. Tags
    Summary

    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
    Language:
    English
    Words:
    10,645
    Chapters:
    5/5
    Comments:
    25
    Kudos:
    19
    Bookmarks:
    5
    Hits:
    851
  19. Tags
    Summary

    Infamous infestor demon Rolando has no theme song...how disappointing...

    Language:
    English
    Words:
    1,783
    Chapters:
    5/5
    Kudos:
    1
    Bookmarks:
    1
    Hits:
    41
  20. Tags
    Summary

    Hazbin Hotel edition...

    Series
    Language:
    English
    Words:
    17,344
    Chapters:
    2/?
    Comments:
    1
    Hits:
    238

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