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A cast of characters going up against Boyfriend, varying from cartoonish to comedic to demonic.Note 

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Main Weeks

    Cuphead 
https://static.tvtropes.org/pmwiki/pub/images/cuphead_ic.png
Good day for a swell rap battle.
Nightmare form 
Hey buster! You've got a lot of nerve messing with our land!
A cup headed boy prone to bad decisions and chaotic antics.
  • Adaptational Jerkass: Cuphead's original versions are much less prone to violence, with his game incarnation being forced into fighting the debtors and his show incarnation usually running away from a threat. He also swears in his Pre Ass Kicking One Liner before "Knockout", something neither canon version of Cuphead has done.
  • Blood Knight: He goes out of his way to antagonize Boyfriend and seems to be having a fun time fighting before he passes his Rage Breaking Point.
  • A Dog Named "Dog": He has a cup for a head. Guess what his name is.
  • Establishing Character Moment: Not for him, but for the Nightmare songs. "Devil's Gambit" starts with "Winter Horrorland's" Scare Chord as the game zooms in on The Devil slumped over on his throne, implicitly killed by Cuphead (unlike Cuphead, which just has him comically beaten up), as the camera zooms away to show Cuphead himself, completely black with glowing fuchsia eyes. This is an early sign that these songs don't star the trio as you know them.
  • Finger Gun: Weaponized as in the game, he uses the Peashooter and Chaser in gameplay, alongside the Roundabout's EX, Jumbo Rebound. Nightmare Cuphead even uses it to shoot the screen if you try to edit the chart of "Devil's Gambit".
  • Red Eyes, Take Warning: Cuphead's eyes are glowing fuchsia in "Devil's Gambit," his Nightmare song.
  • Self-Serving Memory: When he tries to remember Mugman's advice, he deliberately mis-remembers him stating that he's alright to beat up a boy with a red hat, blue hair and a white shirt.
  • The Juggernaut: In the fan animation, Indie Cross Aftermath, showing what happened before Devil's Gambit, his Nightmare form is shown to be this, easily curbstomping the Devil with extremely powerful and complex variations of his previous attacks, even managing to kill him with a point-blank shot from the Mega Blast ability, and no-selling nearly all of his attacks without a single scratch, quite the far cry from the Fragile Speedster that Cuphead usually is.

    Sans 
https://static.tvtropes.org/pmwiki/pub/images/sans_ic.png
i've gotten a ton of work done today. a skele-ton.
Nightmare form 
i know what happened with you and that cup guy. i'd say if you try to do the same with me... things won't turn out so well.
A lazy skeleton living in an underground civilization of monsters. He might just seem like a bad comedian at first glance, but don't piss him off unless you want to have a bad time.

    The Ink Demon 
https://static.tvtropes.org/pmwiki/pub/images/ink_bendy_ic.png
Someone has to keep the little devil happy...
Nightmare form 
The little devil darlin', not so darling anymore. A failed attempt at recreating the cartoon character Bendy in real life, the Ink Demon skulks the abandoned Joey Drew Studios.
  • Ax-Crazy: The most violent of the mod's antagonists by far, and Boyfriend witnesses this firsthand when Bendy brutalizes the poor boy after losing.
  • Battle Amongst the Flames: This happens during the near end of "Despair."
  • Berserk Button: Breaking Bendy cutouts really sets him off, as Boyfriend learnt the hard way.
  • Final Boss: To the main weeks and the mod itself, at least for right now, as the Bendy Week is the last week to be unlocked, and the Nightmare songs finish off with "Despair."
  • Flipping the Bird: Nightmare Bendy does this in his right pose.
  • Flunky Boss: He summons the Butcher Gang to help him in Last Reel, and he can unsummon them if he so wishes.
  • Foil: To Cuphead. Cuphead is the main protagonist of a videogame based on 30's cartoons which subsequently got a cartoon based off of it, while Bendy is the main antagonist of a videogame based on 30's cartoons who was based on a cartoon In-Universe. Cuphead uses far ranged finger guns, while Bendy usually gets close and personal when he wants to attack. Cuphead means no real harm in most of his actions and is just seeking fun, and while Bendy's original form was like this, his Ink Demon incarnation is nothing like him, aiming to attack those who step foot in the studio and being motivated by revenge and hatred.
  • The Fourth Wall Will Not Protect You: Just like Cuphead and Sans' Nightmare counterparts, Nightmare Bendy will reach out towards the screen if you try to edit the chart of "Despair". Uniquely though, Nightmare Bendy will do the same thing if you complete "Despair".
  • Glamour Failure: After losing in "Last Reel", Bendy's control over his form slips as he almost becomes Beast Bendy before attacking Boyfriend.
  • Glowing Eyes of Doom: Despite normally having an Eyeless Face, "DESPAIR" gives Nightmare Bendy a single twinkling eye as well as a glowing smile.
  • Knight of Cerebus: The Ink Demon isn't here to make jokes or have a fun time. He just wants to kill the Boyfriend, as shown by the fact that he beats the life out of him even after losing.
  • Ominous Obsidian Ooze: It's just ink, but that doesn't mean he's not dangerous. In fact, it might make him more dangerous than he looks.
  • Sliding Scale of Villain Effectiveness: The first two weeks star comedic relief, with Sans proving a much harder challenge than Cuphead if you antagonize him. Bendy, on the other hand, is entirely serious and the only one to leave major damage on Boyfriend. Also applies to his Nightmare song, a five minute long fight against a perfected Ink Demon.
  • Sore Loser: If he's beaten thrice, he just gives up on the whole thing and starts beating up Boyfriend. Taken further on Hard difficulty, in which he forces Boyfriend into a fourth song by giving chase.
  • Thinking Up Portals: Nightmare Bendy in "Sans VS Bendy" is shown generating portals. He generaly uses them to punch his opponent at a distance, but he also once uses one to swap places with Nightmare Sans to make his own attack hit him.
  • Unskilled, but Strong: He is this in general, but his Nightmare form in "Sans VS Bendy" especially places emphasis on "unskilled". He is extremely powerful, being capable of matching Nightmare Sans blow for blow and smack him all across outer space, but also has issues maintaining his form due to the possibility of overheating. This, mind you, is something no other Nightmare has to deal with, implying that it occurs due to him using too much power all at once.
    Hornet 
Yep. It’s the MC of the indie game Hollow Knight. She is an upcoming opponent for the main weeks, where she'll fight Boyfriend with her song, Silk.
  • Adaptational Badass: The devs are still working on a nightmare form for her.
  • Knight of Cerebus: Hornet isn't messing around with Boyfriend this time. She has a quest to complete. This is also taken literally given her role in her home game.

Bonus Songs

    The Devil 
https://static.tvtropes.org/pmwiki/pub/images/devil_ic.png
Anyone who opposes me shall be destroyed!
In case you ain't heard, I'm the Devil.
Old Scratch, Mister S, the Big D, he's the king of the underworld, yeah it's great to be him. Hasn't had great luck with collecting a certain cup's soul.
  • The Cameo: He can be seen in the background of Cuphead's Nightmare song "Devil's Gambit", slouched over and not moving at all. He appears to have been killed by Cuphead.
  • Flunky Boss: His henchmen will occasionally run into BF, damaging him if he doesn't dodge.
  • Satan: If you haven't noticed by now. He even has a Villain Song about it.

    Papyrus 
https://static.tvtropes.org/pmwiki/pub/images/papyrus_ic.png
He likes to say "Nyeh heh heh!"
NYEH HEH HEH!
Sans' much more energetic and enthusiastic brother. His biggest dream is to join the Royal Guard, and capturing a human will get him there! Don't worry, though. He wouldn't hurt a fly, but he would have it go through a labyrinth of poorly constructed puzzles.

    Sammy Laurence 
https://static.tvtropes.org/pmwiki/pub/images/sammy_ic.png
Sheep, sheep, sheep, it's time for sleep.
Those who mess with the Ink Demon... shall pay.
Formerly the song writer for Bendy cartoons, after ending up in the studios and being consumed by the ink, Sammy Lawrence devolved into a crazed cultist, with only the Ink Demon as his lord.
  • Badass Bystander: He's forced into this role during "Terrible Sin" and "Last Reel". He's handy enough with his axe to cleave a member of the butcher gang in two, but he can't assist his "lord" directly due to a mysterious barrier.
  • Badass Normal: Zigzagged. He's no cartoon, monster (at least literally), or demon, but once an average man cursed into an inky form. Aside from sharing the Ink Demon's ink notes, the only other Combat Pragmatism he's capable of is throwing his axe at BF by the end, which just as effective as the other's insta-kill attacks, which are more supernatural in nature.
  • Precision F-Strike: Lets out a censored one when his attempt at breaking the barrier separating him from the Ink Demon and Boyfriend falls flat.
  • Soft-Spoken Sadist: He sings so softly his song overtakes him at times.
  • Sophisticated as Hell: While normally a well-spoken Soft-Spoken Sadist, he lets out a bleeped-out Precision F-Strike after the barrier No-Sells his ace swing.
  • Token Human: Downplayed. He's the only human opponent in the mod. More specifically, former human, given what has become of him now.

    Cartoon Bendy 
https://static.tvtropes.org/pmwiki/pub/images/bendy_ic.png
I am alive! Immortalized! You're the creator, you traitor!
Let's hope this time we can get this band back together again!
The mascot of Joey Drew Studios himself. Oddly enough, he seems to already have some musical experience.
  • Friendly Enemy: During the first half of "Freaky Machine", he has a big, friendly smile on his face, he cheerfully says "You've got this!" halfway into the "Build Our Machine" section, and he lacks any gimmicks. Then again, he does go One-Winged Angel partway through the song, though this may just be for theatrics.
  • Power Floats: Starts floating after the Song Style Shift.
  • Red Eyes, Take Warning: As "Freaky Machine"'s instrumental shifts from "Build Our Machine" to "Instruments of Cyanide", his eyes glow red, and stay that way for the rest of the song.

    SPOILER CHARACTER # 1 

SANESSS

https://static.tvtropes.org/pmwiki/pub/images/saness_ic.png
DO YA WANNA HAVE A BAD TOM?
A deranged version of Sans that appears in the fake genocide ending. He uses Tom Blasters to attack as opposed to Gaster Blasters, and may be even stronger than Sans himself.

    SPOILER CHARACTER # 2 

The Horrible Goose

https://static.tvtropes.org/pmwiki/pub/images/goose_ic.png
Oh dear.
honk
A horrible, horrible goose that loves to steal and cause chaos. It's only natural they would choose to fight Boyfriend as soon as they saw him.

Other Characters

    Boyfriend 
The main protagonist who's dragged into a variety of worlds by (Presumably) Nightmare Girlfriend for an unknown reason.
  • Made of Iron: He remains relatively unharmed after falling for five minutes into the judgement hall (after a bit to dust himself off), and he managed to stand up and unleash a large scream without much difficulty after receiving a No-Holds-Barred Beatdown from the hands of Ink Bendy.

    Mugman 
Cuphead's brother, and the more level-headed and responsible of the two.
  • Only Sane Man: The only character in the mod to advocate against violence. Too bad he preaches this to his brother of all people.
  • Taking the Bullet: Unintentional example, as he ends up involuntarily taking a blast for BF that could have been completely avoided had he not showed up when he did. Boyfriend can do the same if he doesn't dodge.

    Frisk/Chara 
  • Omnicidal Maniac: As per usual, the fallen human embodies this. When possessing BF, they always start the song attacking with no input.
  • Red Eyes, Take Warning: Chara has these by default, and this carries over to Boyfriend while he's possessed by them.

    The Butcher Gang 
In the same way the Ink Demon was a failed attempt at making Bendy come to life, the Butcher Gang are failed clones of their original cartoon selves Charley, Barley and Edgar. The clones go by the names Piper, Fisher and Striker, and infest Joey Drew Studios in multitudes.
  • Flipping the Bird: Piper does this when obscuring the player's vision in Last Reel.
  • Support Party Member: Fisher takes a much different role to Piper and Striker in attacking, as he obscures the player's vision in Last Reel. Downplayed in Despair, as he actually attacks here, but is still functionally different to Piper and Striker.

    Jack 

    The Mysterious Figure 

Nightmare Girlfriend

A mysterious person whose only appearance was at the introduction video. According to an interview, they’re actually a nightmare version of Girlfriend.

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