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The various minor characters, both friend and foe, that the cups run into during their travels on the Inkwell Isles.
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Allies and Other Characters

    Porkrind 
https://static.tvtropes.org/pmwiki/pub/images/porkrind.png
"You gots to equip those new purchases if you want to use them. Look at your equip card, ya bums!"
A pig who runs the shop where you can buy power ups.
  • Expy:
  • Eyepatch of Power: He has an eyepatch, and although we never see him get in on the action, he does look pretty tough and burly.
  • Face of a Thug: Being a pig with a large physique, eyepatch, dastardly-looking mustache, gruff voice, menacing smile (especially on his icon), and some black on his outfit, he looks like an Obviously Evil cartoon villain, but he actually helps the cups by selling them useful power-ups.
  • Grail in the Garbage: Most of Porkrind's wares are commonly-found items like drinks and cheap knickknacks, but The Delicious Last Course adds the Broken Relic to his rotation. Seemingly useless at first glance, it turns out to be a cursed artifact with incredible power locked away inside it.
  • Jerk with a Heart of Gold: He rather rudely tells the cups off for not immediately equipping what they bought from him when you exit his shop for the first time, but he only does it once and he's an indispensable ally for the rest of the game, seeing as he sells the cups their weapons and gear.
  • Mobile Kiosk: His store is on wheels, allowing him to move it across the isles. It's not explained how he got to Inkwell Isle 4, which is a good distance over the ocean from the main isles, but his store there is notably a fixed stand rather than the wheeled store he has in the other isles.
  • Pig Man: An anthropomorphic pig.
  • A Pig Named "Porkchop": A pig named Porkrind.
  • Shout-Out: His gravelly "Welcome!" is one to the shopkeep from Resident Evil 4.
  • What the Hell Is That Accent?: In his voice lines, he seems to have a German or Russian accent. However, his written dialogue after you leave his shop for the first time gives him more of a Bronx accent.

    Canteen Hughes 
https://static.tvtropes.org/pmwiki/pub/images/canteen_hughes.png
"Your aeroplanes are now equipped with mini-bombs, switch your weapons anytime during battle!"
A canteen who's responsible for maintaining and upgrading the cups' airplanes, as well as teaching them how to fly a plane.
  • Ace Pilot: He's good enough to keep up with the Howling Aces, while keeping the plane steady enough that the Cups can walk on its wings!
  • Ascended Extra: The DLC promotes him from just a tutorial character into taking an active role in the fight against the Howling Aces, flying the plane Cuphead and co. use as a platform.
  • Funny Background Event: During the Howling Aces fight, he actively reacts to whatever's going on, occasionally glancing in the direction of the boss while flying his plane around, clapping his hands when the next phase of the boss appears, and panicking if the player takes damage or gets killed.
  • Gadgeteer Genius: Implied to have made the planes the cups ride, and in Isle 2 he fits the planes with a bomb upgrade.

    Quadratus 
A mysterious being who keeps track of how many times the cups have failed.

    The Four Mel Arrangement 

Voiced by: Shoptimus Prime

A barbershop quartet (of barber poles) whose fourth member has gone missing.

    The Calix Animi 
An ancient order of heroes alluded to in the ruins of Rugged Ridge.
  • Ambiguous Situation: Given they are only referenced in one level, it's difficult to say if they are even around in the present day or even what happened to them in the first place.
  • Cavalry of the Dead: Ms. Chalice's Super Art 3 has her summon the spirits of the Calix Animi to lay waste to her opponents.
  • Gratuitous Latin: "Brave / courageous cups" or "living / animated cups," depending on your interpretation, both of which fit them well.
  • Greater-Scope Paragon: They seem to be the old heroes of Inkwell Isle.

    Inkwell Isle 1 Residents 
The NPCs that reside within the first Inkwell Isle, consisting of the apple-headed Mac, Quint the coin man, axe-headed Chip and Angel the fishing goldfish.
  • Doesn't Trust Those Guys: Quint hides his money around the Isles because he doesn't trust banks.
  • Hero of Another Story: Apparently Chip is on his own quest to take down the Devil's runaway debtors.
  • MsExposition: Angel's role is to tell you that you can only hit the ghosts in the Mausoleums by parrying them.
  • Punny Name:
    • Mac is likely named after the McIntosh variety of apple.
    • Chip is named for the wood chips that go flying when a tree is cut with an axe, and also for the chips that can form in the blade over time.

    Inkwell Isle 2 Fairgoers 
The NPCs that appear in the second Inkwell Isle, consisting of Ginger the cookie girl, Lucien the scholarly lightbulb, and Buster the juggler.

    Inkwell Isle 3 Cityfolk 
The NPCs that you meet in the third Inkwell Isle, consisting of Cora the pirate girl, music rivals Wolfgang the radio and Ludwig the phonograph, Silverworth the socialite fork, and Tully the pacifistic turtle.
  • Cosmetic Award: Three questlines in the isle reward these:
    • Silverworth judges the player characters for their life status (i.e., your number of A- and above ranks), and once he deems the cups high class (once you get 15 of those), he rewards the player with the 2-Strip filter, which renders the whole game in Technicolor-style coloring.
    • Tully preaches the path of pacifism, and once you get a P-rank in all the Run n' Gun stages by not killing any of the enemies in those, he rewards the player with the Black & White filter.
    • Continuously going back and forth between Wolfgang and Ludwig's arguments on musical minimalism vs maximalism will eventually award you with the option to switch the overworld themes to their piano versions, which you can toggle by talking to Ludwig (piano versions) or Wolfgang (band versions).
  • Named After Somebody Famous: Ludwig and Wolfgang, the two musical chaps.

    Inkwell Isle 4 Townspeople 
The residents of the DLC island, consisting of Newsie Cat, Cactus Girl, Ghost Detective, Lantern, Shovel, and Pickaxe.

  • Animate Inanimate Object: Lantern, Shovel, and Pickaxe, the three contestants of the climbing contest, are anthropomorphic versions of the objects they're named after.
  • Cactus Person: Cactus Girl, an anthropomorphic cactus living in the desert area by Esther Winchester's fight.
  • Cute Kitten: Newsie Cat is a young cat with a very cute design.
  • Expy: Newsie Cat looks a lot like Felix the Cat.
  • Extra! Extra! Read All About It!: As his name indicates, Newsy Cat is a classic newspaper boy.

Enemies

Run 'n' Gun Enemies

    General 
The various, basic enemies and mini-bosses found in the various stretches in between the bosses. They run a wide spectrum of shapes and sizes, but they are relentless enough to be large threats in their own right.
  • Badass Normal: The majority have no real powers or transformations to speak of, but they can still wallop you something fierce if you let them.
  • Game-Over Man: Like the bosses, losing in their respective stages will have the respective Mooks mocking you with a pun related to your defeat. The Cyclops in Rugged Ridge gets one separate from the other enemies in that level.
  • Giant Space Flea from Nowhere: None of these guys have any real bearing on the plot at large, they aren't under the servitude of the Devil or Debtors as far as we know, and are mostly used as fodder material whenever a player wants to take a break from fighting bosses or get more coins for better weapons and items.
  • Hair-Trigger Temper: For the most part, it seems that all of these enemies want to kill the cups simply because they had the nerve to set foot in their territory.
  • Hard Levels, Easy Bosses: In particular because there's no way to change the difficulty for these stages besides switching from two players to one. Run 'n' Gun levels are merciless challenges, but the mini-bosses have fairly simple attack patterns to avoid.
  • Killer Rabbit: No matter how cartoony or cute these guys appear, they will take you down if they can.
  • Mercy Rewarded: Perform a Pacifist Run on any of the levels, and you'll be rewarded with the P-Rank, the highest ranking one can get on the Run n' Gun stages.
  • Pacifist Run: It's possible to get through all of these levels without killing any enemies. It is not, however, easy.
  • Respawning Enemies: Some stages have enemies (sometimes literally) jump out at you without end until you move on to the next section of the level.
  • Skippable Boss: All of the minibosses are skippable in some matter, to facilitate the Pacifist Rank. Some can be smoke bombed past, some can be skipped with clever parries, and sometimes you can just take damage and let your Mercy Invincibility do the rest.

    Forest Follies' Foes 
https://static.tvtropes.org/pmwiki/pub/images/forestfollies.png
"Nowhere to run, nowhere to go — this forest is yer foe!"
The inhabitants of the woods leading to Goopy le Grande.
  • Blob Monster: The tiny slimes with limbs that run back and forth, and respawn after being defeated.
  • Foul Flower: The most basic enemies on this level are humanoid flowers that run after the cups to harm them the moment they appear. There are also purple tulips that fire exploding beans.
  • The Goomba: The flower people that parachute from the sky are the most basic enemies on this level and can be defeated in several shots.
  • Incendiary Exponent: The purple tulips fire purple beans that explode into flames when they hit the ground.
  • Invincible Minor Minion: There are Piranha Plant-esque plants that jump from bottomless pits as a stage hazard, which can't be destroyed.
  • The Lost Woods: The level runs through a woodland area where the player must platform along tree stumps and logs, jump over pits filled with thorny vines, and fight a horde of animated flowers, mushrooms, tiny slimes, jumping carnivorous plants, and dive-bombing acorns.
  • Man-Eating Plant: Giant black flytrap-esque plants appear as stage hazards.
  • Mook Maker: The Acorn Maker, a furnace-like machine endlessly cranked by a single flower enemy.
  • Plant Person: With the exception of the slimes and the mechanical Acorn Maker, all of the enemies are animated plants (or animated fungi, or living seeds).
  • Reviving Enemy: The tiny slimes that run about fall into a puddle when shot once, but reform themselves a second later to continue running around.

    Treetop Trouble's Terrors 
https://static.tvtropes.org/pmwiki/pub/images/treetoptroubles.png
"Who invited you into our tree? Only members are welcome, ya see?"
A bunch of insects and other creatures that live in a hollowed-out tree and the canopy above.
  • Airborne Mook: The beetle enemies constantly fly mid-air.
  • Big Creepy-Crawlies: The level is populated with tumbling ladybugs, fanged beetles, helpful mosquitoes, and a giant dragonfly as a miniboss.
  • Dreadful Dragonfly: A giant fire-breathing dragonfly serves as the Mini-Boss in this level.
  • Fireballs: The giant dragonfly mini-boss breathes fireballs at Cuphead and destroys the mosquito platforms floating around.
  • Helpful Mook: The mosquitoes that hold up leaves for the cups to walk on. Likely because they're so helpful to the cups, they get shot out of the air by the mini-boss as soon as they are leapt on.
  • Invincible Minor Minion: The woodpeckers that peck into the ramp of the first section.
  • Mind Screw: Did Cuphead enter a Macro Zone by shrinking, or is he the same size and it's just a big tree? There are sawed logs that spit projectiles at him, but there are also giant woodpeckers and bugs.
  • Pun-Based Creature:
    • The ladybugs seen in the level are rolling or bouncing down the ramps during the first area of the level. In other words, they're literal "tumble bugs."
    • The large dragonfly miniboss spits fireballs like a dragon. It's a dragon-fly.
  • Temporary Platform: The last stretch requires the player to travel across a series of leaves held in the air by mosquitoes, which are shot out of the sky by the fire-breathing miniboss as soon as the player lands on them.
  • Tree Trunk Tour: Their level sees the player climbing up and through a gigantic, hollow tree, facing a variety of insects, living logs and gigantic woodpeckers on the way.
  • When Trees Attack: Living wood logs appear as enemies in this level.

    Funfair Fever's Fighters 
https://static.tvtropes.org/pmwiki/pub/images/funfairfever.png
"You did look foolish today, but clown tryouts are next week."
The entertainers and living treats and trinkets that reside within the circus of Isle Two.
  • Airborne Mook: Both the magicians and the balloons count as this. The former is stationary — except when they teleport away from your attacks — while the latter can move, but only in one direction, and aren't especially interested in attacking you.
  • Animate Inanimate Object: The walking trampoline actually seems to think it's a dog, given how it barks at you. Additionally, the other enemies are a bunch of balloons with faces, a row of frowning cannons and a shotgun-totting shooting gallery as a miniboss.
  • Anthropomorphic Food: A giant dancing hotdog appears as a Mini-Boss at the end of the level. There are also giant pretzels that hop up and down, serving as obstacles.
  • Edible Ammunition: The dancing hotdog mini-boss at the end of the level fires blobs of mustard, ketchup, and relish at you.
  • Helpful Mook: The walking trampoline is absolutely necessary for getting past the barriers in the first tent.
  • Magicians Are Wizards: Lots of disappearing magicians float around firing circles of magic at the cups.
  • Spread Shot: The balloons that float past you explode if damaged, shooting out bullets in all directions.
  • Villainous Harlequin: The vertical rows of clowns under one of the big top tents. One of the enemies is also a tiny clown on a ball that rolls around a tiny area. Destroying the clown only makes the ball itself roll around faster.

    Funhouse Frazzle's Frights 
https://static.tvtropes.org/pmwiki/pub/images/funhousefrazzle.png
"We ain't toyin' around with you, now scram!"
A bunch of bizarre oddities living within the even weirder carnival funhouse.
  • Action Bomb: Small rocket enemies who appear in the second gauntlet will try to ram themselves into you and blow up, or if you happen to be under/above them from the gravity-reversing cards, then they'll rocket themselves towards you instead.
  • Eldritch Location: The tent where the toys live in starts out normal enough, but then the cups run through what looks like an obviously fake cardboard set of the moon before they find a one-eyed wall blocking their path. Getting past that opens the way to a house filled with doors, swirling hallways, and stairs going in nonsensical directions. After that, they go through a place where giant musical instruments and cardboard eyeballs are suspended in a background of clouds, rainbows, and spinning wheels before it abruptly ends and turns back into a normal hallway when they get past the exit. Could be a case of Maybe Magic, Maybe Mundane, as mostly everything is a cardboard cutout being hung by strings in the background, with a pile of unused props stuffed in a corner being seen at the end of the level.
  • Evil Laugh: The jack-in-the-box toys let out a childlike laugh when appearing before sending their spiked hat out to home in on the player.
  • Expy: The tuba enemies are quite clearly modelled after the king baritone sax from the Silly Symphonies short "Music Land."
  • Invincible Minor Minion: The clown-cars from the first half. The gravity-reversing cards are absolutely essential to escaping them.
  • Living Structure Monster: The living walls that need to be defeated to head deeper into the level.
  • Living Toy: Giant wind-up ducks, rows of toy cars, jacks with eyes at the ends of them, and a jack-in-the-box make up most of the enemies in the level
  • Lovecraft Lite: The Living Structure Monster mini-bosses are this in spades, being living walls that serve as the entrance and exit to the weirder parts of the funhouse that not only fire lips at you from bike horns, but also spit lines of clown-cars and use their Overly-Long Tongue to attack. Shooting their eyes actually takes longer to defeat them; instead, running into their gaping mouths kills them just too.
  • Musical Assassin: The last leg pits our heroes against sentient tubas that attack with sound effects.
  • Stealth Pun: The giant ducks can be avoided by crouching. In other words, you can duck under the ducks!
  • Villainous Harlequin: The four-way jack-in-the-boxes with eyeballs in the center of their bodies.

    Rugged Ridge's Rogues 
https://static.tvtropes.org/pmwiki/pub/images/ruggedridge.png
"You'll never best a bluff, persevere a peak, or curb a cliff — just give up now!"
"Fee fi fo fum, I'm the guardian of this ruined land."
Enemies that made their home in a particularly precarious set of mountains with an interesting secret.
  • Advancing Boss of Doom: The giant gorilla-like cyclops at the end. Apparently he's the chief guardian of the ruins.
  • Classical Cyclops: A grey-skinned cyclops with a single centrally-positioned horn appears as an Advancing Boss of Doom, starting to chase the player halfway through and destroying any platform in its way.
  • Death Mountain: Rugged Ridge is a treacherous mountain area featuring plentiful pits and slopes, and home to a variety of enemies based on both actual mountain wildlife and mythical creatures associated with mountainous areas.
  • Evil Living Flames: The animated flames that circle around in the air in the first half of the level, chuckling nastily.
  • Fauns and Satyrs: Satyrs appear in the third quarter of the level.
  • Gameplay and Story Segregation: The rabble is hostile toward Ms. Chalice, even though they're guarding what's implied to be her home when she was alive.
  • The Goomba: The satyrs are basically this, dying in one hit and having no special abilities other than being able to run (slightly) faster than our heroes. Interestingly enough, they only appear in the second half, mostly to provide backup for tougher Mooks.
  • Gratuitous Latin: When the cups come upon the ruined castle, they see a plaque of a shield bearing a teacup and some kitchen utensils, below which is an inscription that says "Calix Animī" (which, when translated from Latin, means "The Courageous Cups" or "The Animated Cups").
  • Hailfire Peaks: One part steep mountain range, one part ruined fairy tale castle in that mountain range.
  • Improbable Use of a Weapon: The mountain goat miners use their pickaxes as Battle Boomerang projectiles.
  • Muck Monster: During the ancient elevator sequence, a steady stream of humanoids made out of mud rises out of the ground to attack the cups.
  • Our Dragons Are Different: During the ancient elevator sequence, tiny dragons constantly appear to spew fireballs at the cups.
  • Rock Monster: The lion heads made of rocks appear as more dangerous enemies, blowing the cups back with their roars.
  • The Unfought: The Cyclops. Outrun him all the way through and he falls into the Bottomless Pit all by himself.
  • Unique Enemy: The Cyclops is the only non-boss enemy in the game to get his own individual game-over card.
  • Wham Episode: Somewhat; at first, the stage is simple — just a fairly treacherous mountain range — but, halfway through, the cups go down an ancient elevator and more mythical creatures begin to serve as enemies. Then they go into the ruined castle grounds and find out it was the home of the Legendary Chalice back when she was alive, via a statue of her in the background, and that most of the enemies are guarding what's left of her home. There's also a statue of what appears to be the Elder Kettle, or at least a direct ancestor of his.

    Perilous Piers' Pests 
https://static.tvtropes.org/pmwiki/pub/images/perilouspiers.png
"The Fish Federation and the Crustacean Nation are victorious once again!"
An army of angry sea life that swim along the pier of Isle Three.
  • Airborne Mook: The flying fish are constantly airborne.
  • Determinator: The lobster mini-boss of the third area will always come back ten seconds later, no matter how many times you beat him, until you get to the boat.
  • Fiendish Fish: The flying fish are some of the most common enemies in this level.
  • Flying Seafood Special: The flying fish and starfish trapped within bubbles that serve as airborne obstacles, among others.
  • Giant Enemy Crab: The large crabs with boxes on their heads in the second area and a vicious lobster in the third area.
  • Helpful Mook: The buoys that you parry to gain extra distance, and the octopus that takes you to the end of the level. It even spits cannonballs for you!
  • Temporary Platform: One stretch requires the player to travel across a series of wooden platforms held up by octopus tentacles, which begin to sink into the water as soon as the player lands on them.

The Mausoleums

    The Spectre Syndicate 
https://static.tvtropes.org/pmwiki/pub/images/mausoleum.png
"Is success achievable? Not when we are this un-boo-lievable!"
A gang of ghosts that hang around the Mausoleums of Inkwell Isle, trapping any unfortunate soul to wander inside.
  • Asteroids Monster: The third Mausoleum has large ghosts that move slowly, but split into two smaller and faster ghosts when parried.
  • Bedsheet Ghost: They all have this appearance.
  • Colour-Coded for Your Convenience: Their pink colouring hints that they're all parryable, and this is vital since parrying is the only way to beat them.
  • Ghostly Gape: Nearly all of them have empty eye sockets.
  • Kung Fu-Proof Mook: As an NPC outside the first mausoleum will warn you, none of your usual attacks will work on them; the only way to kill them is by parrying. By the same token, there's nothing they can do to hurt you — except by getting to the urn where the Legendary Chalice is imprisoned in the center of the stage.
  • Night of the Living Mooks: Ghost enemies who have no goal but to capture souls in the Mausoleum.
  • Touch the Intangible: You can only interact with them by parrying. Anything else will just go straight through them.

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