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As this is a WMG page, all spoilers will be unmarked ahead. You Have Been Warned!


For theories on The Cuphead Show!, click here.
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    Pre-release 

The Devil's gamble was rigged.
Whatever game they were playing, he rigged it so that Cuphead and Mugman would have to submit to him. Satan is known for his love of deception, so it would only make sense for him to cheat at the game, especially considering that it would put Cuphead and Mugman at his mercy.
  • Confirmed!

...But that's not the only way that Cuphead and Mugman are being fleeced.
The Devil isn't sending them to fight these dangerous bosses for a good reason — he just wants to watch them suffer, and he isn't betting on them succeeding. And when they succeed, hopefully his reaction will be a sight to behold!
  • There could be a psychological aspect as well, with some of the bosses having either made deals with the devil before for very sympathetic reasons and/or out of desperation or had nothing to do with anything until the Devil sicced the PCs on them and they are just defending themselves. Revelations like these will definitely weigh heavy on the PCs consciences and the Devil will laugh at their anguish.
  • With their angry glares and taunting death messages, I think we're meant to assume that the bosses are Asshole Victims. But it would be interesting if they turned out to be more sympathetic than they seem. Who knows, maybe even the Devil will turn out to be not such a bad guy? If not, it would still be cool if Cuphead and Mugman managed to turn all the bosses against the Devil.
  • Speaking of the psychological theory above, it's also possible that if Cuphead and Mugman do actually complete their task and pay their debt, The Devil can pull There Can Be Only One on them and force them to fight each other, only letting one of them off the hook.

There will be singing at some point.
Wouldn't it be awesome if the final boss sang a Villain Song, complete with Cab Calloway's dance moves, in an arena where Everything Dances?
  • Maybe not everything described here will happen, but according to an interview with the composer, Calloway was a big influence on the game's soundtrack, so... maybe.
  • Confirmed! Die House is a Villain Song sung by King Dice, and it sounds pretty Calloway-esque. As to whether or not the final boss will sing is still up in the air, but at least we have this!
    • ...Except that the final boss kept his mouth shut, meaning that that part of the theory is Jossed.
    • The Devil finally got a Cab Calloway-esque villain song in The Cuphead Show!, though.

May overlap with the above theory. This would be pretty cool, too.
  • Although it isn't associated with the final boss at all, "The Mausoleum" does indeed feature Ominous Pipe Organ, although it's unknown whether or not that's a theater organ playing. In the credits, the organist is simply credited under "Organ".

The Devil will be the Final Boss.
It seems way too obvious, but that's just how we like it. Cuphead and Mugman get fed up with the Devil and, feeling (rightfully) confident in their skills and burning with anger, they decide to go up to the big D himself and blast him to kingdom come.
  • Based on these images, that sounds very likely.
    • Confirmed; the Devil is the final boss, first at his more earthly throne, then in Hell itself.

Going off of the above theory, there will be Multiple Endings.
The Bad Ending will involve Cuphead and Mugman becoming just as bad as the Devil and taking over Hell. As for the Good Ending... maybe Cuphead and Mugman free everyone who's indebted to the Devil? Which ending you get may be determined by the difficulty level you choose.
  • Heavily implied by the revealed achievement list. There are different achievements for beating the game on Normal or Expert difficulty, so it's very possible that there will be multiple endings depending on the difficulty. However, the achievement for Normal is called "Souls Saved". That sounds pretty good, so perhaps there won't be a bad ending, just a good ending and a Golden Ending.
    • Confirmed in general, including the theory's idea of what the good ending will be like. However, the following bits of the theory have been jossed: Rather than flat-out taking over Hell in the bad ending, Cuphead and Mugman become the Devil's servants. Also, there IS a bad ending and the closest thing to a Golden Ending is the default good ending, where the debtors are freed, and the difficulty level doesn't affect the ending you get so much as how it is affected by the duo's choice of handing over the contracts or not (except for the fact that neither of the two endings can be achieved in easy mode).

If the Devil is indeed the final boss, he will use some gambling-themed attacks.
Although it's more likely that his moves will mostly be fire-based, it would be interesting if he used some casino items to attack, as kind of an Ironic Hell considering the gamble Cuphead and Mugman lost to him.
  • Confirmed with respects to his second phase's ability to drop huge flaming poker chips on Cuphead and Mugman. Most of the gambling stuff in the game is unleashed by King Dice, however.

Cuphead and Mugman are acting as reapers for The Devil.
By all appearances, all the bosses aren't good guys; in fact, they're villains. The Devil makes the two reapers to go collect on some sinners. It's sort of an 'X amount of souls in exchange for yours' kind of deal.
  • Confirmed! The brothers need to collect contracts being held by each boss, though the Devil has no intention of holding up his end of the bargain and — in the good ending — Cuphead and Mugman destroy the contracts and save all of their souls.

Peacock will be a DLC boss.
Considering she's basically designed to look like an old cartoon and her fighting style is cartoon violence incarnate, she definitely wouldn't be out of place. Her final form may even be her Super Form which was only in the planning stages.
  • Jossed since there's no DLC.
    • ...Until now. But still, every boss is an original character.

If not Peacock, it will be Bendy.
After all, he's the star of another video game revolving around the Inkblot Cartoon Style. It helps that the two games' fandoms are both, for the most part, on good terms with each other. It could also be interesting because this game has its own cartoon devil.
  • Jossed due to the same reason as the above theory.

The dice-headed man in the E3 2017 trailer.
At the end of the new trailer, we see a new character, a guy with a die for a head, wearing a gold suit. Some theories on who he is:
  • The Big Good. He's shown standing opposite from the Devil, and he has mostly bright colors. Maybe he's a friendly gambler helping Cuphead and Mugman pay off their debt?
    • Jossed.
  • The Dragon to the Devil. Maybe he's an Anthropomorphic Personification of the evils of gambling?
    • Confirmed. Die House has it outright state that the dice-headed man, King Dice, is the Devil's right-hand man.
  • Maybe he's just the announcer for each battle, although this could overlap with one of the above two.
    • Jossed.

There will be an entire casino-themed world or map.
The level with the two frogs who turn into a slot machine doesn't seem to be on the forest-themed map we've seen thus far, and we've seen quite a few other casino-based characters and bosses in the trailers (The dice-headed man, the dancing roulette wheel girl, etc.), so maybe they'll get a map all to themselves. It would make sense considering that gambling is what landed Cuphead and Mugman in trouble in the first place.
  • If there is such a map, the part about the frogs being there is jossed. Their level is on a boat found at the edge of the forest map.
  • One of the leaked achievements is "Casino Night: Complete the Casino", so this is more or less confirmed. However, it remains to be seen what exactly the casino level will be like, and if it's treated the same as the other maps.
    • Semi-Confirmed: Although the Casino is technically a Boss Rush (with King Dice as the Pre-Final Boss), it is definitely a casino-themed world.

The final phase of the final boss battle will be a shoot 'em up.
Whether or not it's the Devil himself, in the final phase, the boss will take to the skies, forcing Cuphead and Mugman to finish the battle in their planes. It would make for a good Final-Exam Boss.
  • Jossed: It's only a regular stage.

At some point, King Dice was indebted to the Devil too.
But rather than follow the Devil's instructions and take the honest way out, King Dice attempted to manipulate and negotiate with the Devil. The Devil realized that King Dice was just his kind of guy, and allowed him to work for him as an honored servant.

Following up from the above theory, the Devil's ultimate goal is to turn Cuphead and Mugman evil.
That's why he's sending them to fight all these monsters and crooks — since they didn't sell out to him as King Dice did according to the above theory, the Devil hopes that the thrill of fighting will turn them rotten too.

If the above two theories are true, then the game's story will be a commentary on the making of the game itself.
King Dice represents soulless corporations that make games solely for money, with little consideration for anything else. Cuphead and Mugman represent Studio MDHR, who started at the bottom but managed to succeed in realizing their dream by putting in intense amounts of work. Even when they received backing from Microsoft (Pork Rind and other allies), they still did work that most people wouldn't have the patience to do. And for that reason, they will succeed where some other games fail.
  • Jossed.

Alternatively, the game itself won't have much of a plot.
The emphasis will be almost entirely on gameplay, which, to be fair, the devs seem to have gotten down solid. If this is true, maybe these theories will be confirmed or Jossed in other sources.
  • Jossed.

    Post-release 
The Bosses got their powers from the Devil.
All the powers they use are ones they got from their deals with the devil, but since they feel powerful and confident, they refuse to pay their side of the deal. The Devil sends Cuphead and Mugman because he feels it is a win-win for him: if they succeed, his debtors have to pay, and if they lose, he gets to keep them instead.
  • They do all have a state where they go "crazy" and become particularly more monstrous or demonic and seem to have some ability to pass this demonic state to other beings like the Baroness does to her castle. Some of them seem to even unwillingly undergo a transformation like they lost control over their own powers (most clearly seen with Hilda Berg).
  • The only one to subvert this idea is Sally Stageplay. She fights with props from her play and cardboard cutouts. Perhaps she sold her soul for insane acting skills?

Related to the above: the other, unstated half of the deal is that it brings out the worst in the debtors.
Either implicitly, by putting them in an awful situation to make them squirm, or explicitly, a la Brainwashed and Crazy. Nearly every single one of the bosses (the only exceptions being Weepy of the Root Pack and Werner Werman) spend some portion of their boss fight wearing gigantic, psychotic-looking smiles. Also implied by the good ending, where the majority of the bosses show up and celebrate Cuphead and Mugman's victory, now that they're free of their debts.

Related to that above, the soul contracts are actually corrupting the debtors.
It explains why several of the debtors act and appear so cartoonishly evil in their boss fights and defeat portraits. Those cheery, happy bosses seen in The Good Ending where the contracts are burnt heavily imply that they’re mostly good people, or at least are very happy for the accomplishments of the brothers. Grim Matchstick may act nice in his death quotes because his soul contract has yet to fully corrupt him (and he is the last boss on the list for Isle 2, maybe he got his contract late?). This also explains why The Devil hasn’t gone after these debtors himself. If these bosses are becoming evil the longer they hold onto their contracts, then eventually they can bring some chaos to Inkwell Isle, giving him a pleasure to watch. People trying and failing to fight these debtors and/or gain their contracts can serve as entertainment for him too. And if The Devil does get the soul contracts back, he gets to control these bosses, as well as the one(s) who brought them in if the Bad Ending is anything to go by.

An [adult swim] series will be made based on this game.
Self-explanatory, really. Let's just wait and see.
  • If there is one, it will more likely be a family series, since this game has an "E" rating in North America.
    • "Family series" my butt. After all, with all the tobacco and alcohol references, gambling references, garbage like that, and the Devil himself, how did this manage to get an E rating??!!
      • Animation Age Ghetto.
      • That and universally none of those things are considered child-inappropriate. Children's animated shows have gotten away with that and much worse, not sure why the surprise.
      • Are we forgetting all the stuff Disney got away with in Pinocchio?
  • Jossed. It's coming to Netflix instead.

Grim Matchstick is lonely.
So he sold his soul to the Devil in exchange for "a friend or two." He got what he wanted in the form of two extra heads.
  • Perhaps he was an outcast due to the stutter he has. Or maybe people were afraid of him.
  • Maybe he was an outcast from the other dragons for not having horns since the baby dragons in "Rugged Ridge" have horns, but Grimm doesn't.
  • When making the deal with the Devil, he may have said for two friends "To keep me company on a rainy day", meaning figuratively, when he's sad and lonely. However, the Devil took it literally (probably on purpose) so that he only gets his friends when it's raining. That's why the extra heads don't appear in the battle until it starts raining.

Werner Werman is in a war against the cats.
He sold his soul to swing the battle in his favor. That's why he has his cat Mecha; to infiltrate the cat army and destroy them from the inside.

Alternatively, Werner Werman is in a war against other rats, and has allied himself with the cats.
This is supported by the fact that the cat mecha has ghost rats/mice inside it. Werner is actually a Boomerang Bigot who actually wanted to be a cat or believes in their supremacy, which is why he was granted a mecha that would allow him to fit within cat society.
  • A possible alternate explanation: He really does want to beat the cats, but the Devil — being a Jackass Genie — gave him a mecha that was not just Powered by a Forsaken Child but by the souls of comrades killed by the cats.
    • Another alternate explanation: The ghosts are just holograms meant to convince the cats that he's one of them. This is supported by how they seem to glitch and phase out when defeated.

Reasons for bosses selling their souls to the Devil.
Wanting superpowers aside, it might be possible to deduct what each boss wanted from the Devil in exchange for their souls by looking at their quotes, powers, and transformations.
  • The Root Pack: Once regular-sized vegetables, they became huge in order to avoid being harvested and eaten.
    • It's also likely Psycarrot also asked for psychic abilities as well, which might explain why he seems more unhinged than the other two.
  • Goopy le Grande: Probably wanted to become a big and strong boxer, thus he obtained steroid-like pills from the Devil. Supported by his surname "Grande" meaning "big" in Portuguese/Spanish/Italian and both his first and second phases using boxing moves.
    • Alternatively, a second lease on life. Hence why his tombstone is alive and still acts like it's him.
  • Hilda Berg: Probably wanted to fly around, so she became a blimp (either intentionally or because the Devil was being the Jackass Genie he is). Notice that her blimp body is not her original form.
  • Cagney Carnation: Take Over the World (supported by second Game Over quote).
    • Or he could have just wanted to be more intimidating, so he wouldn't get trampled/picked/otherwise abused as flowers often are.
  • Ribby and Croaks: Wanted to become strong fighters. They mention being born with a fighting soul, but in truth were actually quite wimpy (supported by their Simple Mode knockout animation)
    • They might have phrased that wish as "to be the strongest fighters around," which the Devil chose to interpret as just surrounding them with creatures weaker than them, hence the fly nightclub.
    • Alternatively, they wanted access to the riverboat club so that they could eat the flies. Thus, the Devil gave them the ability to transform into a slot machine, something no one would bat an eye at in that setting.
  • Baroness von Bon Bon: Her very own Sugar Bowl, complete with sweets as lackeys. What else?
  • Djimmi the Great: Freedom from genie duty, so he's free to just use his magic as he wants.
  • Wally Warbles: Freedom to fly wherever he wanted, so he was made stronger than any bird, like the eagles he mentions. He might also wanted strength to protect his son.
    • Alternatively, he wanted children, which is why he has a son and eggs, but no mate in sight.
  • Beppi the Clown: He wanted to create his own amusement park, which is why he can summon and turn into the attractions themselves.
  • Grim Matchstick: He was lonely. See the entry above.
  • Rumor Honeybottoms: She really needed that much honey, which is why she's so protective of it.
    • Alternatively, she might have asked for that magic book and wand she carries.
  • Cala Maria: She liked attention (as seen by her introduction), so she was made enormous to the point no one would miss her.
    • Well, she is down to near-human size in the good ending...
    • Or if her gorgon form is her true form, she could have wished to be beautiful.
    • Taking influence from the cartoon, she sold her soul to become the most feared monster in the seven seas, with the Devil giving her the ability to transform into her gorgon form to accomplish that.
  • Captain Brineybeard: Most likely money to afford his own ship and/or to give sentience to the ship. Or he traded his soul for the ship itself.
  • Phantom Express: Probably was out of service for whatever reason, so it wished to be repaired and reclaim its job. It's also possible that the blind ghost, the skeleton conductor, and the living chairs were all involved in bringing back the train, otherwise they would have nowhere else to work.
    • Alternatively, they could have been the Devil’s old method of transporting souls down to Inkwell Hell, given how their tunnel goes into the same mountain range the casino’s in. There could have been a disagreement leading to the train staff getting fired and the Devil wants their souls as payment.
    • It could be the Devil also just wants whatever souls happen to be aboard and the Phantom Express never made any deal with him or lost any gambles. Old Scratch hadn’t been able to directly take the souls so he thought the Cups would be up to the job instead.
  • Sally Stageplay: Fame and Fortune. Obviously.
  • Werner Werman: Power to beat the cats. Thus a cat mecha (see entry above).
  • Dr. Kahl's Robot: Probably a failed experiment of Kahl that wished to become an effective destruction machine, so its creator could appreciate it.
    • Maybe it's the gems, instead. Those things seem WAYYYY too powerful to be NORMAL gemstones...
    • Also a possible indication that Dr. Kahl himself is smarter than he lets on, by tricking the Devil into taking the robot's soul instead of his own. Of course, the Devil comes to collect anyway, if only to save face.
    • Or the deal could have been how he gained a soul in the first place (on a lease, of course).
  • I assumed that they all simply gambled their souls away, like our protagonists. A boring answer, I know, but some of them still have gambling themes such as Ribby and Croaks, so it would've made sense for them to gamble.
    • That actually makes sense. Chip (the axe guy) does say he was trying to fight off "casino debtors". My guess is that some of the bosses (like most of the first Isle bosses minus Hilda Berg) gambled their souls why, whilst others made special deals.

On that note — the bosses' personalities when they're not bargaining/fighting for their immortal souls...
  • The Root Pack: basically The Three Stooges as vegetables (in fact, Moe Tato's name might be an unconscious Shout-Out). Per classic Comic Trio conventions, Psycarrot's the leader, Weepy's the complainer, Moe Tato's the dingbat. Heck, their Deal with the Devil might've even begun as a get-rich-quick scheme.
  • Rumor Honeybottoms: a strict, penny-pinching, but mostly Honest Corporate Executive. May disdain males, as most of her staff (except her head of security) consists of female workers like in real-life beehives.
    • Seems unlikely that she Does Not Like Men given all of her staff appear to actually be male. Maybe she's a bit of an oddball for the fact that she specifically hires male bees, though their miserable appearance may imply she's still a bit of a stickler for making sure things get done thus really rough work days.
  • Captain Brineybeard: actually terrified of the open sea and has never sailed more than half a mile or so from the isles. Mostly spends his time hanging out at harbor pubs, telling loud, boastful stories to anyone who will listen.
  • Baroness von Bon Bon: a bratty circus performer who juggled her many detachable heads. She has a powerful sweet tooth that is exploited by others to no end.
  • Cala Maria: A shameless flirt (or beyond), who is generally something of an Attention Whore. Possible on-again-off-again relationship with Brineybeard (either platonic, romantic, or alternating between them), due to their shared motifs and close proximity to each other.

Sally Stageplay is Darla Dimple's mother.
Just something I thought of the other day.
  • Both characters are blonde, but that's about the only genetic similarity between the two.

Between his defeat and the end of the game, Wally was in hell.
Wally is presumed to be killed after his boss fights by being eaten by his hench-birds. Should you reach the good ending, Cuphead and Mugman burning the contracts automatically frees him from being trapped in hell for all eternity.

What happened to the missing bosses.
Theories on what possibly happened to the bosses that do not appear in the epilogue.
  • The Root Pack: They were permanently dead briefly, but once the boys managed to free their souls from the Devil, the Root Pack's souls merely transferred into new, non-toon vegetables. The reason they do not join the party is because their new bodies are still too young and have some growing up to do.
    • If they didn't die upon defeat, perhaps they didn't show up because, being vegetables, they're immobile and unable to leave their garden.
  • Goopy le Grande: Killed Off for Real. His abuse of steroids he most likely obtained from the Devil finally did him in, his fight against the boys being what actually killed him. The destruction of his tombstone made sure that he would not come back to life when his soul contract was destroyed.
  • Wally Warbles: The medic birds, most likely sent by the Devil, that carried his stretcher went through with eating him alive during his last moments, preventing him from being resurrected. Wally's son, meanwhile, is too busy grieving his father's death to join in celebrating the Devil's defeat.
    • If he didn't die, he's probably still badly injured and possibly still resentful of the brothers, which is why he didn't show up.
  • Phantom Express: The ghost in the first phase was the one who made the deal with the Devil in the first place, damning the entire express to send the recently deceased to become patrons to the Devil's casino instead of to the afterlife, which was its original job. The reason the rest of the train attacked after the first phase was basically it and the conductor acting in self-defense against agents coming to collect. After the Express's contract is destroyed, it left the first phase ghost in the realm to the living, forever denied a chance to finally move on......which was exactly what that ghost wanted in the first place.
  • Dr. Kahl: Since it was his creation that sold its soul to the Devil after the boys defeated him, Kahl immediately went back to the drawing board in order to figure out how his robot, originally made to be a lifeless war machine, gained enough sentience to actually sell his soul in the first place — and, for that matter, gained a soul. Kahl doesn't join in the celebration because he both felt that he was never really involved with the whole soul contract plot in the first place, and he was busy with his research.
  • They were all actually present at the scene. Just offscreen so that the crew can avoid drawing them all in a single page/panel (is my theory).

The bosses were conspiring in some way.
  • That's why they all had the same plan to welch on the Devil and beat up anyone who tried to stop them. All the bosses are part of a group of Inkwell Isle residents who had been meeting in secret to try and figure out what to do about the Devil coming for their souls, and that was the solution they agreed on.

Combining the above two...
  • Some time before the events of the game, several (maybe even all) of the bosses assembled into a Caper Crew and stole their contracts out of the Devil's office. This will be the plot of the next game, which will feature many new denizens of Inkwell Hell as bosses. Cuphead and Mugman only ran into so (relatively) few of them because the rest were recovering from the beating the Crew gave them or got (hell)fired by the Devil for letting the theft happen.

The actor playing Sally's husband wasn't her actual husband, but they did actually fall in love between the boss fight with her and the game's ending.
  • Possibly from him comforting her backstage after she got publicly humiliated and lost her soul.

Rumor Honeybottoms is a defense contractor.
  • That spellbook she flips through isn't a spellbook - it's a company catalog. Only her wand was provided by the Devil.

Wally Warbles' Finger Gun attack? It was originally an, ah, different gesture.
  • Self-explanatory, really. Even if the devs never seriously considered this, I daresay the attack began as this at the sketch/conceptual level.

What the boys pour into their heads for each attack.
  • Expanding on that entry in the Headscratchers page...
    • Peashooter: Pea soup, as suggested on the Headscratchers page.
    • Spread: Red Bull, or whatever the Inkwell Isle equivalent is. Packs the biggest punch, but can't go all that far.
    • Chaser: Fruit juice or some soft drink. Weak but can be downed like water, and great as a chaser for stronger stuff.
    • Roundabout: Absinthe, or any other booze that tastes mild at first but comes back with a vengeance when the drinker foolishly downs more.
    • Charge: Possibly hot sauce, due to the fiery visuals.
    • Lobber: Grape juice, wine, or any other drink made from grapes. It's purple in color and oval in shape.

Werner Werman is fighting in Inkwell Isle's equivalent to World War I or World War II.
  • Not only were German soldiers called Jerrys, which would match up with Werman's German theme and share the name of the Mouse from Tom and Jerry, British soldiers were called Tommies which would again line up with Tom and Jerry. If we go on the above theory where Werner is in a war against the cats, it would make sense that the British Cats and German Rats would be fighting against each other because with the time period of the 30s, both World Wars happened somewhere around then.
    • The British flag hanging from the roof of Werner's home could be a prize he stole from them as well.

Elder Kettle has Medium Awareness.
  • At the end of the cutscene before entering Inkwell Isle Two, it looks very much like he's looking straight at the player. When he's saying to "do the right thing", perhaps he's not talking to Cuphead and Mugman. He knows that his boys are good, despite their tendency to get in trouble - it's you he's worried about. Maybe he's well aware of Video Game Cruelty Potential, and wants to convince you not to do it.

The next game will go into more detail on Elder Kettle.
We don't necessarily need a prequel game that's all about him, but it would be nice if they would at least explain how he is related to Cuphead and Mugman. For example, if he's actually their foster parent, maybe the game would tell us the story of how he adopted them. Some more info on the Legendary Chalice would be nice too...
  • Well, the DLC will feature Chalice as a playable character, and does flesh her out, so maybe...

Elder Kettle is a benevolent version of The Chessmaster.
"Benevolent" is a keyword here. He is by no means a bad person, and he certainly didn't want the Devil to take Cuphead and Mugman's souls. He would have preferred it if Cuphead and Mugman obeyed him and stayed close to homenote , but if they didn't, he was ready. He had the potion right with him so that if Cuphead and Mugman got themselves in trouble with the Devil, he could send them on the path to fixing their mistakes. He was aware of the Devil's greed, so he came up with a plan to have Cuphead and Mugman take advantage of this and finally give the Devil what he had coming. However, it was also a test to see if Cuphead and Mugman were responsible enough to save the isle on their own. Kettle likely would have stepped in if they really needed him to, but they beat every enemy on their own, and in the Good Ending, they passed the test with flying colors. No wonder Kettle was brimming with pride.

King Dice is an Evil Counterpart.
King Dice, as he explains in his theme song, never plays nice. His good counterpart is King Nice, who never plays dice.
  • King Nice, of course, is the Lord God's right hand man. And he wants you to get rid of those contracts.
  • Not to mention, he’s the last game in the land.
  • What about the benevolent King of Games?

Cuphead is part of a Shared Universe with Enchanted Portals.
Just take a look at the trailer
  • Considering Enchanted Portals travels its heroes to many worlds, they could travel to Inkwell.

Plots of the cartoons the bosses originated from.
  • Botanic Panic: A garden of sentient vegetables tries to avoid being picked and eaten.
  • Ruse of an Ooze: A Blob Monster cheats his way through a boxing tournament by shapeshifting, taking pills to grow larger, and even faking his own death.
  • Threatenin’ Zeppelin: An aviator is terrorized by a troublesome blimp-witch after they “trespass” in her airspace.
  • Clip Joint Calamity: A bumbling frog duo (Possibly expies of Abbott and Costello or George and Lennie) try (and fail) various methods of sneaking into a riverboat club run by flies to eat the patrons.
  • Floral Fury: In a society of sentient plants, a group of policemen tries to thwart and discover the identity of the mysterious leader of a group of flower gangsters, who turns out to have been a Devil in Plain Sight.
  • Sugarland Shimmy: The rulers of Sugarland suddenly fall ill, leaving their bratty daughter in charge. Her group of evil advisors try to manipulate her, but she refuses to listen to them, instead making their lives miserable. Eventually, they find her so insufferable that they turn themselves in and provide the antidote to the poison they slipped the former rulers.
  • Carnival Kerfuffle: A curious clown causes various mischief at the carnival where he works while trying to avoid being fired by his no-nonsense boss.
  • Pyramid Peril: A grave robber discovers a lamp containing a Jackass Genie. He takes it, thinking all his problems are over, but the genie constantly gets him in trouble and chooses the worst possible interpretations of his wishes. Eventually, he gets so frustrated that he sneaks it back into the pyramid, and all’s well that ends well. At least, until another grave robber finds it at the end...
  • Aviary Action: A giant bird with a Hair-Trigger Temper struggles to raise his troublemaking Insufferable Genius son.
  • Fiery Frolic: A knight tries to rescue a princess from a lonely dragon who kidnaps her for some company.
  • Honeycomb Herald: A look inside the offices of a newspaper run by a hive of bees.
  • Shootin' n’ Lootin: A pirate visits a kingdom of sea creatures and ends up taming a whale, which he then uses as a ship. Has a Framing Device of pirates swapping stories at a bar.
  • Murine Corps: A group of militaristic mice sneak into a house through the use of a Trojan Cat and proceed to wreak havoc on the homeowners.
  • Junkyard Jive: A mad scientist creates a robot from scrap to Take Over the World, but he finds the robot is only interested in being an entertainer.
  • High Seas Hi-Jinx: A group of sailors try to escape from the giant Attention Whore mermaid who has wrecked their ship for a Captive Audience.
  • Dramatic Fanatic: A play is being put on, but behind the scenes, things keep going wrong and everyone is scrambling to keep the audience from finding out.
  • Railroad Wrath: A criminal trying to escape the police accidentally stows away on an Afterlife Express, upon which the various ghosts and ghouls torment him before dragging him off to the Land of the Dead with them.
  • All Bets Are Off: Various gambling implements in a casino come to life and get up to musical mischief, in the vein of Have You Got Any Castles? or Book Revue. Featuring a rotoscoped song and dance from King Dice.
  • One Hell Of A Time: A peek into perdition as the Devil judges various sinners and sends them off to their appropriate, often comedic punishments.
  • The Run-and-Gun Levels cartoons:
    • Forest Follies:
    • Treetop Trouble:
    • Funfair Fever:
    • Funhouse Frazzle:
    • Perilous Pears:
    • Rugged Ridge:
  • The DLC Bosses cartoons:
    • Gnome Way Out: A merry band of gnomes discover a mountain cave rich with gold, however, when they begin to mine it, it gives a toothache to the sleeping giant that mountain is in reality, and he wakes up, swallowing them whole. The rest of the cartoon is the gnomes exploring the giant’s inner workings attempting to find a way out before a short battle between them and him once they escape.
    • Snow Cult Scuffle: A traveler wandering through a snowstorm comes across a building made of ice. They try to enter for some shelter, but are locked out, with a sign saying “MEMBERS ONLY”. They eventually sneak in by picking away at the walls but stumble upon the secret proceedings of a blizzard wizard and his loyal legion of animate snowmen, who spot the traveler and chase them around.
    • High-Noon Hoopla: A corrupt cowgirl travels in her mobile saloon to a down-on-its-luck town, claiming to be a sheriff, and scams everyone out of their valuables before they revolt and make her into sausages.
    • Doggone Dogfight: A literal dogfight between a bulldog pilot and another canine flying ace. When the bulldog finds out his opponent is female, he falls madly in love with her, and a Flash Forward at the end shows them with four jet-powered pups.
    • Bootlegger Boogie: Ant cops get a tip-off and raid a bug speakeasy. They dispose of the spider gangster running it, his fly flunkies, an insectoid singer, and a drunken caterpillar who got roped in, only to be taken out by The Man in Front of the Man: The snail MC, who rides in on an anteater.
    • A Dish To Die For: A Hansel and Gretel type story where a cook invites the protagonists, which are sentient food, into his kitchen with the promise of food and then tries to bake them into sweets.
    • The King's Leap: A child falls asleep playing chess and dreams of a chess kingdom where the king is holding a tournament. They make their way through, but then have to fight the Queen, who has been betting against them. Upon defeating her, they are crowned the new ruler of the chess kingdom and wake up.

The reason Wally Warbles is fought on Isle 2 is because he was taking his son to see the carnival.

Baroness Von Bon Bon isn't really a Baroness
That's just her stage name. Really she is a performer of some kind for the carnival. Although what she does... I don't know. Maybe someone else has an idea.

The final phases of the debtors are coursed by the Devil or King Dice's intervention
All the debtors have two difficulty settings, simple and regular. Simple is when the debtors are left to fight Cuphead at their own devices, whilst regular is when either the Devil or King Dice intervenes to make things harder.
  • Root Pack: The exception. instead of gaining a final phase, Ollie is sent against his will to fight Cuphead. If you don't attack him, he will leave and be replaced by the radish.
  • Goopy: defeated in his second phase, but the Devil/King Dice summons a tombstone to keep on fighting.
  • Hilda: Is given the power to turn into her moon, spaceship form.
  • Cagney: Is given some extra growth to turn into his super form.
  • Ribby and Croaks: Are merged together as a slot machine. I imagine King Dice may have been behind this.
  • Baroness Von Bon Bon: Was planning on using her shot-gun after her third minion (which she does in simple mode), but instead get's the idea to use it during the fight with the third minion, she also gains the power to regrow her heads and make her castle attack.
  • Djimmi: Given extra power for a fifth phase.
  • Beppi: After he falls off his horse, he's transformed into his chair swing form.
  • Grim Matchstick: The Devil/King Dice makes it rain. (if you read the "Grim Matchstick is Lonely" WMG above, you will see I suggested he can only grow extra heads in the rain.
  • Wally: Has paramedic birds sent to get him so he can keep fighting a bit longer. (if they were sent by the Devil, that might explain why they are cannibals)
  • Honeybottoms: Is given her spellbook to tell her how to turn into a plane.
  • Brineybeard: His ship is transformed into a monster.
  • Cala Maria: The devil/King Dice does something to keep her head alive even after her body is destroyed.
  • Dr. Kahl's robot: Convinces Dr. Kahl to use his secret weapon, the jewel, to fight Cuphead.
  • They get the audience excited enough for Sally to appear for an ovation. They may also have tampered with the scenery so that the (cardboard)chandelier will fall on Sally's husband and "kill" him.
  • Werner: They activate his cat robot to help Werner fight.
  • Phantom Express: Does something to the train to make it attack.
This could explain why you can't get the contracts in simple mode. The bosses aren't just going to hand their souls over to a couple of kids claiming to be sent by the Devil. Off course, if the Devil or King Dice were present, then that would be different.

Simple Mode is not a fight to the death, just a sparring match
The bosses hold back enough to skip phases, and you get no soul contract if you beat them.

The other bosses will get secret phases (slowly but surely)
Do you know how in the Switch version of the game, The Root Pack, Djimmi, and Sally Stageplay got secret phases? Well, the other bosses will get secret phases as well (1-3 at a time of course) But what should they be?
  • Goopy Le Grande: His scrapped Indigo twin will appear (don't know how he could be unlocked, but whatever)
  • King Dice: If you land on Start Over, and somehow land on Start Over AGAIN, it will send you to the scrapped Pachinko mini-boss

The entire game takes place in something akin to a Dark World from Delta Rune.
Given the number of obviously object-based bosses in the game, I'm surprised nobody's said this yet.What each character is in the Light World would be as follows:
  • Cuphead is a cup, Mugman is a mug, and the Elder Kettle is a kettle.
  • The Root Pack is a bunch of vegetables in the garden, obviously. Probably prize winners from a fair.
  • Goopy le Grande is a blueberry that rotted and got all mushy.
  • Hilda Berg is a wind rotate thing on the roof (weathercock). Alternatively, she may be a Lightner human.
  • Cagney Carnation is a flower.
  • Ribby and Croaks are two Lightner frogs.
  • Baroness von Bon Bon's castle is a birthday cake in the sweets drawer of the pantry. She herself is a Lightner humanoid, and her minions are tins used to store candy and flour in the case of the waffle.
  • Calix Animi/Ms. Chalice is a broken chalice whose pieces were scattered around the house. The Mausoleums are the drawers her pieces were put into.
  • Beppi and his horses are balloon animals put up for the homeowner's birthday.
  • Grim Matchstick is a blowtorch. Alternatively, he may be a Lightner dragon, with his extra heads perhaps being the blowtorches he owns.
  • Wally Warbles is a cuckoo clock. His son is a smaller cuckoo clock.
  • Werner Werman is a Lightner mouse, and the cat animatronic he gets captured by is a cat-ears headband with a metal reinforcing piece inside, most likely his own.
  • The Phantom Express is a toy train set that got boxed in with Halloween decorations when the homeowner moved houses and didn't get taken out.
  • Chips Bettigan is a stack of poker chips, whereas Hopus Pocus is one of the cards from a poker deck (most likely the jack. Pip and Dot are dominoes, Mangosteen is the 8-ball from a pool table, Mr. Chimes is a cymbal monkey toy that was won from an arcade claw machine (and it still has the tag on the back of its head), Pirouletta is a roulette wheel, Mr. Wheezy is a cigar, the Tipsy Troop is the contents of the liquor drawer, Phear Lap is a mechanical horse-racer machine, and King Dice is a die. These are all fairly obvious choices.
  • The Devil is a fur coat.

Elder Kettle is the boy's biological father
  • Why is he elderly? He was experiencing a mid-life crisis and went on a night on the town, he met some lady, one thing led to another, and out came Cuphead and Mugman.

Doctor Kahl's Robot didn't have a soul at first
  • Based on a youtube comment I saw. It's a sorta Pinnochio kinda deal; Kahl wanted his robot to have true life, so he went to the Devil to ask him to give his robot a soul. The Devil obliged... and gave the robot a soul bound by a contract. That's why the contract is for the robot and not the doctor himself: the Devil is claiming him as his property! No wonder Kahl stole the contract and ran off!

King Dice is Authority in Name Only, and not actual nobility.
Maybe "King" Dice is just a stage name. He seems like just a normal casino manager, aside from the whole "Devil's right-hand man" thing. There's not much in the game to suggest that he's really a noble. And "The King's Court" could just be a metaphor.

    DLC Pre-release 
Chef Saltbaker will turn out to be evil, maybe even the Final Boss of the DLC.
He must be a very important character in the DLC's story, considering the prominent role he has in the announcement trailer. What if he's actually an Evil Chef?
  • Adding on to this, he's either one of The Devil's minions or even The Devil in disguise, seeking to take the souls of every inhabitant of Inkwell Isles.
  • A screenshot reveals a flag outside the bakery.
  • Seemingly Jossed by the July 2 trailer, which shows him getting along with Cuphead, Mugman, and Ms. Chalice quite nicely. Unless, of course, he's just a very convincing Hidden Villain.
  • Going with the Hidden Villain idea, Saltbaker will initially be friendly with the trio, but it'll be revealed that he was tricking them into helping with some evil scheme and once that's accomplished, he'll try to dispose of them.
  • Or, he really IS that friendly, and the main antagonist will be his rival, a living pepper shaker to contrast Chef Saltbaker being a living salt shaker.
  • Or he could be a reluctant villain who for whatever reason has no choice but to do the Devil's bidding.
  • CONFIRMED, though all of the above theories are Jossed in regards to the circumstances.

This update will add animation to the cutscenes.
While the animations we see in the trailer mostly seem like they won't actually be in-game cutscenes, they do have a certain style that would work great for cutscenes.
  • Jossed in the best way possible. Animated cutscenes were added in an update before the DLC.

This time, the protagonists are collecting ingredients from the bosses instead of soul contracts.
The goal is to gather ingredients to put together some sort of recipe (for a Delicious Last Course), but the bosses are holding onto them for some reason. Perhaps these bosses will be more clearly villainous than the Devil's debtors.
  • Confirmed! The official DLC soundtrack reveals that the Cup Trio must collect ingredients to bake the Wondertart, which will make Ms. Chalice real. As for the bosses being more villainous, the trailer seems to imply they are, but we'll have to wait and see.

The playable characters will be made more diversified in a Balance, Power, Skill, Gimmick sort of way.
We've already seen that Ms. Chalice can Double Jump, which is presumably going to be something exclusive to her alone. Maybe Cuphead and Mugman will have different "stats" in this update to balance things out.
  • Cuphead might be Balance, which is typical of main characters, or maybe Power because he's the Red Oni of the Red Oni, Blue Oni duo.
  • Mugman might be Strength if Balance goes to Cuphead, but he could be Balance because he's the Blue Oni.
  • Ms. Chalice will most certainly be Skill, based on that double jump.
  • There may not be a Gimmick-based character unless there's a secret 4th playable character we don't know about yet.
  • Jossed. Cuphead and Mugman still play exactly the same. Also, there is no fourth character.

There will be at least one boss rematch
Perhaps one of the bosses in the update will be a rematch against one of the original debtors, complete with new attacks and possibly phases. My personal idea is that one of the King's Court bosses will be refought, this time being much more fleshed out and having multiple phases.
  • Well my personal idea is Rumor Honeybottoms. Her honey could be one of the ingredients needed for the Wondertart, and her music is just that good
    • Semi-confirmed, as the nightmare battle could be considered a rematch of sorts with the Devil. Maybe.

The new DLC Inkwell Isle will be accessed through Rugged Ridge
If you pay attention to the latter part of this level, you can find statues and decorations of some sort of chalice royal family. Since the DLC is about Legendary Chalice, this level might have some sort of connection to her past.
  • Seemingly Jossed: In one of the trailers, we see the characters access the island by boat.
  • Jossed. The DLC adds a boat to each Isle (not counting Inkwell Hell) that will take you to Inkwell Isle IV, or to any other isle.

Some of the bosses that were originally cut from the game will be used here.
The Giant Spider would be a nice addition, for example.
  • The song used in the DLC reveal trailer is "The Airship" one of the cut songs from the game. This might be hinting at the return of some of the cut levels/Bosses
    • Confirmed, just not in the way anyone expected, the scrapped boss revived is The Light.
    • The spider is also revived but retrofitted as the first stage of the Moonshine Mob. And the replacement of The Light is the second phase of the same fight.
    • The Knight from King's Leap has some ideas from Jelly the Octopus too.

The acronym "DLC" will have a hidden double - or rather, triple meaning.
As some have pointed out, the DLC's tagline, "Delicious Last Course", uses the same acronym. What if there's another way that acronym will be used in this update? The base game has the Devil's Casino... maybe an L word will be added to that?
  • Lady Chalice will have an Evil Counterpart called Dark Lady Chalice
  • The Devil will have more than one casino, and the focus of the DLC is to take down the Devil's Last Casino.
  • Or perhaps Devil's Last Chance, as in his last chance to get Cuphead and Mugman's souls.
    • Or simply Devil's Latest Chance, as in his latest attempt to get Cuphead and Mugman
  • Jossed, there is no hidden triple meaning.

Legendary Chalice is Ms. Chalice's superpowered form.
Ms. Chalice is her true identity, and the mausoleum levels were tests for the brothers. With the new DLC, she has returned to her normal identity to join them in fighting whatever the new threat is.
  • Ms. Chalice's Super Art 3 has her temporarily transform into her Legendary Chalice form (as seen in Rugged Ridge) to call forth the Calix Animi and lay waste to her enemies, so there is some merit to this.

The story - or the closest thing to it this DLC has - will be much heavier on No Fourth Wall jokes.
Possibly to the point of confirming that all of Cuphead runs on an Animated Actors system, with no "real" stakes (except when convenient to the plot and/or humor, of course).
  • Jossed, there are no meta jokes in the story. The closest thing is the Interface Screw in the Howling Aces' boss fight, where the airship grabs the camera and rotates it.

Ms. Chalice cannot parry.
That's why she was given the Double Jump to balance things out. That also explains why, as the Legendary Chalice, she keeps getting captured by the ghosts - she can't perform the only move that can defeat them.
  • That or she CAN parry, and now Cuphead and Mugman can double jump too
    • Jossed... she can parry, but has to dash to do so. As she has to move too much, though, and the ghosts tend to come from everywhere, they can still overwhelm her more easily than the boys.

The Double Jump is a charm-based skill.

One of the bosses will be a Black Knight.
They will be actively pursuing Grim, simply for being a dragon, and the Cup Bros and Ms. Chalice will show up just in time to save him.
  • The release date trailer confirmed a knight-type boss, but that's all we know about them so far.
  • Jossed. The Knight, who was previously mentioned, has no interactions with Grim. The King's Leap bosses are implied to be just playing a game rather than actually trying to kill anyone, so it's unlikely that the Knight would truly be that evil.

There will be a boss based on the infamous cylinder from the tutorial.
  • Jossed; it would be too hard to beat, especially for journalists.

Alternatively for Ms. Chalice...
At some point, either Cuphead or Mugman parry-slapped her back into existence, reverting her to the age she was when she originally died.
  • Jossed, she comes back to life when Cuphead or Mugman eats an Astral Cookie, which causes them to briefly swap places with Ms. Chalice so that they're a ghost, and she is alive.

The Snowlem seen in one of the trailers is not the main boss of the level.
The battle seems to take place in an Ice Palace, complete with a throne in the background. As noted on the Cuphead Wiki, the Snowlem seems to be an escaped prisoner, judging by his broken handcuff. More likely, he is merely a minion you fight in (one of) the phase(s) leading up to the actual main boss, not unlike Baroness Von Bon Bon's court members or Rumor Honeybottoms's police bee. The actual main boss is probably either a Winter Royal Lady (possibly based on The Snow Queen) or Jack Frost.
  • Confirmed, although the main boss appears to be some sort of wizard.
    • Actually Jossed... kinda... The Snowlem is one of the wizard's forms

Ingredients that the new bosses will possess.
  • With the confirmation that Cuphead and Co. are collecting ingredients to make a Wondertart, it's not unreasonable to assume that the new bosses will each be carrying an ingredient unique to them that the player will see upon defeating them for the first time. Possible ingredients and why the bosses have them include:
    • Glumstone- Bread, because he's a giant, and giants like to grind people's bones to make their bread.
      • Jossed. The ingredient you get is Gnome Berries.
    • Winter Wizard- Either icing or frosting to go on the Wondertart. Self-explanatory. Maybe even ice cream, but not likely.
      • Jossed. Snow Sugar is Mortimer's ingredient.
    • Sheriff Winchester- Milk, because she's a cow.
      • Jossed. Desert Limes is what the cups get from her fight.
    • Horse Knight- Either butter or eggs, since those were commonly produced on farms during Medival times.
      • Jossed. Turns out the chess pieces are simply an extra challenge to earn more coins.
    • Bulldogs- Probably some kind of whisky or something given how often soldiers drank. Or maybe the bros need Canteen to fly them to one of the ingredients and the bulldogs are in the way.
      • Jossed. The dogfight gives you Pineapple Mint.

At least some of the debtors will show up as NPCs
Likely allies to the Cup Trio.
  • Confirmed! In an Easter Egg, spinning in place can summon Game Djimmi, who will grant the cups extra health for their next battle.

The Final Boss will be the third member of a Terrible Trio with the Devil and King Dice
Whoever they are, they had their own reasons for not showing up in the main game, though they may have been the ones who won the bet with King Dice. Possibly a female villain as Ms. Chalice's Evil Counterpart.
  • Jossed. As evil as he is, there's no implication that Chef Saltbaker is allied with the Devil.

Either the Final Boss or the Pre-Final Boss will be Ms. Chalice herself
If the WMG above about Saltbaker being a villain turns out to be true, the "Wondertart" will end up corrupting Ms. Chalice, leading to Cuphead and Mugman having an "I Know You're in There Somewhere" Fight against her. And yes, this would mean no double jump during this battle.
  • Jossed. Although Saltbaker is evil, he doesn't turn Ms. Chalice against you; instead, he simply fights you himself.

The Chess Knight is working for King Dice
They're both related to board games, so there could be a connection between the two.
  • Jossed. The Knight is one of five optional chess piece battles as part of the King’s challenge.

Chef Saltbaker is the Devil's Arch-Enemy
After all, salt is commonly depicted as a repellent against demons.

The bosses are mercenaries hired by the Final Boss/Big Bad of the DLC
If Saltbaker is the Big Bad, it would explain how all the bosses conveniently happen to have the ingredients needed to make the Wondertart.
  • Jossed. They're guarding the ingredients for the Wondertart, which is why Saltbaker needs Cuphead and Mugman to get the ingredients from them.

The scrapped Airship level will finally be playable in the DLC
We heard the Airship level theme in the DLC's initial announcement trailer, plus, so far the new isle only has 4 bosses, whereas the other isles, (besides Inkwell Hell) have 5-6 bosses
  • The ingredient they possess is rainbow sprinkles
  • That, or they might even be the main villains of the Delicious Last Course. At the end of the Game Show Awards trailer, our heroes left the isle via airplane
  • In IGN's "Worth the Wait?" video, we see some sort of ladder going into the sky on the world map...
    • Jossed, unfortunately. It's replaced by King's Leap.

At least one more scrapped boss will be revived for the DLC
Either the Spider or the Bat Demon thing
  • The ingredient either of them has is the magic needed for the Wondertart to be magical
  • Confirmed. The spider is back, and instead of a flying battle, he’s one of the mobsters fought during Bootlegger Boogie. The “light” boss is also brought back as the very next phase, as a dancing Light Bug playing music.

The Calix Animi will be given more backstory.
In the Rugged Ridge level, we find the ruins of the headquarters for an ancient order of heroes including a statue of the Legendary Chalice when she was alive. We may see more pieces of their history in the background on this new island.
  • Given Chef Saltbaker’s affinity for magical recipes, it’s possible he was the cook for the Calix Animi. Powering up his Allies with magical baked goods to give them more of an edge.
  • Kinda confirmed? It's obviously not the main focus or anything, but in Ms. Chalice's third super art, she turns into the form she was depicted as in her statue and launches an army of what can only be her fellow Calix Animi soldiers.

That spin laser Ms. Chalice pulled in the Nintendo Direct trailer was actually the first Super Art
Meaning in the DLC you can use the first Super Art vertically.
  • Technically confirmed, but you can't use it vertically, it's just how Ms. Chalice uses it.

Ms. Chalice's second Super Art will be her initial form
Do you know how the second Super Art is when you can summon ghosts to help beat up the boss? Well for Ms. Chalice, her ghost will be her initial mausoleum form.
  • Jossed: It's technically her third super art, and she doesn't transform into her ghost form, but rather her full form.

You need to complete the DLC Isle in order to play as Ms. Chalice in the main isles
  • Jossed. Once you watch the intro cutscene for the DLC, you can use the Astral Cookie charm, and therefore Ms. Chalice, anywhere.

Possible Ideas for other Bosses
Glumstone the Giant, Snow Wizard, Sheriff Winchester, and Horse Knight are the only four bosses that were confirmed to appear as bosses in The Delicious Last Course. There are some other possibilities of what the other bosses might look like.
  • Fighting a giant ape in a jungle with references to King Kong and Donkey Kong
  • An underwater battle with a shark.
  • A battle in an ancient tomb with an awoken mummy.
  • An alien encounter with a ufo(not the ones Hilda send out).
  • A battle on a ship against a sailor a la Popeye
    • All jossed.

Ms. Chalice will betray Cuphead and Mugman.
  • Ms. Chalice is on a *secret mission* from Chef Saltbaker, who seems like a candidate for twist villain. Ms. Chalice is easier to play than Cuphead and Mugman. In the base game, you couldn't beat the final boss by using simple mode...
  • Jossed. It’s not Ms. Chalice who turns traitor…

One of Sheriff Winchester's phases will be a Shout-Out to Quick Draw McGraw.
  • Specifically, she will dress up as an Expy of Quick Draw's alter ego, El Kabong, likely as her final phase.
    • Jossed.
    • In one phase, Esther takes a ride in what looks like a saloon on wheels, and for another, she’s turned into what looks like sausage before resuming the fight. For her final phase, she’s crammed inside a tin of sausages.

Run and Gun levels?
Run and Gun levels have been featured in all the isles (Other than Inkwell Hell), so where are the ones here?
  • Jossed, there are no Run and Gun levels

Completing all levels on the island will unlock one final boss.
  • Possibly a rematch with the Devil or an entirely new villain from the Astral Plane.
  • The final level could take place on the Astral Plane.
  • Maybe Chef Saltbaker if he turns out to be evil
  • Relating to an above WMG, Ms. Chalice?!
  • The Scrapped Airship level?!
    • The Chef Saltbaker one is confirmed.
    • There is a fight in the Astral Plane, but it's an Optional Boss that doesn't require you to beat all the other levels.

    DLC Post-release 
The secret nightmare battle takes place on the Astral Plane.
  • The ghost detective does mention that there is heavy astral energy around the graveyard.

The secret nightmare battle is part of the Cursed Relic's test.
  • In order to even activate the secret boss you have to have the Broken Relic with you. The trial of the Cursed Relic is only meant for the best and should they fail, their soul is lost.
  • The angel and devil could also be the astral guardians of the relic waiting for a worthy hero to wield it.

The Howling Aces are a rival team of aviators to Canteen.
  • It would explain why Canteen came all the way to DLC Island to help against them.

Ms. Chalice is Cuphead and Mugman's mother
  • She is also the Elder Kettle's daughter, making the Elder Kettle the two boys' grandfather.

The final phases of each DLC Island boss fight are key to nabbing the Wondertart ingredients

  • Similar to the base game final phase WMG above, this would explain why Simple Mode does not grant the ingredient.
    • Glumstone already ate the Gnome Berries, and the only way to get them is to go into his stomach.
      • Alternatively, he needs to be properly subdued before the Gnome Berries become accessible. By only defeating the puppets, Glumstone is technically still left standing, and, being a giant, he would be perfectly capable of defending the berries even after defeat. On the other hand, giving him a stomachache would render him unwell enough to either agree to hand over the berries or become unable to guard them anymore. Or, his sentient stomach ulcer is a problem for him, and defeating it makes Glumstone feel better, leading to him gladly rewarding the berries as a token of gratitude.
    • The snail boss of the Moonshine Mob is the only one who knows where the Distillery Dough is, or how to prepare it.
      • Alternatively, the Anteater was the one guarding the Dough. Knocking him out meant there was nothing in the heroes' way to get the Dough, the boss notwithstanding.
    • The Pineapple Mint is kept inside the warship, which would explain why the secret final phase has the pups throwing pineapple grenades.
    • The Sugar Ice Cubes are made from the chipped remains of Mortimer Freeze's snowflake form.
    • Desert Limes are the secret ingredient of Prairie Dogs beef sausages.

Some bosses ate super mushrooms before their boss fights. The ones Chef Saltbacker eats before his second phase.
Esther Winchester is shown to be human-sized in the epilogue, yet is a giant in her boss battle. The Anteater is unusually massive, considering the bugs are all human-sized. The Chess Queen could be using mushrooms, or she could just be a size shifter. Chef Saltbaker starts the fight being giant-sized. Maybe he ate a shroom before the boss fight, then ate another before his second phase.

The reason most people don't use them is either because they are so rare, or the effects only work on certain people.

Chef Saltbaker used to work for the Devil
In his post-Heel–Face Turn song, Saltbaker sings "It's better to bake in heaven than to cook in hell". While this lyric is referring to his newfound realization that it's better to be good than evil, it could also have a Double Meaning about how he used to literally cook in Inkwell Hell as the Devil's personal chef, or simply the chef for the casino, which would be fitting since he was an Evil Chef.
  • This could explain why the first phase of his boss battle is similar to King Dice's. Both bosses are huge and in giant-sized versions of their places of work and attack with objects related to their jobs.

King Dice was redeemed off-screen
As bad as King Dice was, (at least from what we've seen of him) he's still nowhere near as bad as Chef Saltbaker. So with Saltbaker doing a Heel–Face Turn, who's to say King Dice couldn't do the same?

The King of Games is God's right hand man
He is the Good Counterpart of King Dice, he has a castle in the clouds and one of his champions is literally a Bishop. Whilst it might seem strange having an executioner as a champion at first, it makes sense when remember that executions were often done in God's name.
  • The Rook, being an executioner, could represent the angel of death, who is very much under God's control, as seen in the Book of Exodus.
  • The King of Games speaks in Old English, kind of like the King James Version of the Bible. (King James, King of Games... almost a perfect rhyme.)
  • The King of Games is introduced with an uplifting choir song that sounds a bit like a hymn. (The "la-la-la-la" music that comes after it is less hymnlike, but it does sound a bit like a Christmas carol, perhaps.)
  • God is sometimes referred to as the "King of Kings," so it would make sense for His right-hand man to be a literal, traditional king. (This is assuming that King Dice is Authority in Name Only. Although he leads the casino, there's not much to suggest that he is actual nobility.)

The angel in the hidden boss stage represents the Devil before his fall
In religion, the Devil was one of God's angels who was cast down into hell for rebelling against God. Who's to say that didn't happen in Cuphead's universe?

The Angel and Demon are literally the Devil's shoulder angel and demon
The Demon is always in front of you because the Devil obviously likes to show off his evil side, and the Angel is always behind you because the Devil has a good side that he hides from everyone.

One of the pink ghosts from the Mausoleums was used for the Wondertart that revived Ms. Chalice in the epilogue

The Astral Cookie is made out of Distillery Dough
The Astral Cookie could be seen as a primitive version of the Wondertart. The Moonshine Mob may have been selling it illegally to Chef Saltbaker. But since the Mob was in the middle of being raided by police, they couldn't sell it to the Chef and so the heroes needed to get it
  • Then why did they attack them also?
    • They assumed the heroes were trying to steal the dough for themselves. Remember, the Mob couldn't sell it whilst the police were raiding the place. Even crooks don't like having their merch robbed. Either that, or they thought they were cops.

Glumstone is a King Dice x The Devil shipper
Why does he have matching hand-puppets of King Dice and The Devil? He's also shown to be able to do tricks with the puppets effortlessly, implying he's played with them a lot before.
  • Well, during that phase, Glumstone's gnomes watch with glee, implying it isn't the first time he's put on a puppet show for a live audience. And considering how big he is, his puppets are the size of actual actors.

Names for the as-yet unnamed characters
These will probably all be Jossed in the artbooks, comics, or other supplementary materials, but let's have some fun 'til then...
  • Moonshine Mob:
    • The Spider: Louie Longlegs.
    • The Lightbug: Lola Limelight, Bugsy Hart.
    • The Anteater: Sammy Schnozz, Anthony Anteater.
    • Snail Boss: Don Molluscini.
  • Howling Aces:
  • Mortimer Freeze's Snowman: Frostbite. Al Bombinable
  • NPCS:
    • Ghost Detective: Hemlock Moans.

Mortimer Freeze began as a Santa Claus-themed boss
  • Even in the game proper, he's pretty close to a Palette Swap of your typical Santa depiction, beard and all. Accordingly, it's possible the Winter Whale was originally a bag of toys, the icicle imps were originally elves, etc.

In-story, Mortimer is the Inkwell Isles' equivalent of Santa
  • Every December he goes 'round the isles with his trusty whale loaded with toys and other fun gifts. Unless you've been naughty, in which case the whale invites you to reenact Jonah for a few hours/days...

Esther Winchester predicted the freak accident that turned her into sausages would happen
She clearly didn't do it on purpose, as she was surprised when it happened. However, she was only briefly dismayed about what happened, before getting back to the fight. Also, it's kind of suspicious that she had a floating can with a picture of herself appearing completely out of nowhere. Unless it was ready on standby.

Esther Winchester is a Loveable Rogue/Robin Hood-style outlaw
She's clearly an outlaw of some kind but owns a fairly successful-looking saloon and no one in the epilogue seems to have a problem with her. So this troper's theory is that she's a Robin Hood-style outlaw who only steals from villains. Heck, she may have even robbed the Devil himself at one point and that's why she's hiding out on Isle IV.

Each of the ingredients as a specific power

Relating to one of the above WMG in this folder, which says that the bosses' Regular modes are key to getting the ingredients.

  • Ice Sugar Cubes grant the power of astral projection. What Mortimer does in his final phase.
  • Desert Limes grant the ability to duplicate matter. Could be what Esther used to make an endless stream of sausages. The can floating could just be because Power Floats.
  • Gnome Berries. Power of animation? Could be how he got revived after being turned to stone. As a side effect, it made his stomach sentient.
  • Pineapple Mint. The pubs use it as a weapon, but it probably has other uses. IDK.
  • Distillery Dough. Isn't used in the fight with the Moonshine Mob, but is needed to act as a bonding agent for the other ingredients by making the base of the tart.

    Sequel Theories 

There will be a Cuphead 2
Since the Delicious Last Course was confirmed in 2018 after the first game of Cuphead was released in 2017, it is likely that a second Cuphead game will be announced later.

Possible Title Names for Cuphead 2
Since the second game of Cuphead was named Cuphead: The Delicious Last Course, there are some possibilities of what title names for Cuphead 3.
  • The Delicious Last Course isn't a sequel, it's a DLC. The next game would be Cuphead 2 if anything.

  • Cuphead 2 the Rescue

  • Cuphead 2 beyond Inkwell Isle

  • Cuphead in Inkwell Insanity

If there is a sequel, it will be called The Second Reel.
No real proof, I just like this one.
  • Semi-confirmed: There is a sequel for the game, but it's actually titled, "The Delicious Last Course", where Cuphead and Mugman are joined by Ms. Chalice.
    • That's a DLC Add-On for the main game, not a full sequel.

Any sequels will see Cuphead and Mugman endure into other eras of animation history.
A prequel would inversely see them in the 1920s, possibly featuring an obvious crossover, perhaps leading directly into the events of the first game, resulting in the inevitable moral, "Better the devil you know..."
  • Or, more likely, a sequel revolving around King Dice becoming a Dragon Ascendant, considering his evil laugh is heard in the ending.
    • I think it will take place in 1940s or maybe in the mid-1930's, assuming Cuphead takes place in 1930.

The plot of the sequel will be a Take That! against The Hays Code and Bowdlerization
The Big Bad will be a goody-two-shoes Moral Guardian who goes around banning "vices" like smoking and drinking, leaving it to Cuphead and Mugman to stop them.
  • This time, Cuphead and Mugman will be in debt to King Dice, who sends them out to stop the problem. When they reach the new villain, they'll have a choice to make, just like last time — but this time, it'll turn out that doing what their boss wants is in everyone's best interests this time, even though he only gives a damn about himself.

The sequel will fast forward to the Renaissance age of animation between the late 80s and early 2000s
It will likely base its art style on either Don Bluth or the cartoons often seen on Kids WB around said period, like Tiny Toons, etc.
  • May depend, ultimately, on whether the Moldenhaur brothers have a nostalgic attachment to those cartoons as well.
  • As for what would happen in this sequel, guesses of what the 80s/90s Cuphead would be like:
    • Cuphead and Mugman both have skateboards and are dressed in skater fashion.
    • The Devil is the manager of a local arcade and is either a random Jerkass who pokes the poodle, or is someone who revels in getting kids addicted to video games.
    • The soundtrack will either be 3rd Wave Ska or New Wave. Some of the final boss fights will have Industrial Metal, Nu Metal, or straight Heavy Metal music to invoke the Rotten Rock & Roll trope.

Some of the bosses will be playable characters in the sequel.
Brought Down to Normal after their Hell-given powers were taken away, of course. My personal votes are on Grim Matchstick, Captain Brineybeard, and Cala Maria, but anything's possible...
  • Sally Stageplay and Werner Werman are also likely, since they don't need to be Brought Down to Normal (Sally used mainly physical attacks and stage props in her fight, and Werner relied on his machines.)
  • What about Baroness Von Bon Bon? She mostly relied on her minions so would also not need to be Brought Down to Normal.

Chef Saltbaker will return for the sequel
To make amends, he'll serve a similar role as Porkrind. The heroes will be able to buy power-up pastries at his stand to assist in their quest. Possibly there will even be side quests involving gathering the ingredients.

Possible Boss Ideas for Future Cuphead Games

  • Fighting Giant Monsters/Kaiju in a Giant Cuphead Robot
  • Fighting a giant ape in a jungle with references to King Kong and Donkey Kong
  • Underwater battle against Shark, Whales, Kraken, or any other Sea Monster. Cala Maria helping would be cool.
  • Fighting a leprechaun or wizard over a rainbow
  • Fighting alien invaders in their UFO possibly in an airplane battle.
    • A space alien, utilizing retrofuturistic technology like ray guns and a flying saucer
  • Fighting against corrupted versions of fairy tale characters like a crazed version of Red Riding Hood riding the wolf.
  • A Wicked Witch who summons spooky scary skeletons from her cauldron in one phase, and in another has to be pursued through the sky on her broomstick via platforming.
  • Fighting a toon superhero. Possibly a Superman expy in the city or up on the rooftops.
  • A coiling, mustachioed Far East Dragon (hopefully without too many Yellow Peril elements; give it water powers if the creators really want to have Shown Their Work)
  • A snarling bear, possibly wielding a sentient hammer and sickle (after all, the 1920s were the time of the original Red Scare.)
  • A sentient jazz orchestra, bonus points for homaging Silly Symphonies' Music Land short.
  • Some classical movie monsters, perhaps an outright Monster Mash, in homage to Universal Horror.
  • An Abandoned Hospital and/or Bedlam House with sentient syringes, scalpels, gurneys, and Mad Doctor (or Depraved Dentist) at the end of it all.
  • A stereotypical hobo, with a battered top hat and a bindle stick. Possibly fought on or in a moving train.
  • A traveling salesman, who attacks with his various shoddy and shady wares.
  • A caveman fought in a cartoony prehistoric realm. Rides either a giant dinosaur or a giant stone wheel for his final phase.
  • Sentient (and ever-shapeshifting) neon signs, in homage to The Great Piggy Bank Robbery.
  • Eight bosses homaging the other eight members of Disney's Nine Old Men. May or may not be Dr. Kahl's colleagues/assistants/experiments. Just throwing out some ideas...
    • Woolie Wolfgang: A literal Wolf in Sheep's Clothing, perhaps with a strong Fairy Tale theme.
    • Warden Grimball: A tough-as-nails Knight Templar of a prison warden, bent on locking people up for the smallest infractions. May be coercing a chain gang to act as henchmen.
    • Lady Loonsberry: A sentient Tutti-Frutti hat that launches bits and pieces of herself at our heroes.
    • Jolly Jemstone: A cheerful but utterly ruthless miner who uses a monstrous Drill Tank to hunt for gems and other precious metals.
    • Farmer Frank: A farmer who chases you down on a monstrous tractor, hurling the occasional pitchfork and weed-killer grenade.
    • Mark Graveis: A zombie undertaker who loves to bury people alive. He'll fight using a shovel to hit and dig up dirt at the Cup bros, and maybe the second phase will be him digging underground to pop out at them.
  • A courtroom level where you fight a defense attorney, a prosecutor, and a judge as bosses. Expect them to be kangaroos, and expect shout-outs to Ace Attorney. The battle ends with the jury, who watch the fight from the background, holding up score cards.
  • A Bad Santa, or The Krampus.
  • A Wily Walrus. This would make room for references to Minnie the Moocher, or even Donkey Kong Country: Tropical Freeze. May be a Flunky Boss with seals and penguins, or perhaps ghost oysters.
  • Things That Go "Bump" in the Night. Wouldn't it be awesome to see Cuphead and Mugman fight the bogeyman? Maybe the battle would take place in a dark bedroom, where some kids are watching the battle from their beds in the background, cheering you on.
  • A Chess Rook, which summons Knights, Ministers, and the Queen, who attacked based on the respective movement of their pieces.
    • Interestingly enough, the Devil's casino has towers shaped like chessmen. Potential mini-boss(es) that got left on the cutting-room floor?
    • Confirmed with the King of Games.
  • A lion that summons his subjects at first (Assorted jungle animals)
  • How about some of the NPCs from the first game? Maybe they would be Brainwashed and Crazy, and mutated to make them big and scary.
    • The little scientist guy who gives you the plane blueprints would, of course, be fought in a shoot 'em-up level.
    • The turtle who gives you the black-and-white mode would, being a pacifist, not attack you directly, even when brainwashed. Instead, he would probably use psychic powers, or be a Flunky Boss. Or both.
    • The barbershop quartet could be a very fun boss, especially if they sing throughout the battle.
  • A boss that's Immune to Bullets and requires you to parry off of a weak point a certain number of times in order to beat them.
    • The King of Games is close to this, only some of the members of the court require the parry to be used in other ways.
  • A Cute Ghost Girl fought in a haunted manor. Possibly possessing the entire house for her final phase.
  • Wally Warbles' child, out for revenge over the death of his father in the first game.
  • King Dice's daughter or granddaughter, Princess Polly Hedron, a Gamer Chick with a d16 for a head who summons various stock fantasy creatures to fight you. Each face of the die represents a different emotion. Sometimes it lands on a positive emotion and drops healing items or some such.
    • Why a d16 rather than the more popular d20? It's a hexadecimal die.
  • Construction Site Equipment like pile drivers, cement mixers, bulldozers, cranes, or wrecking balls fought in a construction site.
  • A Crapsaccharine World with killer ponies as bosses.
  • A live-action animator hand, drawing stuff into the scene to attack the player.
  • Something from the 1890s, considering how much Walt liked the decade. For instance, a Gibson Girl.
  • A giant muscular wrestler as a homage to Bunny Hugged

There will be a Cuphead 3

King Dice will be redeemed in a sequel
Assuming he hasn't already been redeemed off-screen after the Devil's defeat.

The Devil will be redeemed in a sequel
Well the secret Angel and Demon boss in the DLC already seem to imply the Devil has a good side along with his evil side. Plus The Cuphead Show! showed that the Devil can actually get along with Cuphead when he isn't hunting down his soul, so maybe this will be the case for his game counterpart too. Though considering he's the Devil, his redemption will likely be a lot more difficult than Chef Saltbaker's.

The sequel will be four-player co-op.
And players three and four will be Cuphead and Mugman's long-lost sisters.

The sequel will be set in World War II, and will feature Adolf Hitler and Those Wacky Nazis (or Denser and Wackier expies of them) as villains.
Going with the above theory of each game being based off of a decade of animation, the second game will feature parodies of Wartime Cartoons to go with being set in the forties.

The sequel will feature Drive-n-Gun levels.
For is it not the duty of art to imitate life? Bonus point if, halfway through a level, the car has a completely scripted and unavoidable crash and you have to finish on foot.

The sequel will have voice acting.

New lands will be discovered.

The sequel will have the Devil and/or King Dice playable.
Possibly purely as a hidden bonus, but it would also make for a wild Unexpected Gameplay Change on the last leg of the game.

Some of the first game's bosses will return...
... but paired up with one another, creating completely new hazards and attacks. Bonus points if their new arenas go full Hailfire Peaks in combining their themes.

The sequel will have the bosses from the first game be Assist Characters.
Instead of being fully playable, the player will have the choice to swap the supers for the ability to summon the bosses to aid the brothers in battle. Each boss will perform an attack or ability that relates to their respective boss fight. For example, Cala Maria will petrify all enemies on the screen with her gorgon form, Grim Matchstick will scorch them with his flame breath, Djimmi will have his Cuphead puppet back up the brothers, and so forth.

The sequel will involve the brothers getting a Price On Their Heads.
The sequel will start off with Cuphead and Mugman accidentally offending someone very powerful who will post a reward for their deaths. The rest of the game will be about the brothers (possibly with Ms. Chalice and Elder Kettle) trying to escape the isles while fighting off the bosses who will all be looking to cash in on the reward.

Elder Kettle will be playable.
Similar to Ms. Chalice in the DLC, Elder Kettle will become fully playable in the sequel, using some kind of magic spell or potion to temporarily turn himself into a smaller, younger form to help out his charges.

    Future DLC Theories 
Whether for the main game or sequel games


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