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The Penguin Caretakers are the main antagonists of The Cuphead Show! episode Dance with Danger, they are abusive penguins that abused Mrs. Chalice in the past they also beat orphans with rulers if they don't do chores for them.
The episode takes place at the Inkwell City Orphanage, where all the orphans are forced to work without fun by washing and folding clothes, while their boss, the Chief Penguin, monitors them. Then comes in a young Ms. Chalice, pushing a trolley cart, before listening to a rhythm created by other sounds in the room, causing her to tap dance. This visually upsets the Chief Penguin before she scolds her about the number one rule of not having fun.
Then comes lunch, where everyone in the room runs out to feast, while Chalice herself, due to breaking a rule, is instead moved to another room, where she has to scrub the floors.
But keeps her rhythm for that chore, and every other, until the Chief Penguin has enough, and hangs her as a last resort. Finally having enough, Ms. Chalice divines an escape plan, by stealing all the penguins' rulers to use for a makeshift glider, until she is unable to snatch the ruler from the Head Penguin.
After the Chief Penguin catches onto her act, Chalice is able to snatch the rule and make a run for it, before hitting a dead end. The Chief Penguin then warns her not to jump out and gives her to the count of three to step away, but she rebels after going through with her abuse. She flies out the window, much to her and the other penguins' shock.
Ms. Chalice then remains to glide, until she hits a billboard and falls into a garbage can in an alleyway, where she finds a leftover can of beans to eat when she gets hungry. However, the only "bean" inside is a bug that then crawl on her hand, much to her disgust as she then tap-dances out onto the street, until a passing gentleman tips her a coin. Here, Chalice then gets an idea to tap-dance for money, as she then sings a song about how she can get anything by charming people.
When she grows up, she continues to charm others, until she ends her song in the middle of a road, where she gets hit clean by a trolley. She then wakes up in Inkwell Hell, to find out that she is now a ghost, before the Devil greets her, and looks through her life record of her charming people into giving her things for free. Through her singing and tap dancing.
When Ms. Chalice then attempts to leave, the Devil blocks her with a wall of fire, and tells her that without her feet, she is unable to tap dance. When Chalice questions a way to be resurrected, the Devil then offers her a second chance, where now, she has the ability to transform into her living and spectral form at will. Ms. Chalice then makes a deal with the Devil, transforming her back to her regular self, before being prompted to hand the Devil her wallet. Here the Devil teleports Ms. Chalice back to reality, before Henchman questions the absence of his own wallet. (likely presuming that Ms. Chalice stole his wallet behind their backs)
Back in Inkwell Isle, many citizens are checking over the body of Ms. Chalice, before she comes back to life, scaring all of them. As soon as she comes back, she finds an apple at a fruit stand, before a Bee Cop chases her, only to lose her once Chalice hides on the side of an optician's. That where she then charms the Screwdriver Clerk into giving her a free pair of sunglasses, and how Cuphead and Mugman soon knew about her.
As she's finished telling about her backstory, the elevator soon stops as Henchman then tells her that they have arrived at Inkwell Hell, where she steps into the Devil's throne room. The Devil requests her to betray Cuphead and Mugman for real, much to her shock.
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Cuphead The Cuphead Show!
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