Of course the Devil owns a casino the sum of all of the numbers on a roulette, a famous casino game, is 666.
Also, many religions consider gambling to be sinful. Considering they cater heavily to the common cardinal sins of greed, gluttony, lust, and pride, is it any wonder that the Devil makes one his headquarters?
It's also a reference to his M.O. "The House Always Wins", after all, and the Devil is perfectly happy to rig the games to win souls.
The game also emulates the style of the late 20s and the early 30s around the time of The Great Depression. Back then, gambling would have been seen as an extremely prideful show of excess, with the economy in such a horrific state, making the "gambling is bad" message era-appropriate.
Get to the last phase of "All Bets Are Off!" and King Dice will finally fight by making lines of cards march out of his sleeves. And it's nothing but Aces. So he's literally a Card-Carrying Villain with an Ace up his sleeve!
The Devil's first form has an attack where he grows goat horns and hooves, another where his head turns into a snake, and one more where he grows four more arms and tears his head off to become a smaller spider. In The Bible, goats represented evil, and as for the snake, the Devil himself took the form of one to tempt Adam and Eve. All three forms could also be a reference to demon princes, with the goat being Baphomet, the snake being Lucifer, and the spider being Baal.
The name of the setting is Inkwell Isles. The first Fleischer cartoon that combined live action and animation was "Out of the Inkwell".
The player can choose whether or not to join the Devil. Most cartoon characters pre-Hays code didn't have to conform to a standard of morality. Thus, while Cuphead and Mugman can get called out for gambling, they don't have to be role models for children.
Djimmi being based on Arabian genies but having heavy Egyptian theming is probably meant to invoke the theme parks' approach to foreign cultures remember the Inkwell Isle II is actually a theme park. Imagine an entrepreneur from the 30s being told to design a genie set and responding "Arabia and Egypt are basically the same place, right?"
Djimmi smoking a pipe throughout his boss fight may seem sort of inexplicable, considering it doesn't really fit the rest of his design and it's barely used during the fight, but remember that in mythology, genies were said to be created from smoke and fire.
Elsewhere in the game, parrying ghosts gets rid of them. Here you're getting rid of the ghost by making them no longer a ghost.
During the fight with Werner Werman, you can see the cat, Katzenwagen, looking into the mouse hole. At first, you'd think this is just meant to invoke the classic Tom and Jerry scenario. Upon learning it's a mech suit, it all makes sense; it was on standby mode, ready in case Werner's fight went south.
It could also double as another reference to Moby-Dick, in which the whale swallowed a bunch of seamen.
Of all the King's Court members to choose from, why does King Dice personally appear in Mister Wheezy's match (as an arm and leg cameo)? Because they're both designed after the same person Cab Calloway, that is! The connection also makes Dice stepping on Wheezy at the end of the match darkly funnier in a way.
King Dice's design is very clever, particularly the placement of the pips on his die head:
His nose is the 1 of the die that makes up his head. note You can even confirm this using the fact that the six is on the back of his head; all standard six-sided die have their opposing faces' value sum to 7. This could be a subtle allusion to "snake eyes" (rolling two ones), which is not only the roll that causes Cuphead and Mugman to lose the craps game, but also a way of calling him a metaphorical snake (as in, an untrustworthy person).
Furthermore, notice the pips on King Dice's head. The front and back of his head each have 1 and 6 pips respectively, the sides of his head have 3 and 4 pips, and on top of his head there are 5 pips, which would leave the 2 side on the bottom of his head... but of course, you can never see it because the bottom side is where his body is. Or at least, not the side itself; you can still see the 2 pips... which serve as the buttons on his vest.
Pink is a vibrant color, perfect for showing off MDHR's colorization process, which would have been expensive and cutting-edge at the time, so the parry mechanic calls attention to it.
A related thought process probably went into making the game Nintendo Hard: mimicking the style of the 20s and 30s is a difficult and infamously expensive process; all that effort would be wasted on bosses and levels that are only played once. By making them difficult, the amount of time the player spends in each level (either beating it the first time or perfecting the run) goes up exponentially.
As these two players note, Bonbon is an allusion to Marie Antoinette (being able to decapitate and throw her head at Cuphead), along with the saying misattributed to her, "let them eat cake" (her castle is the cake).
Those mosquitoes from "Treetop Trouble" that are helping Cuphead and Mugman defeat their level's miniboss aren't doing it just to be nice and subvert stereotypes. The boss is a giant dragonfly and, in reality, mosquitoes are the ideal prey of the common dragonfly species. So, the boss has either enslaved them or is about to eat them later, but not doing so, because it has to defend its territory first.
The ending to "Aviary Action!" also makes sense, following the upper example. Wally is at least partially based on the common cuckoo, which typically exploits other birds to raise their offspring (like Willy) and might attack them if they refuse or fail to do so properly. Said birds are mostly songbirds, which is what the medics happen to resemble and they are, in fact, doing Wally's bidding by helping him stay in the fight. It is little to no surprise that the medic birds ended up turning on him, as the blame for Wally's death would still mostly fall on the player.
How do Cuphead and Mugman come back after being killed in a battle? By Negative Continuity, a trope commonly found in cartoons like the ones that the game was based on!
Of course Mangosteen, being a living 8 ball, would be fought on the 8 space of King Dice's board.
Mangosteen appears to be an 8-ball made up largely of ink or something similar, as evidenced by his knockout animation. Kind of like a real-life Magic 8-Ball.
The acts of Sally Stageplay's stageplay are out of order. The first and second phases are fine, but the third and fourth phases are reversed. Logically, the fourth phase should follow the second phase, with the third phase as the final one. Not only would this complete the story (Woman gets married, raises family, dies, ascends to heaven, falls, becomes monster, is defeated; or: Woman is getting married, loses husband-to-be in chandelier accident, becomes nun, dies, ascends to heaven with husband, falls, becomes monster, is defeated), and be more fitting for a final phase considering how the other boss fights play out, but it would give her a chance to get away from Cuphead and Mugman, since she's not physically present in the monster phase. But because she's such an Attention Whore, she either reversed or scrambled them so she'd have a chance to make a Curtain Call and bask in the praise from the audience.
It's a bit unclear whether Sally's third phase is merely a cardboard cutout of her while the real Sally's offstage, or if it's literally her transformed into a cardboard cutout. Either possibility makes about as much sense. If it's the latter, however, then it's quite fitting. Sally's so narcissistic that the only superior form she could think to transform into was herself as a goddess.
The Devil's Casino is described as being on "the wrong side of the tracks" in the intro cutscene. The train tracks where you fight the Phantom Express divide the Casino from the rest of Isle 3.
The coins have Pie-Eyed shapes on them. While you could say that they just look like generic cartoon eyes, consider this: The coins are golden, and the Devil's eyes are yellow... maybe there's a hidden message behind this. Maybe not something too drastic like "The Devil is actually watching you through the coins", but something more subtle. You know what they say: Money is the root of all evil. And by using the coins to buy upgrades, you could say that, in a way, Cuphead and Mugman are using the Devil's power against him.
Only against him at the last minute. Until then, you are committing violent acts against people you don't need to, in order to get gold to get weapons to fight exactly who the Devil wants you to. You're playing right into his hands.
How do Cuphead and Mugman use the powers purchased from Porkrind? The powers come in bottles, and their heads are cups. They probably pour them in there and mix them to use the shots. As for the charms, theyre small enough to fit in a pocket, or are pins (like the extra heart charms).
The Tipsy Troop are all modeled after behaviors people exhibit when drunk or inebriated. The taller glass is lust when fighting, shamed when beaten. Whiskey is barely standing up while fighting, happy-go-lucky when defeated, and the bourbon is angry upright, almost jovial defeated.
Goopy Le Grande is modeled after the slimes from Dragon Quest, who are the first enemy encountered in any DQ game. So it makes perfect sense that Le Grande would be one of the Starter Villains.
Why is King Dice of all people the Devil's right hand man? Because King Dice embodies gambling, and most religions consider it a sin to gamble.
Why do Cuphead and Mugman still end up under the Devil's employ even when they hand over the soul contracts in the Bad Ending despite the terms of the agreement? They threw all the debtors under the bus to save themselves rather than go with the Elder Kettle's plan to save them. They committed a grievous sin and doomed themselves anyway by doing so. The Devil had a way to get his hands on their souls no matter what they decided to do.
In addition, the Devil's words in the opening says he might spare them if they collected the runaway debtor souls, not will. He never truly promised freedom. The Devil's in the details indeed.
Why do Cuphead and Mugman show fear when fighting against the Devil, but none of the other bosses? Because as Toons, they're at least partially Medium Aware. They know that even if the other bosses can "kill" them, they can't permanently harm them per the genre. The Devil, on the other hand... even in a cartoon, as the ultimate evil, he can do any number of unpleasant things to them. Scar them, torture them... imprison and/or transform them. The possibilities are... not limitless, given the G-rating of most cartoons, but still include several unpleasant options.
The boss fight with Werner Wermin indicates he defected to the British from the Austro-Hungarian army, but Werner still wears his pickelhaube helmet with pride despite teaming up with the enemy of the Germans. This may have been Werner's contract with the Devil; in exchange for Werner's soul, the Devil ensured Werner could survive the war "like rats fleeing a sinking ship".
Why wasn't it obvious that Cala Maria was a medusa? Because her snake-hair was chopped off! She replaced it with a dead octopus.
Given the number of bosses whose soul contracts are called up, the Devil's been really busy in getting nearly everyone.
Many of whom are, logically enough, the brothers' neighbors according to the book. Even if you didn't have to fight them, imagine learning that your entire community is in thrall to Satan.
Cuphead has to fight a child Willy Warbles. There also isn't a choice, since the chick will gun for you no matter what.
There's also the fact that his dad gets eaten. What'll happen to him?
What about Cuphead? He's a kid!
The implications of the bad ending. The Devil succeeded in taking Cuphead and Mugman's souls and turning them into his slaves, but then given how they were powerful enough to defeat the bosses before, the Devil could send them to round up the runaway debtors (well, the ones who are still alive) and force them to surrender their souls to the Devil. And given the debtors' amazing powers, they would be able to wreak lots of havoc on Inkwell Isle. So basically, if you chose the Bad Ending, then pretty much all of the population of Inkwell Isle will be under the servitude of the Big Bad, with a lot of them able to do major damage. Nice Job Breaking It, Hero!
On the boss's sides, they're all runaway debtors who want to be left alone. Then some upstart toons come and challenge them to a fight for the contracts. Small wonder they all put up a big fight.
They must have gone through some real anguish after they're beaten but before the contracts are destroyed, just waiting in fear and dread for the moment Cuphead might hand their souls back to the Devil.
Not every boss gets the privilege of having their soul freed and then coming back for the game's happy ending, specifically the ones that were implied to be Killed Off for Real during their Boss Battles (Goopy Le Grande and Wally Warbles). This is debatable, however, as none of the members of The Root Pack or Dr. Kahl appear, either; it is possible that some bosses held a grudge against the brothers and refused to show up at the celebration.
The Root Pack have the excuse of being a Stationary Boss, at least: it's unlikely they could leave the spot they're planted at.
Then again, so was Cagney Carnation, and he's in the ending.
Cagney can grow legs he does it in the second phase of his fight.
As explained on the character page, Wally might not have been too pleased with Cuphead and Mugman beating up his son, regardless of his soul being freed.
Goopy and Wally being Killed Off for Real are subverted, as Jake Clark (who animated the two) confirmed on Twitter that the two are still alive.
Dr. Kahl has a legitimate reason as well; it was his robot that owed the Devil his soul, not the doc himself, and you had to trash the bot in its fight. Hes probably rebuilding it, and considering the thing has to be autonomous to some level, and he was helping it in its battle, its probably his top priority.
Cala Maria spits out ghost pirates as an attack. Now, think about why she would have ghosts in her stomach. Also note that the background is full of destroyed and sunken ships.
Cala Maria is really a Gorgon in disguise as a mermaid (or rather, she's been one ever since she got into debt with the Devil).
Katzenwagen, the cat in Werner Wermen's final phase, has "imprisoned" ghost mice trapped in its mouth that it uses to attack Cuphead and Mugman. But then it's revealed that Katzenwagen is actually only a mech Werner was piloting. So why exactly is Werner using a mecha-cat to kill his own kind? Could he actually be A Nazi by Any Other Name?
Given the early 1930s setting of the game, the fact that Pickelhaube helmet Werner wears was de-spiked by the end of World War 1, how Germany was already being mocked for being overly militaristic in World War 1, and that concentration camp uniforms featured vertical stripes (rather than the horizontal of the mouse ghosts), it's more likely that Werner is mockingly designed after 'the Hun' of World War I than after Those Wacky Nazis of World War II.
The easiest explanation, given Werner's Gadgeteer Genius status, is that the ghosts are holograms and the projectiles are actually fired from Katzenwagen.
Here's one involving Beppi. After his first form is defeated, the roller coaster starts. Now look closely at the riders. THEIR HEADS HAVE X-ES FOR EYES AND MANIACAL GRINS. Who's to say Beppi didn't slaughter his own co-workers or any visitors to the park and turned them into undead riders?
Or, they could simply be dummies of the sort used for testing roller coasters before opening every day.
Supposedly, Cuphead and Mugman are kids. While it's not surprising the Devil would not care about age when making a soul contract, why would kids be allowed in a casino?
Because King Dice is enough of a sleazy manager to not care about who enters the casino so as long as they're gambling, he won't even bat an eye. Furthermore, it wouldn't be surprising if King Dice keeps an eye out for particularly irresponsible gamblers so he can get them to blow all their money away/sign their soul off to his boss.
In addition, kids are very impulsive and generally unaware of something being sketchy, meaning that for a Casino that cares not for the ethical issues of getting kids to gamble, they'd be the perfect customers.
It could also be that in Inkwell Isle, the laws are different, which allows them to gamble.
Think about the Devil and the deals he tends to make, and then consider the implications of King Dice having lost a bet. There's a real chance that he may have lost his own soul (assuming he hadn't given it to the Devil already), his position, or who knows what. While unconfirmed and a Kick the Son of a Bitch moment even if true, it may put his wrath against the boys in perspective, and his battle with them may have very well been his Last Dance.
That's something else to be considered: in King Dice's position, he was literally the Devil's right-hand man, yet he made a deal with his boss regarding whether or not Cuphead and Mugman would collect from the debtors, and obviously the Devil deals in souls. King Dice went so far as to betray the Devil when the boys arrived with all the contracts, refusing to let them meet, just to ensure he wouldn't lose. It begs the question just what would the Devil have had to cough up if he had lost?
An NPC in the first island strongly implies that all the coins scattered throughout the game are his. He doesn't seem to mind if the boys find a couple of them, but if the player goes for 100% Completion, you've collected up the poor guy's fortune and likely spent it all on upgrades, meaning he's unlikely to get any of it back.
Not quite. He seems happy to let anyone collect his coins, so long as the Devil doesn't get his hands on them.
The mixture between 20s American (just about) culture mixed with ancient Greek imagery (what with all the bosses being modeled after Greek monsters plus Greek architecture) implies a type of Anachronism Stew going on.