While heading down to Inkwell Hell, Ms. Chalice has a flashback of her backstory. Many years ago, she used to live in an orphanage under the strict authority of its penguin caretakers. Unhappy with her life in the orphanage, especially when the caretakers refuse to let her express her love of dancing, she escapes and ends up in an alley. While searching for food, she gets grossed out by a bug crawling on her arm, causing her to perform a short, unexpected dance, making a passerby give her some money for being so charming. Now finding purpose in her life, Chalice spends the next several years charming the citizens of Inkwell Isle to get things for free and look out for being number one. One day, during a performance, she is suddenly run over by a trolley, killing her and sending her soul to Inkwell Hell, where she meets the Devil. Chalice is swayed by the Devil to make a deal with him where, if she does a random favor for him, she can get her body back. After the deal is made, Chalice comes back to life, along with getting the ability to also assume a ghostly form, and proceeds to rob the optical store, revealing that she made her deal with the Devil on the same day she met Cuphead and Mugman, which was also the day she started to look out for someone who wasn't number one. After Chalice's flashback concludes, she arrives at Inkwell Hell and meets up with the Devil, who reminds her of the random favor she promised to fulfill. However, due to the Devil having learned that she is friends with Cuphead and Mugman, he reveals that the favor he has made is to betray them, much to Chalice's horror.
(Synopsis courtesy of Wikipedia)

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