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On Inkwell Isle, Cuphead and his brother, Mugman, are two fun-loving children who live under the watchful eye of Elder Kettle. Despite Elder Kettle's warnings, the brothers wander off to the Devil's Casino and begin playing craps. When they go on a winning streak, the Devil appears and makes a deal, offering to give them all the money in the casino if they win the next roll and threatening to take their souls if they lose. Cuphead accepts the offer and loses by rolling snake eyes. As he and Mugman beg for mercy, the Devil offers them another deal: if they can collect the "soul contracts" from his runaway debtors by midnight the next day, the brothers will be spared. Cuphead and Mugman return to Elder Kettle, who gives them a magic potion that allows them to fire blasts of energy from their fingers, but also warns them that the debtors may not turn in their soul contracts willingly.

The brothers travel around the neighboring Inkwell Isles, fighting the debtors in order to obtain their contracts. As they enter the second Isle, Elder Kettle notices that the duo are getting stronger from their battles, and urges them to "do the right thing" when they meet the Devil. After Cuphead and Mugman enter the third Isle, King Dice, the casino's manager, reports the cup brothers' progress to the Devil. King Dice soon becomes suspicious that they may be up to something, to which the Devil replies that there is nothing to worry about; if they were to try anything, he would be waiting for them.